Scopolamine (transdermal): Difference between revisions

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{{CMG}}
{{DrugProjectFormSinglePage
|authorTag={{VP}}<!--Overview-->
|genericName=Scopolamine
|aOrAn=an
|drugClass=[[anticholinergic]] agent
|indicationType=treatment
|indication=[[motion sickness]], post operative [[nausea]] and [[vomiting]]
|adverseReactions=[[dry mouth]], [[dizziness]], [[somnolence]], [[urinary retention]], agitation, [[visual impairment]], [[confusion]], [[mydriasis]] and [[pharyngitis]]


{{EH}}
<!--Black Box Warning-->
|blackBoxWarningTitle=Title
|blackBoxWarningBody=<i><span style="color:#FF0000;">ConditionName: </span></i>


:''The fictional truth drug [[Hyoscine-pentothal]] does not describe real hyoscine accurately.''
* Content
{{drugbox
 
| IUPAC_name = (-)-(''S'')-3-Hydroxy-2-phenyl-propionic acid (1''R'',2''R'',4''S'',7''S'',9''S'')- 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.0<sup>2,4</sup>]non-7-yl ester
<!--Adult Indications and Dosage-->
| image = L-Scopolamin.svg
 
| width = 178px
<!--FDA-Labeled Indications and Dosage (Adult)-->
| CAS_number = 51-34-3
|fdaLIADAdult======Motion Sickness=====
| ATC_prefix = A04
 
| ATC_suffix = AD01
*Initiation of Therapy
| ATC_supplemental = {{ATC|N05|CM05}}, {{ATC|S01|FA02}}
:*To prevent the nausea and vomiting associated with [[motion sickness]], one Transderm Scōp® patch (formulated to deliver approximately 1mg of scopolamine over 3 days) should be applied to the hairless area behind one ear at least 4 hours before the antiemetic effect is required.
| PubChem = 5184
 
| DrugBank = APRD00616
*Continuation of Therapy
| C=17 | H=21 | N=1 | O=4
:*If therapy is required for longer than 3 days, the first patch should be removed and a fresh one placed on the hairless area behind the other ear.
| molecular_weight = 303.353 g/mol
 
| bioavailability = 10 - 50% <ref name="pmid2762223">{{cite journal |author=Putcha L, Cintrón NM, Tsui J, Vanderploeg JM, Kramer WG |title=Pharmacokinetics and oral bioavailability of scopolamine in normal subjects |journal=Pharm. Res. |volume=6 |issue=6 |pages=481–5 |year=1989 |month=June |pmid=2762223 |doi= |url= |issn= | doi = 10.1023/A:1015916423156 <!--Retrieved from CrossRef by DOI bot--> | doi = 10.1023/A:1015916423156 <!--Retrieved from CrossRef by DOI bot-->}}</ref>
=====Post Operative Nausea and Vomiting=====
| protein_bound =  
 
| metabolism =  
*Initiation of Therapy
| elimination_half-life = 4.5 hours<ref name="pmid2762223">{{cite journal |author=Putcha L, Cintrón NM, Tsui J, Vanderploeg JM, Kramer WG |title=Pharmacokinetics and oral bioavailability of scopolamine in normal subjects |journal=Pharm. Res. |volume=6 |issue=6 |pages=481–5 |year=1989 |month=June |pmid=2762223 |doi= |url= |issn= | doi = 10.1023/A:1015916423156 <!--Retrieved from CrossRef by DOI bot--> | doi = 10.1023/A:1015916423156 <!--Retrieved from CrossRef by DOI bot-->}}</ref>
:*To prevent post operative [[nausea]] and [[vomiting]], one Transderm Scōp® patch should be applied the evening before scheduled surgery, except for caesarian section.
| pregnancy_US = C
:*For caesarian section surgery, to minimize exposure of the newborn baby to the drug, apply the patch one hour prior to caesarian section
| legal_US = Rx-only
 
| legal_UK = P
*Continuation of Therapy
| routes_of_administration = transdermal, ocular, oral, subcutaneous, intravenous
:*For perioperative use, the patch should be kept in place for 24 hours following surgery at which time it should be removed and discarded.
}}
 
'''Scopolamine''', also known as '''hyoscine''', is a [[tropane alkaloid]] [[Medication|drug]] with [[muscarinic antagonist]] effects. It is obtained from plants of the family [[Solanaceae]] (nightshades), such as [[henbane]] or jimson weed (''[[Datura]]'' species). It is among the [[secondary metabolites]] of these plants. The drug can be highly toxic and should be used in minute doses. As an example, in the treatment of motion sickness, the dose, gradually released from a transdermal patch, is only 330 micrograms (µg) per day.  An overdose can cause [[delirium]], [[delusion]]s, [[paralysis]], [[stupor]] and death.
<!--Off-Label Use and Dosage (Adult)-->
 
<!--Guideline-Supported Use (Adult)-->
|offLabelAdultGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of Scopolamine in adult patients.
 
<!--Non–Guideline-Supported Use (Adult)-->
|offLabelAdultNoGuideSupport======Excessive salivation; Prophylaxis=====
 
* Dosing Information
 
:*Transdermal scopolamine reduced salivation.<ref name="pmid2123321">{{cite journal| author=Talmi YP, Finkelstein Y, Zohar Y| title=Reduction of salivary flow with transdermal scopolamine: a four-year experience. | journal=Otolaryngol Head Neck Surg | year= 1990 | volume= 103 | issue= 4 | pages= 615-8 | pmid=2123321 | doi= | pmc= | url=http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=2123321  }} </ref>
 
<!--Pediatric Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed=There is limited information regarding <i>FDA-Labeled Use</i> of Scopolamine in pediatric patients.
 
<!--Off-Label Use and Dosage (Pediatric)-->
 
<!--Guideline-Supported Use (Pediatric)-->
|offLabelPedGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of Scopolamine in pediatric patients.
 
<!--Non–Guideline-Supported Use (Pediatric)-->
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of Scopolamine in pediatric patients.
 
<!--Contraindications-->
|contraindications=*Patients with [[angle closure glaucoma]].
 
*Persons who are [[hypersensitive]] to the drug scopolamine or other belladonna alkaloids or to any ingredient or component in the formulation or delivery system.
 
<!--Warnings-->
|warnings=====Precautions====
 
*Open Angle Glaucoma
:*Patients currently being treated for Open Angle Glaucoma
:*Glaucoma therapy in patients with [[open angle glaucoma]] should be monitored and may need to be adjusted during Transderm Scōp® use, as the [[mydriatic]] effect of scopolamine may cause an increase in [[intraocular pressure]].
:*Patients should be advised to remove the patch immediately and promptly contact a physician in the event that they experience symptoms of acute angle closure [[glaucoma]] (pain and reddening of the eyes, accompanied by [[dilated pupils]]).
 
*Temporary Dilation of the Pupil
:*Scopolamine can cause temporary dilation of the pupils and [[blurred vision]] if it comes in contact with the eyes.
:*Patients should be strongly advised to wash their hands thoroughly with soap and water immediately after handling the patch. In addition, it is important that used patches be disposed of properly to avoid contact with children or pets.
 
*Preexisting Gastrointestinal or Urinary Bladder Obstructions
:*Transderm Scōp® should be used with caution in patients with pyloric obstruction or urinary bladder neck obstruction. Caution should be exercised when administering an [[antiemetic]] or [[anticholinergic]] drug, including Transderm Scōp®, to patients suspected of having [[intestinal obstruction]].
:*Patients should be instructed to remove the patch if they develop any difficulties in urinating.
 
*History of Seizures or Psychosis
:*Transderm Scōp® should be used with caution in patients with a history of [[seizures]] or [[psychosis]] since scopolamine can potentially aggravate both disorders.
 
*Idiosyncratic Reactions
:*Idiosyncratic reactions may occur with ordinary therapeutic doses of scopolamine. The most serious of these that have been reported are: acute toxic [[psychosis]], including confusion, agitation, [[speech disorder]], [[hallucinations]], [[paranoia]], and [[delusions]].
 
*Specific Populations
 
*Pediatric
:*A safe and effective dose has not been established in the pediatric population. Children are particularly susceptible to the side effects of belladonna alkaloids; including [[mydriasis]], [[hallucinations]], [[amyblyopia]], and drug withdrawal syndrome. Neurologic and psychiatric adverse reactions, such as [[hallucinations]], [[amblyopia]] and [[mydriasis]] have also been reported when one half or one quarter of a patch has been applied.
 
*Elderly
:*Transderm Scōp® should be used with caution in the elderly because of the increased likelihood of CNS effects, such as [[hallucinations]], confusion, [[dizziness]] and drug withdrawal syndrome. Clinical trials of Transderm Scōp® did not include sufficient number of subjects aged 65 years and older to determine if they respond differently from younger subjects.
 
*Renal and Hepatic Impaired
:*Transderm Scōp® should be used with caution in individuals with impaired renal or hepatic functions because of the increased likelihood of CNS effects. Transderm Scōp® has not been studied in these populations.
 
*Safety Hazards
 
*Drowsiness
:*Since [[drowsiness]], disorientation, and confusion may occur with the use of scopolamine, patients should be warned of the possibility and cautioned against engaging in activities that require mental alertness, such as driving a motor vehicle or operating dangerous machinery.
 
*Disorienting Effects
:*Patients who expect to participate in underwater sports should be cautioned regarding the potentially disorienting effects of scopolamine.
 
*MRI Skin Burns
:*Skin burns have been reported at the patch site in several patients wearing an aluminized transdermal system during a [[Magnetic Resonance Imaging]] scan (MRI). Because Transderm Scōp® contains aluminum, it is recommended to remove the system before undergoing an [[MRI]].
 
<!--Adverse Reactions-->
 
<!--Clinical Trials Experience-->
|clinicalTrials=*Because clinical trials are conducted under widely varying conditions, adverse reaction rates observed in the clinical trials of a drug cannot be directly compared to rates in the clinical trials of another drug and may not reflect the rates observed in clinical practice.
 
=====Motion Sickness=====
 
*In motion sickness clinical studies of Transderm Scōp®, the most frequent adverse reaction was [[dry mouth]]. This occurred in about two thirds of patients on drug. A less frequent adverse drug reaction was drowsiness, which occurred in less than one sixth of patients on drug. Transient impairment of eye accommodation, including [[blurred vision]] and dilation of the [[pupils]], was also observed.
 
=====Post-Operative Nausea and Vomiting=====
 
*In a total of five clinical studies in which Transderm Scōp® was administered perioperatively to a total of 461 patients where safety was assessed, dry mouth was the most frequently reported adverse drug reaction, which occurred in approximately 29% of patients on drug. Dizziness was reported by approximately 12% of patients on drug. Other adverse drug reactions reported from these studies, with a frequency of ≥3% of patients treated with Transderm Scop and with a frequency higher than placebo were, in descending order: [[somnolence]], [[urinary retention]], agitation/restlessness, [[visual impairment]], [[confusion]], [[mydriasis]] and [[pharyngitis]] (see Table 6.1).
 
: [[File:Scopolamine01.png|thumb|none|400px|This image is provided by the National Library of Medicine.]]
 
<!--Postmarketing Experience-->
|postmarketing=*The following adverse drug reactions, further to those reported from clinical trials, have been identified during postapproval use of Transderm Scōp®. Because these reactions are reported voluntarily from a population of uncertain size, it is not always possible to reliably estimate their frequency or to confirm a definite causal relationship.
 
*In worldwide marketing with Transderm Scōp®, the following adverse drug reactions were reported by body system.
 
=====Psychiatric disorders=====
 
Acute psychosis including: [[hallucinations]] disorientation, and [[paranoia]].
 
=====Nervous system disorders=====
 
[[Headache]], [[amnesia]], coordination abnormalities, speech disorder, disturbance in attention, restlessness.
 
=====General disorders and administration site conditions=====
 
Burning sensation in the application site.
 
=====Eye disorders=====
 
Dry eyes, eye [[pruritis]], angle closure [[glaucoma]], [[amblyopia]], eyelid irritation.
 
=====Skin and subcutaneous tissue disorders=====
 
Generalized [[rash]], skin irritation, [[erythema]].
 
=====Renal and urinary disorders=====
 
[[Dysuria]].
 
=====Ear and Labyrinth Disorders=====
 
[[Vertigo]].
 
<!--Drug Interactions-->
|drugInteractions=*The absorption of oral medications may be decreased during the concurrent use of scopolamine because of decreased gastric motility and delayed gastric emptying.
 
*Scopolamine should be used with caution in patients taking other drugs that are capable of causing CNS effects such as sedatives, tranquilizers, or alcohol. Special attention should be paid to potential interactions with drugs having [[anticholinergic]] properties; e.g., other belladonna alkaloids, [[antihistamines]] (including [[meclizine]]), [[tricyclic antidepressants]], and muscle relaxants.
 
*In vitro studies indicated that the potential for scopolamine to alter the pharmacokinetics of other concomitant medications through inhibition of CYP 1A2, 2C8, 2C9, 2C19, 2D6 and 3A4 or induction of CYP 1A2 and 3A4 is low; however, in vivo studies have not been conducted.
 
<!--Use in Specific Populations-->
|useInPregnancyFDA=* '''Pregnancy Category C'''
 
*Based on data from one prospective study of Transderm Scōp® in cesarean delivery, the rate of newborn adverse events in both the Transderm Scōp® and placebo groups were the same. The rates were 10.5% (12 events in 114 newborns) in both treatment groups. None of these events were considered life threatening or drug related. [[Jaundice]] was the only adverse event occurring more frequently with Transderm Scōp® than placebo: 9 events (7.9%) versus 2 events (1.8%) (p=0.031). Jaundice, a common occurrence in newborns, resolved with ultraviolet light and did not prolong the hospital stay.
 
*There are no adequate and well-controlled studies of Transderm Scōp® use during pregnancy. In animal reproduction studies, when pregnant rats and rabbits received scopolamine hydrobromide by daily intravenous injection, no adverse effects were observed in rats. An embryotoxic effect was observed in rabbits at doses producing plasma levels approximately 100 times the levels achieved in humans using a transdermal system. Transderm Scōp® should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus and the mother.
|useInPregnancyAUS=* '''Australian Drug Evaluation Committee (ADEC) Pregnancy Category'''
 
There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Scopolamine in women who are pregnant.
|useInLaborDelivery=*During a clinical study among women undergoing cesarean section treated with Transderm Scōp® in conjunction with epidural anesthesia and opiate analgesia, no evidence of CNS depression was found in newborns. Scopolamine administered parenterally to rats and rabbits at doses higher than the dose delivered by Transderm Scōp® did not affect uterine contractions or increase the duration of labor. Scopolamine does cross the placenta.
|useInNursing=*Scopolamine is excreted in human milk. Caution should be exercised when Transderm Scōp® is administered to a nursing woman.
|useInPed=*A safe and effective dose has not been established in the pediatric population.
|useInGeri=*Transderm Scōp® should be used with caution in the elderly because of the increased likelihood of [[CNS]] effects, such as [[hallucinations]], confusion and [[dizziness]]. Clinical trials of Transderm Scōp® did not include sufficient number of subjects aged 65 years and older to determine if they respond differently from younger subjects.
|useInGender=There is no FDA guidance on the use of Scopolamine with respect to specific gender populations.
|useInRace=There is no FDA guidance on the use of Scopolamine with respect to specific racial populations.
|useInRenalImpair=There is no FDA guidance on the use of Scopolamine in patients with renal impairment.
|useInHepaticImpair=There is no FDA guidance on the use of Scopolamine in patients with hepatic impairment.
|useInReproPotential=There is no FDA guidance on the use of Scopolamine in women of reproductive potentials and males.
|useInImmunocomp=There is no FDA guidance one the use of Scopolamine in patients who are immunocompromised.
 
<!--Administration and Monitoring-->
|administration=* Transdermal
|monitoring=There is limited information regarding <i>Monitoring</i> of Scopolamine in the drug label.
 
<!--IV Compatibility-->
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of Scopolamine in the drug label.
 
<!--Overdosage-->
|overdose====Acute Overdose===
 
====Signs and Symptoms====
 
*The signs and symptoms of anticholinergic toxicity include: [[lethargy]], [[somnolence]], coma, confusion, agitation, [[hallucinations]], [[convulsion]], visual disturbance, dry flushed skin, [[dry mouth]], decreased bowel sounds, [[urinary retention]], [[tachycardia]], [[hypertension]], and [[supraventricular arrhythmias]]. These symptoms can be severe and may require medical intervention.
 
*The symptoms of overdose/toxicity due to scopolamine should be carefully distinguished from the occasionally observed syndrome of withdrawal. Although mental confusion and [[dizziness]] may be observed with both acute toxicity and withdrawal, other characteristic findings differ: [[tachyarrhythmias]], dry skin, and decreased bowel sounds suggest [[anticholinergic]] toxicity, while [[bradycardia]], [[headache]], [[nausea]] and [[abdominal cramps]], and sweating suggest post-removal withdrawal. Obtaining a careful history is crucial to making the correct diagnosis.


==Etymology==
====Management====
Scopolamine is named after the plant [[genus]] ''[[Scopolia]]''. The name "hyoscine" is from the scientific name for [[henbane]], ''Hyoscyamus niger''.


==Physiology==
*Because strategies for the management of drug overdose continually evolve, it is strongly recommended that a poison control center be contacted to obtain up-to-date information regarding the management of Transderm Scōp® patch overdose. The prescriber should be mindful that antidotes used routinely in the past may no longer be considered optimal treatment. For example, [[physostigmine]], used more or less routinely in the past, is seldom recommended for the routine management of [[anticholinergic]] syndromes.
Scopolamine acts as a competitive antagonist at specific [[muscarinic acetylcholine receptors]], specifically [[M1 receptors]]; it is thus classified as an [[anticholinergic]], or, more specifically, as an [[anti-muscarinic]] drug.  (See the article on the [[parasympathetic]] nervous system for details of this physiology.)


==Medical use==
*Until up-to-date authoritative advice is obtained, routine supportive measures should be directed to maintaining adequate respiratory and cardiac function.
In [[medicine]] scopolamine has 3 primary uses: treatment of [[nausea]] and [[motion sickness]], treatment of [[intestinal cramping]], and for ophthalmic purposes.  Use as a general depressant and adjunct to narcotic painkillers is also common.
The drug is less commonly used as a [[preanesthetic agent]] and uncommonly for some forms of [[Parkinsonism]].  Scopolamine is also used as an adjunct to narcotic analgesia, such as the product [[Twilight Sleep]] which contained [[morphine]] and scopolamine, some of the original formulations of [[Percodan]] and some European brands of [[methadone]] injection, as well as use of tablets or patches to combat nausea as well as enhance the pain-killing ability of various [[opioids]].  Scopolamine can be used as an occasional sleep aid and was available in some over the counter products in the United States for this purpose until November 1990.


===Nausea===
*In cases of toxicity remove the patch. Serious symptomatic cases of overdosage involving multiple patch applications and/or ingestion may be managed by initially ensuring the patient has an adequate airway, and supporting respiration and circulation. This should be rapidly followed by removal of all patches from the skin and the mouth. If there is evidence of patch ingestion, [[gastric lavage]], endoscopic removal of swallowed patches, or administration of [[activated charcoal]] should be considered, as indicated by the clinical situation. In any case where there is serious overdosage or signs of evolving acute toxicity, continuous monitoring of vital signs and [[ECG]], establishment of [[intravenous]] access, and administration of oxygen are all recommended.
Its use in the form of a transdermal patch to prevent [[post-operative nausea]] is perhaps its greatest current use in the US.


===Ophthalmic===
===Chronic Overdose===
The drug is used in eye drops to induce [[mydriasis]] (pupillary dilation) and [[cycloplegia]] (paralysis of the eye focusing muscle), primarily in the treatment of eye disorders that benefit from its prolonged effect, e.g. [[uveitis]], [[iritis]], [[iridocyclitis]], etc.


===Memory research===
There is limited information regarding <i>Chronic Overdose</i> of Scopolamine in the drug label.
Because of its anticholinergic effects, scopolamine has been shown to prevent the activation of [[medial temporal lobe]] structures for novel stimuli during [[working memory]] tasks.


===Nicotine addiction===
<!--Pharmacology-->
Scopolamine is being investigated for its possible usefulness alone or in conjunction with other drugs in assisting people in breaking the [[nicotine]] habit.  The mechanism by which it mitigates withdrawal symptoms appears to be at least partially different from that of [[clonidine]] meaning that the two drugs can be used together without duplicating or cancelling out the effects of each other.


===Other medical uses===
<!--Drug box 2-->
*It can be used as a depressant of the [[central nervous system]], and was formerly used as a bedtime sleep aid.
|drugBox={{drugbox2
*[[Anesthetic]]; Its use in general anesthesia is favored by some due to its [[amnesic]] effect. Scopolamine causes memory impairments to a similar degree as [[diazepam]].<ref>{{cite journal |author=Jones DM |coauthors=Jones ME, Lewis MJ, Spriggs TL. |title=Drugs and human memory: effects of low doses of nitrazepam and hyoscine on retention. |journal=Br J Clin Pharmacol. |volume=7 |issue=5 |pages=479-83 |month=May |year=1979 |pmid=475944}}</ref>
| Verifiedfields = changed
*In [[otolaryngology]] it is used to dry the upper airway (anti-sialogogue action) prior to instrumentation of the airway.
| Watchedfields = changed
*In October 2006 researchers at the US [[National Institute of Mental Health]] found that scopolamine reduced symptoms of [[depression (mood)|depression]] within a few days, and the improvement lasted for at least a week after switching to a [[placebo]].<ref>{{cite journal
| verifiedrevid = 464387972
  | last = Furey
| IUPAC_name = (–)-(''S'')-3-Hydroxy-2-phenylpropionic acid (1''R'',2''R'',4''S'',7''S'',9''S'')-9-methyl-3-oxa-9-azatricyclo[3.3.1.0<sup>2,4</sup>]non-7-yl ester
  | first = ML
| image = Scopolamine00.png
  | coauthors = Drevets, WC
| width = 200
  | title = Antidepressant efficacy of the antimuscarinic drug scopolamine: a randomized, placebo-controlled clinical trial
| image2 = Scopolamine000.gif
  | journal = Archives of General Psychiatry, vol 63, p 1121
| width2 = 225
  | volume = 63
  | pages = 1121
  | date=  October 2006
  | url = http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?orig_db=PubMed&db=PubMed&cmd=Search&term=%22Archives+of+general+psychiatry%22%5BJour%5D+AND+63%5Bvolume%5D+AND+1121%5Bpage%5D
}}</ref>
*Due to its effectiveness against [[sea-sickness]] it has become commonly used by [[Scuba set|scuba]] divers.


===Routes of administration===
<!--Clinical data-->
Scopolamine can be administered by [[transdermal patch]]es,<ref name="pmid17179250">{{cite journal |author=White PF, Tang J, Song D, ''et al'' |title=Transdermal scopolamine: an alternative to ondansetron and droperidol for the prevention of postoperative and postdischarge emetic symptoms |journal=Anesth. Analg. |volume=104 |issue=1 |pages=92-6 |year=2007 |pmid=17179250 |doi=10.1213/01.ane.0000250364.91567.72 |url=http://www.anesthesia-analgesia.org/cgi/pmidlookup?view=long&pmid=17179250}}</ref> oral, subcutaneous, [[ophthalmic]] and [[intravenous]] routes.
| tradename = Transdermscop
The transdermal patch for prevention of nausea and motion sickness employs scopolamine base. The oral, ophthalmic and intravenous forms are usually scopolamine [[hydrobromide]] (for example in [[Donnatal]]).
| Drugs.com = {{drugs.com|monograph|scopolamine}}
| pregnancy_AU = B2
| pregnancy_US = C
| legal_AU = S4
| legal_CA = Rx-only
| legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = transdermal, ocular, oral, subcutaneous, intravenous, sublingual, rectal, buccal transmucousal, intramuscular


==Recreational use==
<!--Pharmacokinetic data-->
Scopolamine, in common with the large percentage of anticholinergics which cross the blood-brain barrier such as [[diphenhydramine]], [[dicyclomine]], [[trihexyphenidyl]] and related drugs, is said to produce euphoria at and around therapeutic doses as well as to potentiate this and other effects of [[morphine]], [[methadone]], [[hydromorphone]], [[oxycodone]] and other opioids. It is therefore occasionally seen as a recreational drug. The use of medical scopolamine (most often in the form of tablets) for euphoria is uncommon but does exist and can be seen in conjunction with opioid use.  The euphoria is the result of changes in dopamine and acetylcholine levels and ratios  and appears to be related to some part of the chemical structure of the drug  and other factors known or unknown -- even closely related drugs like atropine and hyoscyamine do not produce euphoria whilst the others listed above certainly appear to.  
| bioavailability = 0.13-8% (Oral)
| protein_bound =
| metabolism = [[Hepatic]] (liver)
| excretion = [[Renal]]
| elimination_half-life = 4.5 hours<ref name="pmid2762223">{{cite journal | author = Putcha, L.; Cintrón, N. M.; Tsui, J.; Vanderploeg, J. M.; Kramer, W. G. | title = Pharmacokinetics and Oral Bioavailability of Scopolamine in Normal Subjects | journal = Pharmacology Research | volume = 6 | issue = 6 | pages = 481–485 | year = 1989 | pmid = 2762223 | doi = 10.1023/A:1015916423156 | url = }}</ref>


Another separate group of users prefer dangerously high doses, especially in the form of [[datura]] or [[belladonna]] preparations, for the deliriant and hallucinogenic effects.  The hallucinations produced by scopolamine, in common with other potent anticholinergics, are especially real-seeming and create a perception of a new world filled with frenzied, violent energy. The difference in realism of hallucinations caused by [[anticholinergics]] such as scopolamine and other [[hallucinogens]] such as the [[phenethylamines]] or dissociatives like PCP is quite large. Additionally, an overdose of scopolamine can quite often be fatal, unlike other more commonly used hallucinogens. For these reasons, naturally occurring anticholinergics are rarely used for recreational purposes.
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 51-34-3
| ATC_prefix = A04
| ATC_suffix = AD01
| ATC_supplemental = {{ATC|N05|CM05}}, {{ATC|S01|FA02}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16794
| PubChem = 5184
| IUPHAR_ligand = 330
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00747
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10194106
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DL48G20X8X
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00138
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201024


==Potential use in interrogation==
<!--Chemical data-->
The use of scopolamine as a ''[[truth drug]]'' was investigated in the 1950s by various [[intelligence agencies]], including the [[CIA]] as part of [[Project MKULTRA]]. Nazi doctor [[Josef Mengele]] experimented on scopolamine as an interrogation drug.
| C=17 | H=21 | N=1 | O=4
| molecular_weight = 303.353 g/mol
| smiles = OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34
| InChI = 1/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = STECJAGHUSJQJN-FWXGHANASA-N
}}


==Criminal use==
<!--Mechanism of Action-->
Scopolamine has been used under the name [[burundanga]], a jungle form of [[Rohypnol]] in [[Venezuela]]n and [[Thailand]] resorts in order to drug and then rob tourists.  While there are unfounded rumours that delivery mechanisms include using [[pamphlet]]s and [[Flyer (pamphlet)|flyer]]s laced with the drug, not enough is readily absorbed through the skin to have an effect. However, spiked alcoholic drinks are occasionally used. <ref>[http://www.snopes.com/horrors/mayhem/burundanga.asp Snopes Burudanga rumour page]</ref><ref>[http://travel.timesonline.co.uk/tol/life_and_style/travel/your_say/article3287518.ece The 13 best travel scams - Times Online<!-- Bot generated title -->]</ref>
|mechAction=* Scopolamine, a belladonna alkaloid, is an [[anticholinergic]] agent. Scopolamine acts: i) as a competitive inhibitor at [[postganglionic]] muscarinic receptor sites of the [[parasympathetic]] nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the [[central nervous system]] (CNS) by blocking [[cholinergic]] transmission from the [[vestibular]] nuclei to higher centers in the CNS and from the reticular formation to the vomiting center. Scopolamine can inhibit the secretion of saliva and sweat, decrease [[gastrointestinal]] secretions and motility, cause [[drowsiness]], dilate the pupils, increase heart rate, and depress motor function.


A nine part series on the drug, also known as "Colombian Devil's Breath", can be found on VBS.TV.
<!--Structure-->
|structure=* The Transderm Scōp® (scopolamine) transdermal system is a circular flat patch designed for continuous release of scopolamine following application to an area of intact skin on the head, behind the ear. Each system contains 1.5 mg of scopolamine base. Scopolamine is α -(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.02,4] non-7-yl ester. The empirical formula is C17H21NO4 and its structural formula is:


In recent years the criminal use of scopolamine has become an [[epidemic]]. Approximately fifty percent of emergency room admissions for poisoning in [[Bogotá]] have been attributed to scopolamine.<ref>Wall Street Journal, July 3, 1995</ref>
: [[File:Scopolamine02.png|thumb|none|400px|This image is provided by the National Library of Medicine.]]


Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat.
*Scopolamine is a viscous liquid that has a molecular weight of 303.35 and a pKa of 7.55-7.81. The Transderm Scōp® system is a film 0.2 mm thick and 2.5 cm2, with four layers. Proceeding from the visible surface towards the surface attached to the skin, these layers are: (1) a backing layer of tan-colored, aluminized, polyester film; (2) a drug reservoir of scopolamine, light mineral oil, and polyisobutylene; (3) a microporous polypropylene membrane that controls the rate of delivery of scopolamine from the system to the skin surface; and (4) an adhesive formulation of mineral oil, polyisobutylene, and scopolamine. A protective peel strip of siliconized polyester, which covers the adhesive layer, is removed before the system is used. The inactive components, light mineral oil (12.4 mg) and polyisobutylene (11.4 mg), are not released from the system.


Scopolamine is used criminally as a date rape drug and as an aid to robbery,<ref>http://www.sobercircle.com/index.asp?node=resources&section=articles&fileid=8| Retrieved 20/11/07</ref> the most common act being the clandestine drugging of a victim's drink<ref>http://www.sobercircle.com/index.asp?node=resources&section=articles&fileid=8| Retrieved 20/11/07</ref>. It is preferred because it induces [[anterograde amnesia]], or an inability to recall events a certain amount of time after its administration or during the time of intoxication.
<!--Pharmacodynamics-->
|PD=There is limited information regarding <i>Pharmacodynamics</i> of Scopolamine in the drug label.


==Shamanic use==
<!--Pharmacokinetics-->
In [[Colombia]] a plant admixture containing scopolamine called ''Burundanga'' has been used [[shamanism|shamanically]] for decades.
|PK=*The pharmacokinetics of scopolamine delivered via the system are due to the characteristics of both the drug and dosage form. The system is formulated to deliver in-vivo approximately 1 mg of scopolamine at an approximately constant rate to the systemic circulation over 3 days. Upon application to the postauricular skin, an initial priming dose of scopolamine is released from the adhesive layer to saturate skin-binding sites. The subsequent delivery of scopolamine to the blood is determined by the rate controlling membrane and is designed to produce stable plasma levels in a therapeutic range. Following removal of the used system, there is some degree of continued systemic absorption of scopolamine bound in the skin layers.


==Adverse effects==
*Absorption
The common side effects are related to the anticholinergic effect on [[parasympathetic]] postsynaptic receptors: dry mouth, throat and nasal passages in overdose cases progressing to impaired speech which can reach the extreme of the victim only being able to emit noises which sound like the vocalisations of a [[raccoon]], thirst, blurred vision and sensitivity to light, [[constipation]], difficulty urinating and [[tachycardia]]. Other effects include flushing and fever, as well as excitement, restlessness, hallucinations, or [[delirium]], especially with higher doses. These side effects are commonly observed with oral or parenteral uses of the drug and generally not with topical ophthalmic use. An extreme adverse reaction to ultra-high doses of drugs and other preparations containing scopolamine is temporary blindness which can last up to 72 hours
:*Scopolamine is well absorbed percutaneously. Following application to the skin behind the ear, circulating plasma levels are detected within 4 hours with peak levels being obtained, on average, within 24 hours. The average plasma concentration produced is 87 pg/mL (0.28 nM) for free scopolamine and 354 pg/mL for total scopolamine (free + conjugates).


The fever and dryness associated with scopolamine has caused some recreational users to stumble into bodies of water and drown on occasion.
*Distribution
:*The distribution of scopolamine is not well characterized. It crosses the placenta and the [[blood brain barrier]] and may be reversibly bound to plasma proteins.


Sometimes side effects of scopolamine can be mistaken for symptoms of [[cancer]] because of the nausea and [[anisocoria]] associated with brain tumors. However, scopolamine induced [[anisocoria]] clears up usually within 3 days.
*Metabolism and Excretion
:*The exact elimination pattern of scopolamine has not been determined. Following patch removal, plasma levels of scopolamine decline in a log linear fashion with an observed half-life of 9.5 hours. Less than 10% of the total dose is excreted in the urine as the parent drug and metabolites over 108 hours. Scopolamine is extensively metabolized and conjugated with less than 5% of the total dose appearing unchanged in the urine. The enzymes responsible for metabolizing scopolamine are unknown.


Use in scuba diving to prevent [[sea sickness]] has led to the discovery of another [[Adverse effect (medicine)|side effect]]. In deep water, below 50&ndash;60&nbsp;feet, some divers have reported [[pain]] in the eyes that subsides quickly if the diver ascends to a depth of 40&nbsp;feet or less. Mydriatics can precipitate an attack of [[glaucoma]] in susceptible patients, so the medication should be used with extra caution among divers who intend to go below 50&nbsp;feet.
*Drug Interaction
:*An in vitro study using human hepatocytes examined the induction of CYP1A2 and CYP3A4 by scopolamine. Scopolamine did not induce CYP1A2 and CYP3A4 isoenzymes at the concentrations up to 10 nM. In an in vitro study using human liver microsomes which evaluated the inhibition of CYP1A2, 2C8, 2C9, 2C19, 2D6 and 3A4, scopolamine did not inhibit these cytochrome P450 isoenzymes at the concentrations up to 1 mcM.


=== Drug interactions ===
<!--Nonclinical Toxicology-->
When combined with [[morphine]], it produces [[amnesia]] and a tranquilized state known as [[twilight sleep]]. Although originally used in [[obstetrics]], it is now considered dangerous for that purpose for both mother and baby.
|nonClinToxic=*No long-term studies in animals have been conducted to evaluate the carcinogenic potential of scopolamine. The mutagenic potential of scopolamine has not been evaluated.


== History ==
*Fertility studies were performed in female rats and revealed no evidence of impaired fertility or harm to the fetus due to scopolamine hydrobromide administered by daily subcutaneous injection. Maternal body weights were reduced in the highest-dose group (plasma level approximately 500 times the level achieved in humans using a transdermal system). However, fertility studies in male animals were not performed.
Scopolamine was one of the active ingredients in [[Asthmador]], an over the counter smoking preparation marketed in the 1950's and 60's claiming to combat [[asthma]] and [[bronchitis]].


Scopolamine was used in the [[1940]]s through the [[1960]]s that put mothers in labor into a kind of "[[twilight sleep]]" that didn’t stop pain, but merely eliminated the memory of pain by attacking the brain functions responsible for self-awareness and self-control. Often, this resulted in a kind of [[psychosis]], followed by [[post-traumatic stress]]-like memories in thousands of new mothers.<ref>''The Business of Being Born,'' [http://www.babystepsonline.net/BoBB.htm]</ref>
<!--Clinical Studies-->
|clinicalStudies=*Motion Sickness
:*In 195 adult subjects of different racial origins who participated in clinical efficacy studies at sea or in a controlled motion environment, there was a 75% reduction in the incidence of motion-induced [[nausea]] and [[vomiting]].


Scopolamine was an ingredient used in some over-the-counter sleep aids prior to November 1990 in the United States, when the FDA forced several hundred ingredients allegedly not known to be effective off the market.  Scopolamine shared a small segment of this market with [[diphenhydramine]], [[phenyltoloxamine]], [[pyrilamine]], [[doxylamine]] and other first generation [[antihistamines]], many of which are still used for this purpose in drugs like Sominex, [[Tylenol PM]], [[NyQuil]] and so on.
*Post-Operative Nausea and Vomiting
:*In two pivotal clinical efficacy studies in 391 adult female patients undergoing [[cesarean section]] or gynecological surgery with anesthesia and opiate analgesia, 66% of those treated with Transderm Scōp® (compared to only 46% of those receiving placebo) reported no retching/vomiting within the 24-hour period following administration of anesthesia/opiate analgesia. When the need for additional antiemetic medication was assessed during the same period, there was no need for medication in 76% of patients treated with Transderm Scōp® as compared to 59% of placebo-treated patients.


== Popular culture ==
<!--How Supplied-->
|howSupplied=* The Transderm Scōp® system is a tan-colored circular patch, 2.5 cm2, on a clear, oversized, hexagonal peel strip, which is removed prior to use.


* (1940) In one of crime fiction's all-time classic novels, ''[[Farewell, My Lovely]]'' (1940) by [[Raymond Chandler]], [[Philip Marlowe|Marlowe]] gets shot full of Scopolamine in a private sanitarium in order to both shut him up, and to pump him for knowledge, when he gets too close to the truth on a case, or rather several cases entangled into one another, that he is working on (the idenity of Velma and the whereabouts of Moose Malloy).
*Each Transderm Scōp® system contains 1.5 mg of scopolamine and is formulated to deliver in-vivo approximately 1 mg of scopolamine over 3 days. Transderm Scōp® is available in packages of 10 patches and 24 patches. Each patch is foil wrapped. Patient instructions are included.
:*1 Package (10 patches) NDC 10019-553-01
:*1 Package (24 patches) NDC 10019-553-02


<blockquote>
*Storage
"I had been shot full of dope to keep me quiet.  Perhaps scopolamine too, to make me talk." (quote by Marlowe in ''Farewell, My Lovely'')
:*The system should be stored at controlled room temperature between 20°C - 25°C (68°F - 77°F).
</blockquote>


<blockquote>
*Handling
"There's a drug called scopolamine, truth serum, that sometimes makes people talk without their knowing it. It's not sure fire, any more than hypnotism is. But it sometimes works." (quote by Marlowe in "Farewell, My Lovely")
:*Since scopolamine can cause temporary dilation of the pupils and blurred vision if it comes in contact with the eyes, patients should be strongly advised to wash their hands thoroughly with soap and water immediately after handling the patch. In addition, it is important that used patches be disposed of properly to avoid contact with children or pets.
</blockquote>


* (1957) In popular culture, scopolamine has achieved a moderate level of notoriety via its mention in the film ''[[I Was a Teenage Werewolf]]'', where Dr. Alfred Brandon uses it as part of his endeavor to regress the titular character to his "primitive roots."
<!--Patient Counseling Information-->
|fdaPatientInfo=*Transderm Scōp® Transdermal System


* (1961) Scopolamine is featured in the World War II action classic ''[[The Guns of Navarone (film)|The Guns of Navarone]]'' as a [[Schutzstaffel]] truth serum.
*Generic Name: scopolamine, pronounced skoe-POL-a-meen


* (1968) Scopolamine is featured in the World War II action classic ''[[Where Eagles Dare]]'' as a [[Schutzstaffel]] truth serum.
*Elderly patients should be informed that Transderm Scōp® may cause a greater likelihood of CNS effects, such as [[hallucinations]], confusion, [[dizziness]] and drug withdrawal syndrome and to seek immediate medical care if they become confused, disoriented or dizzy while wearing the patch or after removing.


* (1968) In [[Carlos Castaneda]]'s series of books ''The Teachings of Don Juan: A Yaqui Way of Knowledge'', the ''[[Datura]]'' plant is the favored shamanic, revelatory drug of the titular character.  The book explores, in depth, Castaneda's experiences under the influence of the drug, as well as the rites surrounding its use and preparation.  
*Patients should be informed that since Transderm Scōp® may cause [[drowsiness]], disorientation and confusion they should avoid engaging in activities that require mental alertness such as driving a motor vehicle or operating dangerous machinery.


* (1974) In episode 1 "That'll Be The Day", of the fourth series of the TV Series [[Callan (TV series)|Callan]], Callan is interrogated by the KGB using the drug Scopolamine as a truth serum.
*Patients who expect to participate in underwater sports should be cautioned regarding the potentially disorienting effects of Transderm Scōp®.


* (1979) Scopolamine is also mentioned several times in [[Robert Ludlum]]'s ''[[Matarese Dynasty]]'', a fictional spy novel in which the drug is known for its uses as a truth serum.
*Because of the possibility of drowsiness, disorientation and confusion, patients should be informed that they should avoid drinking alcohol. In addition, patients should be informed that the following medications should be used with caution when taking Transderm Scōp®:
:*sedatives or [[tranquilizers]]
:*drugs with [[anticholinergic]] properties (e.g., other belladonna alkaloids),
:*[[antihistamines]] (including [[meclizine]])
:*[[tricyclic antidepressants]]
:*[[muscle relaxants]]


* (1990) Scopolamine is mentioned by the villain Cain as one of the cutting agents of the drug Nuke in ''[[Robocop 2]]''
*Patients with the following conditions should be informed about the chance of developing serious reactions with Transderm Scōp®:
:*patients with [[open angle glaucoma]] (may cause an increase in [[intraocular pressure]])
:*patients with impaired kidney or liver function (increased likelihood of CNS effects)
:*patients with a history of [[seizures]] or psychosis (can potentially worsen both disorders)
:*patients with obstruction at the level of the pylorus, which is the outlet of the stomach, or urinary bladder neck obstruction (may cause difficulties in urinating)
:*patients suspected of having [[intestinal obstruction]]
:*pregnant or nursing mothers


* (1990s) The X-Files [[Red Museum]] shows Scopolamine as a suspect agent in usage for kidnappings.  
*Patients should be informed that if they remove the Transderm Scōp® patch suddenly before treatment is complete, the following withdrawal symptoms may occur: [[dizziness]], [[nausea]], [[vomiting]], [[abdominal cramps]], sweating, [[headache]], mental confusion, muscle weakness, slow [[heart rate]] and low blood pressure. Patients should be instructed to seek immediate medical care if they develop any of these symptoms after removing Transderm Scōp®.


* (2000) In the pilot episode for Season 1 of [[CSI: Crime Scene Investigation]], a female thief seduces a man to sleep with her. She applies scopolamine to her [[nipples]], which knocks the man out when he ingests it orally. After she robs him and makes her escape, the scopolamine which she absorbed into her skin causes her to pass out as well.
*Patients should be informed that Transderm Scōp® can cause temporary dilation of the pupils and blurred vision if it comes in contact with the eyes. Patients should be informed to wash their hands thoroughly with soap and water immediately after handling the patch. In addition, patients should be informed that used patches must be disposed of properly to avoid contact with children or pets.


* (2000) Scopolamine was the drug Michael claimed he was injected with either by the military and/or the aliens in "[http://www.metatech.org/TheMarsRecords.pdf The Mars Records]". It might be worth noting in this context that scopolamine can cause [[confabulation]] (the mixing of memory and facts).
*Patients should be informed that skin burns have been reported at the patch site in several patients wearing an aluminized transdermal system during a Magnetic Resonance Imaging scan (MRI). Because Transderm Scōp® contains aluminum, patients should be advised to remove the system before undergoing an MRI.


* (2007) In the episode "[[Airborne (House episode)|Airborne]]", one character in the TV show ''[[House (TV series)|House, M.D.]]'' is shown wearing a scopolamine patch.
*Patients should be advised to use only one patch at a time.


== External links ==
*Patients should be advised not to cut the patch.
* [http://www.erowid.org/chemicals/scopolamine/scopolamine.shtml The Erowid Scopolamine Vault]
* [http://www.transdermscop.com/infomed_prescribing.htm Scopolamine Transdermal Patch Information:]
* [http://www.sobercircle.com/index.asp?node=resources&section=articles&fileid=8 Sober Circle Article on Dangers of Scopolamine]


== References ==
: [[File:Scopolamine03.png|thumb|none|400px|This image is provided by the National Library of Medicine.]]
{{reflist}}


{{ancient anaesthesia-footer}}
<!--Precautions with Alcohol-->
{{Antiemetics and antinauseants}}
|alcohol=* Alcohol-Scopolamine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
{{Hypnotics and sedatives}}
{{Mydriatics and cycloplegics}}
{{Deliriants}}


[[Category:Natural tropane alkaloids]]
<!--Brand Names-->
[[Category:Deliriants]]
|brandNames=* TRANSDERM SCOP®<ref>{{Cite web | title = TRANSDERM SCOP  scopalamine patch, extended release | url = http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8e5dab9c-755b-460e-afe2-1ddfc4acfd96 }}</ref>
[[Category:Muscarinic antagonists]]
[[Category:Epoxides]]


[[Category:Plant toxins]]
<!--Look-Alike Drug Names-->
|lookAlike=<!--Drug Shortage Status-->
|drugShortage=
}}
{{PillImage
|fileName=No image.jpg
}}
{{LabelImage
|fileName=Scopolamine04.png
}}
{{LabelImage
|fileName=Scopolamine05.png
}}
{{LabelImage
|fileName=Scopolamine06.png
}}
<!--Pill Image-->


<!--Label Display Image-->


[[cs:Skopolamin]]
<!--Category-->
[[de:Scopolamin]]
[[es:Escopolamina]]
[[fr:Scopolamine]]
[[it:Scopolamina]]
[[lt:Skopolaminas]]
[[hu:Szkopolamin]]
[[nl:Scopolamine]]
[[ja:スコポラミン]]
[[pl:Skopolamina]]
[[pt:Escopolamina]]
[[ro:Scopolamină]]
[[ru:Скополамин]]
[[sk:Skopolamín]]
[[sv:Skopolamin]]
[[tr:Skopolamin]]


{{jb1}}
[[Category:Drug]]
{{WH}}
[[Category:Anticholinergics]]
{{WS}}
[[Category:Muscarinic antagonists]]

Latest revision as of 13:46, 8 May 2015

Scopolamine (transdermal)
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Vignesh Ponnusamy, M.B.B.S. [2]

Disclaimer

WikiDoc MAKES NO GUARANTEE OF VALIDITY. WikiDoc is not a professional health care provider, nor is it a suitable replacement for a licensed healthcare provider. WikiDoc is intended to be an educational tool, not a tool for any form of healthcare delivery. The educational content on WikiDoc drug pages is based upon the FDA package insert, National Library of Medicine content and practice guidelines / consensus statements. WikiDoc does not promote the administration of any medication or device that is not consistent with its labeling. Please read our full disclaimer here.

Overview

Scopolamine (transdermal) is an anticholinergic agent that is FDA approved for the treatment of motion sickness, post operative nausea and vomiting. Common adverse reactions include dry mouth, dizziness, somnolence, urinary retention, agitation, visual impairment, confusion, mydriasis and pharyngitis.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Motion Sickness
  • Initiation of Therapy
  • To prevent the nausea and vomiting associated with motion sickness, one Transderm Scōp® patch (formulated to deliver approximately 1mg of scopolamine over 3 days) should be applied to the hairless area behind one ear at least 4 hours before the antiemetic effect is required.
  • Continuation of Therapy
  • If therapy is required for longer than 3 days, the first patch should be removed and a fresh one placed on the hairless area behind the other ear.
Post Operative Nausea and Vomiting
  • Initiation of Therapy
  • To prevent post operative nausea and vomiting, one Transderm Scōp® patch should be applied the evening before scheduled surgery, except for caesarian section.
  • For caesarian section surgery, to minimize exposure of the newborn baby to the drug, apply the patch one hour prior to caesarian section
  • Continuation of Therapy
  • For perioperative use, the patch should be kept in place for 24 hours following surgery at which time it should be removed and discarded.

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Scopolamine in adult patients.

Non–Guideline-Supported Use

Excessive salivation; Prophylaxis
  • Dosing Information
  • Transdermal scopolamine reduced salivation.[1]

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

There is limited information regarding FDA-Labeled Use of Scopolamine in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Scopolamine in pediatric patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Scopolamine in pediatric patients.

Contraindications

  • Persons who are hypersensitive to the drug scopolamine or other belladonna alkaloids or to any ingredient or component in the formulation or delivery system.

Warnings

Precautions

  • Open Angle Glaucoma
  • Patients currently being treated for Open Angle Glaucoma
  • Glaucoma therapy in patients with open angle glaucoma should be monitored and may need to be adjusted during Transderm Scōp® use, as the mydriatic effect of scopolamine may cause an increase in intraocular pressure.
  • Patients should be advised to remove the patch immediately and promptly contact a physician in the event that they experience symptoms of acute angle closure glaucoma (pain and reddening of the eyes, accompanied by dilated pupils).
  • Temporary Dilation of the Pupil
  • Scopolamine can cause temporary dilation of the pupils and blurred vision if it comes in contact with the eyes.
  • Patients should be strongly advised to wash their hands thoroughly with soap and water immediately after handling the patch. In addition, it is important that used patches be disposed of properly to avoid contact with children or pets.
  • Preexisting Gastrointestinal or Urinary Bladder Obstructions
  • Transderm Scōp® should be used with caution in patients with pyloric obstruction or urinary bladder neck obstruction. Caution should be exercised when administering an antiemetic or anticholinergic drug, including Transderm Scōp®, to patients suspected of having intestinal obstruction.
  • Patients should be instructed to remove the patch if they develop any difficulties in urinating.
  • History of Seizures or Psychosis
  • Transderm Scōp® should be used with caution in patients with a history of seizures or psychosis since scopolamine can potentially aggravate both disorders.
  • Idiosyncratic Reactions
  • Specific Populations
  • Pediatric
  • A safe and effective dose has not been established in the pediatric population. Children are particularly susceptible to the side effects of belladonna alkaloids; including mydriasis, hallucinations, amyblyopia, and drug withdrawal syndrome. Neurologic and psychiatric adverse reactions, such as hallucinations, amblyopia and mydriasis have also been reported when one half or one quarter of a patch has been applied.
  • Elderly
  • Transderm Scōp® should be used with caution in the elderly because of the increased likelihood of CNS effects, such as hallucinations, confusion, dizziness and drug withdrawal syndrome. Clinical trials of Transderm Scōp® did not include sufficient number of subjects aged 65 years and older to determine if they respond differently from younger subjects.
  • Renal and Hepatic Impaired
  • Transderm Scōp® should be used with caution in individuals with impaired renal or hepatic functions because of the increased likelihood of CNS effects. Transderm Scōp® has not been studied in these populations.
  • Safety Hazards
  • Drowsiness
  • Since drowsiness, disorientation, and confusion may occur with the use of scopolamine, patients should be warned of the possibility and cautioned against engaging in activities that require mental alertness, such as driving a motor vehicle or operating dangerous machinery.
  • Disorienting Effects
  • Patients who expect to participate in underwater sports should be cautioned regarding the potentially disorienting effects of scopolamine.
  • MRI Skin Burns
  • Skin burns have been reported at the patch site in several patients wearing an aluminized transdermal system during a Magnetic Resonance Imaging scan (MRI). Because Transderm Scōp® contains aluminum, it is recommended to remove the system before undergoing an MRI.

Adverse Reactions

Clinical Trials Experience

  • Because clinical trials are conducted under widely varying conditions, adverse reaction rates observed in the clinical trials of a drug cannot be directly compared to rates in the clinical trials of another drug and may not reflect the rates observed in clinical practice.
Motion Sickness
  • In motion sickness clinical studies of Transderm Scōp®, the most frequent adverse reaction was dry mouth. This occurred in about two thirds of patients on drug. A less frequent adverse drug reaction was drowsiness, which occurred in less than one sixth of patients on drug. Transient impairment of eye accommodation, including blurred vision and dilation of the pupils, was also observed.
Post-Operative Nausea and Vomiting
  • In a total of five clinical studies in which Transderm Scōp® was administered perioperatively to a total of 461 patients where safety was assessed, dry mouth was the most frequently reported adverse drug reaction, which occurred in approximately 29% of patients on drug. Dizziness was reported by approximately 12% of patients on drug. Other adverse drug reactions reported from these studies, with a frequency of ≥3% of patients treated with Transderm Scop and with a frequency higher than placebo were, in descending order: somnolence, urinary retention, agitation/restlessness, visual impairment, confusion, mydriasis and pharyngitis (see Table 6.1).
This image is provided by the National Library of Medicine.

Postmarketing Experience

  • The following adverse drug reactions, further to those reported from clinical trials, have been identified during postapproval use of Transderm Scōp®. Because these reactions are reported voluntarily from a population of uncertain size, it is not always possible to reliably estimate their frequency or to confirm a definite causal relationship.
  • In worldwide marketing with Transderm Scōp®, the following adverse drug reactions were reported by body system.
Psychiatric disorders

Acute psychosis including: hallucinations disorientation, and paranoia.

Nervous system disorders

Headache, amnesia, coordination abnormalities, speech disorder, disturbance in attention, restlessness.

General disorders and administration site conditions

Burning sensation in the application site.

Eye disorders

Dry eyes, eye pruritis, angle closure glaucoma, amblyopia, eyelid irritation.

Skin and subcutaneous tissue disorders

Generalized rash, skin irritation, erythema.

Renal and urinary disorders

Dysuria.

Ear and Labyrinth Disorders

Vertigo.

Drug Interactions

  • The absorption of oral medications may be decreased during the concurrent use of scopolamine because of decreased gastric motility and delayed gastric emptying.
  • Scopolamine should be used with caution in patients taking other drugs that are capable of causing CNS effects such as sedatives, tranquilizers, or alcohol. Special attention should be paid to potential interactions with drugs having anticholinergic properties; e.g., other belladonna alkaloids, antihistamines (including meclizine), tricyclic antidepressants, and muscle relaxants.
  • In vitro studies indicated that the potential for scopolamine to alter the pharmacokinetics of other concomitant medications through inhibition of CYP 1A2, 2C8, 2C9, 2C19, 2D6 and 3A4 or induction of CYP 1A2 and 3A4 is low; however, in vivo studies have not been conducted.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category C
  • Based on data from one prospective study of Transderm Scōp® in cesarean delivery, the rate of newborn adverse events in both the Transderm Scōp® and placebo groups were the same. The rates were 10.5% (12 events in 114 newborns) in both treatment groups. None of these events were considered life threatening or drug related. Jaundice was the only adverse event occurring more frequently with Transderm Scōp® than placebo: 9 events (7.9%) versus 2 events (1.8%) (p=0.031). Jaundice, a common occurrence in newborns, resolved with ultraviolet light and did not prolong the hospital stay.
  • There are no adequate and well-controlled studies of Transderm Scōp® use during pregnancy. In animal reproduction studies, when pregnant rats and rabbits received scopolamine hydrobromide by daily intravenous injection, no adverse effects were observed in rats. An embryotoxic effect was observed in rabbits at doses producing plasma levels approximately 100 times the levels achieved in humans using a transdermal system. Transderm Scōp® should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus and the mother.


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Scopolamine in women who are pregnant.

Labor and Delivery

  • During a clinical study among women undergoing cesarean section treated with Transderm Scōp® in conjunction with epidural anesthesia and opiate analgesia, no evidence of CNS depression was found in newborns. Scopolamine administered parenterally to rats and rabbits at doses higher than the dose delivered by Transderm Scōp® did not affect uterine contractions or increase the duration of labor. Scopolamine does cross the placenta.

Nursing Mothers

  • Scopolamine is excreted in human milk. Caution should be exercised when Transderm Scōp® is administered to a nursing woman.

Pediatric Use

  • A safe and effective dose has not been established in the pediatric population.

Geriatic Use

  • Transderm Scōp® should be used with caution in the elderly because of the increased likelihood of CNS effects, such as hallucinations, confusion and dizziness. Clinical trials of Transderm Scōp® did not include sufficient number of subjects aged 65 years and older to determine if they respond differently from younger subjects.

Gender

There is no FDA guidance on the use of Scopolamine with respect to specific gender populations.

Race

There is no FDA guidance on the use of Scopolamine with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Scopolamine in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Scopolamine in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Scopolamine in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Scopolamine in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Transdermal

Monitoring

There is limited information regarding Monitoring of Scopolamine in the drug label.

IV Compatibility

There is limited information regarding IV Compatibility of Scopolamine in the drug label.

Overdosage

Acute Overdose

Signs and Symptoms

  • The symptoms of overdose/toxicity due to scopolamine should be carefully distinguished from the occasionally observed syndrome of withdrawal. Although mental confusion and dizziness may be observed with both acute toxicity and withdrawal, other characteristic findings differ: tachyarrhythmias, dry skin, and decreased bowel sounds suggest anticholinergic toxicity, while bradycardia, headache, nausea and abdominal cramps, and sweating suggest post-removal withdrawal. Obtaining a careful history is crucial to making the correct diagnosis.

Management

  • Because strategies for the management of drug overdose continually evolve, it is strongly recommended that a poison control center be contacted to obtain up-to-date information regarding the management of Transderm Scōp® patch overdose. The prescriber should be mindful that antidotes used routinely in the past may no longer be considered optimal treatment. For example, physostigmine, used more or less routinely in the past, is seldom recommended for the routine management of anticholinergic syndromes.
  • Until up-to-date authoritative advice is obtained, routine supportive measures should be directed to maintaining adequate respiratory and cardiac function.
  • In cases of toxicity remove the patch. Serious symptomatic cases of overdosage involving multiple patch applications and/or ingestion may be managed by initially ensuring the patient has an adequate airway, and supporting respiration and circulation. This should be rapidly followed by removal of all patches from the skin and the mouth. If there is evidence of patch ingestion, gastric lavage, endoscopic removal of swallowed patches, or administration of activated charcoal should be considered, as indicated by the clinical situation. In any case where there is serious overdosage or signs of evolving acute toxicity, continuous monitoring of vital signs and ECG, establishment of intravenous access, and administration of oxygen are all recommended.

Chronic Overdose

There is limited information regarding Chronic Overdose of Scopolamine in the drug label.

Pharmacology

Template:Px
Template:Px
Scopolamine (transdermal)
Systematic (IUPAC) name
(–)-(S)-3-Hydroxy-2-phenylpropionic acid (1R,2R,4S,7S,9S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester
Identifiers
CAS number 51-34-3
ATC code A04AD01 N05CM05 (WHO), S01FA02 (WHO)
PubChem 5184
DrugBank DB00747
Chemical data
Formula Template:OrganicBox atomTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox 
Mol. mass 303.353 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 0.13-8% (Oral)
Metabolism Hepatic (liver)
Half life 4.5 hours[2]
Excretion Renal
Therapeutic considerations
Pregnancy cat.

B2(AU) C(US)

Legal status

Prescription Only (S4)(AU) ?(CA) POM(UK) [[Prescription drug|Template:Unicode-only]](US)

Routes transdermal, ocular, oral, subcutaneous, intravenous, sublingual, rectal, buccal transmucousal, intramuscular

Mechanism of Action

  • Scopolamine, a belladonna alkaloid, is an anticholinergic agent. Scopolamine acts: i) as a competitive inhibitor at postganglionic muscarinic receptor sites of the parasympathetic nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the central nervous system (CNS) by blocking cholinergic transmission from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center. Scopolamine can inhibit the secretion of saliva and sweat, decrease gastrointestinal secretions and motility, cause drowsiness, dilate the pupils, increase heart rate, and depress motor function.

Structure

  • The Transderm Scōp® (scopolamine) transdermal system is a circular flat patch designed for continuous release of scopolamine following application to an area of intact skin on the head, behind the ear. Each system contains 1.5 mg of scopolamine base. Scopolamine is α -(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.02,4] non-7-yl ester. The empirical formula is C17H21NO4 and its structural formula is:
This image is provided by the National Library of Medicine.
  • Scopolamine is a viscous liquid that has a molecular weight of 303.35 and a pKa of 7.55-7.81. The Transderm Scōp® system is a film 0.2 mm thick and 2.5 cm2, with four layers. Proceeding from the visible surface towards the surface attached to the skin, these layers are: (1) a backing layer of tan-colored, aluminized, polyester film; (2) a drug reservoir of scopolamine, light mineral oil, and polyisobutylene; (3) a microporous polypropylene membrane that controls the rate of delivery of scopolamine from the system to the skin surface; and (4) an adhesive formulation of mineral oil, polyisobutylene, and scopolamine. A protective peel strip of siliconized polyester, which covers the adhesive layer, is removed before the system is used. The inactive components, light mineral oil (12.4 mg) and polyisobutylene (11.4 mg), are not released from the system.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Scopolamine in the drug label.

Pharmacokinetics

  • The pharmacokinetics of scopolamine delivered via the system are due to the characteristics of both the drug and dosage form. The system is formulated to deliver in-vivo approximately 1 mg of scopolamine at an approximately constant rate to the systemic circulation over 3 days. Upon application to the postauricular skin, an initial priming dose of scopolamine is released from the adhesive layer to saturate skin-binding sites. The subsequent delivery of scopolamine to the blood is determined by the rate controlling membrane and is designed to produce stable plasma levels in a therapeutic range. Following removal of the used system, there is some degree of continued systemic absorption of scopolamine bound in the skin layers.
  • Absorption
  • Scopolamine is well absorbed percutaneously. Following application to the skin behind the ear, circulating plasma levels are detected within 4 hours with peak levels being obtained, on average, within 24 hours. The average plasma concentration produced is 87 pg/mL (0.28 nM) for free scopolamine and 354 pg/mL for total scopolamine (free + conjugates).
  • Distribution
  • The distribution of scopolamine is not well characterized. It crosses the placenta and the blood brain barrier and may be reversibly bound to plasma proteins.
  • Metabolism and Excretion
  • The exact elimination pattern of scopolamine has not been determined. Following patch removal, plasma levels of scopolamine decline in a log linear fashion with an observed half-life of 9.5 hours. Less than 10% of the total dose is excreted in the urine as the parent drug and metabolites over 108 hours. Scopolamine is extensively metabolized and conjugated with less than 5% of the total dose appearing unchanged in the urine. The enzymes responsible for metabolizing scopolamine are unknown.
  • Drug Interaction
  • An in vitro study using human hepatocytes examined the induction of CYP1A2 and CYP3A4 by scopolamine. Scopolamine did not induce CYP1A2 and CYP3A4 isoenzymes at the concentrations up to 10 nM. In an in vitro study using human liver microsomes which evaluated the inhibition of CYP1A2, 2C8, 2C9, 2C19, 2D6 and 3A4, scopolamine did not inhibit these cytochrome P450 isoenzymes at the concentrations up to 1 mcM.

Nonclinical Toxicology

  • No long-term studies in animals have been conducted to evaluate the carcinogenic potential of scopolamine. The mutagenic potential of scopolamine has not been evaluated.
  • Fertility studies were performed in female rats and revealed no evidence of impaired fertility or harm to the fetus due to scopolamine hydrobromide administered by daily subcutaneous injection. Maternal body weights were reduced in the highest-dose group (plasma level approximately 500 times the level achieved in humans using a transdermal system). However, fertility studies in male animals were not performed.

Clinical Studies

  • Motion Sickness
  • In 195 adult subjects of different racial origins who participated in clinical efficacy studies at sea or in a controlled motion environment, there was a 75% reduction in the incidence of motion-induced nausea and vomiting.
  • Post-Operative Nausea and Vomiting
  • In two pivotal clinical efficacy studies in 391 adult female patients undergoing cesarean section or gynecological surgery with anesthesia and opiate analgesia, 66% of those treated with Transderm Scōp® (compared to only 46% of those receiving placebo) reported no retching/vomiting within the 24-hour period following administration of anesthesia/opiate analgesia. When the need for additional antiemetic medication was assessed during the same period, there was no need for medication in 76% of patients treated with Transderm Scōp® as compared to 59% of placebo-treated patients.

How Supplied

  • The Transderm Scōp® system is a tan-colored circular patch, 2.5 cm2, on a clear, oversized, hexagonal peel strip, which is removed prior to use.
  • Each Transderm Scōp® system contains 1.5 mg of scopolamine and is formulated to deliver in-vivo approximately 1 mg of scopolamine over 3 days. Transderm Scōp® is available in packages of 10 patches and 24 patches. Each patch is foil wrapped. Patient instructions are included.
  • 1 Package (10 patches) NDC 10019-553-01
  • 1 Package (24 patches) NDC 10019-553-02
  • Storage
  • The system should be stored at controlled room temperature between 20°C - 25°C (68°F - 77°F).
  • Handling
  • Since scopolamine can cause temporary dilation of the pupils and blurred vision if it comes in contact with the eyes, patients should be strongly advised to wash their hands thoroughly with soap and water immediately after handling the patch. In addition, it is important that used patches be disposed of properly to avoid contact with children or pets.

Storage

There is limited information regarding Scopolamine (transdermal) Storage in the drug label.

Images

Drug Images

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Package and Label Display Panel

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Patient Counseling Information

  • Transderm Scōp® Transdermal System
  • Generic Name: scopolamine, pronounced skoe-POL-a-meen
  • Elderly patients should be informed that Transderm Scōp® may cause a greater likelihood of CNS effects, such as hallucinations, confusion, dizziness and drug withdrawal syndrome and to seek immediate medical care if they become confused, disoriented or dizzy while wearing the patch or after removing.
  • Patients should be informed that since Transderm Scōp® may cause drowsiness, disorientation and confusion they should avoid engaging in activities that require mental alertness such as driving a motor vehicle or operating dangerous machinery.
  • Patients who expect to participate in underwater sports should be cautioned regarding the potentially disorienting effects of Transderm Scōp®.
  • Because of the possibility of drowsiness, disorientation and confusion, patients should be informed that they should avoid drinking alcohol. In addition, patients should be informed that the following medications should be used with caution when taking Transderm Scōp®:
  • Patients with the following conditions should be informed about the chance of developing serious reactions with Transderm Scōp®:
  • patients with open angle glaucoma (may cause an increase in intraocular pressure)
  • patients with impaired kidney or liver function (increased likelihood of CNS effects)
  • patients with a history of seizures or psychosis (can potentially worsen both disorders)
  • patients with obstruction at the level of the pylorus, which is the outlet of the stomach, or urinary bladder neck obstruction (may cause difficulties in urinating)
  • patients suspected of having intestinal obstruction
  • pregnant or nursing mothers
  • Patients should be informed that if they remove the Transderm Scōp® patch suddenly before treatment is complete, the following withdrawal symptoms may occur: dizziness, nausea, vomiting, abdominal cramps, sweating, headache, mental confusion, muscle weakness, slow heart rate and low blood pressure. Patients should be instructed to seek immediate medical care if they develop any of these symptoms after removing Transderm Scōp®.
  • Patients should be informed that Transderm Scōp® can cause temporary dilation of the pupils and blurred vision if it comes in contact with the eyes. Patients should be informed to wash their hands thoroughly with soap and water immediately after handling the patch. In addition, patients should be informed that used patches must be disposed of properly to avoid contact with children or pets.
  • Patients should be informed that skin burns have been reported at the patch site in several patients wearing an aluminized transdermal system during a Magnetic Resonance Imaging scan (MRI). Because Transderm Scōp® contains aluminum, patients should be advised to remove the system before undergoing an MRI.
  • Patients should be advised to use only one patch at a time.
  • Patients should be advised not to cut the patch.
This image is provided by the National Library of Medicine.

Precautions with Alcohol

  • Alcohol-Scopolamine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

  • TRANSDERM SCOP®[3]

Look-Alike Drug Names

There is limited information regarding Scopolamine (transdermal) Look-Alike Drug Names in the drug label.

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Talmi YP, Finkelstein Y, Zohar Y (1990). "Reduction of salivary flow with transdermal scopolamine: a four-year experience". Otolaryngol Head Neck Surg. 103 (4): 615–8. PMID 2123321.
  2. ↑ Putcha, L.; Cintrón, N. M.; Tsui, J.; Vanderploeg, J. M.; Kramer, W. G. (1989). "Pharmacokinetics and Oral Bioavailability of Scopolamine in Normal Subjects". Pharmacology Research. 6 (6): 481–485. doi:10.1023/A:1015916423156. PMID 2762223.
  3. ↑ "TRANSDERM SCOP scopalamine patch, extended release".

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