View source for Salicylic acid

{{DrugProjectFormSinglePage
|authorTag={{Ammu}}
|genericName=Salicylic acid
|aOrAn=a
|drugClass=anti [[acne]] agent
|indicationType=treatment
|indication=[[acne]], for relief of [[itching]], irritation, [[redness]] and scaling assoicated with [[psoriasis]], [[eczema]] and [[seborrheic dermatitis]]
|adverseReactions=[[hypersensitivity]] reaction, salicylate toxicity
|blackBoxWarningTitle=<span style="color:#FF0000;">ConditionName: </span>
|blackBoxWarningBody=<i><span style="color:#FF0000;">ConditionName: </span></i>

* Content

<!--Adult Indications and Dosage-->

<!--FDA-Labeled Indications and Dosage (Adult)-->
|fdaLIADAdult=* FOR THE TREATMENT OF ACNE
* HELPS KEEP SKIN CLEAR OF NEW ACNE BLEMISHES
* For relief of itching, irritation, redness and scaling assoicated with [[psoriasis]], [[eczema]] and [[seborrheic dermatitis]].
|offLabelAdultGuideSupport=* [[Acne vulgaris]]
:* Apply TOPICALLY in concentrations of 0.5% to 10%
:* Disorder of skin, Hyperkeratotic: gel, apply TOPICALLY to the affected area and occlude the area at night.
* Disorder of skin, Hyperkeratotic
:* shampoo, wet hair and apply TOPICALLY to the scalp, work into a lather and rinse; repeat the treatment as needed until the condition clears [5]
* Psoriasis
:* Apply TOPICALLY in concentrations of 3% to 6%
* Removal of wart
:* Apply TOPICALLY once or twice daily in concentrations of 5% to 40% for up to 12 weeks
|offLabelAdultNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.

<!--Pediatric Indications and Dosage-->

<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed=There is limited information regarding <i>FDA-labeled indications and dosage information</i> of {{PAGENAME}} in pediatric patients.
|offLabelPedGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.

<!--Non–Guideline-Supported Use (Pediatric)-->
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.

<!--Contraindications-->
|warnings=* For external use only.
* Avoid contact with eyes. If contact occurs, rinse thoroughly with water.
* Do not use without consulting a doctor if the condition appears over a large portion of hte body.
* If condition worsens, or does not improve after using as directed, consult physician.
* Do not use for prolonged periods without consulting a doctor.
|clinicalTrials=There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
|postmarketing=There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
|useInPregnancyFDA=* '''Pregnancy Category'''
|useInPregnancyAUS=* '''Australian Drug Evaluation Committee (ADEC) Pregnancy Category'''

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of {{PAGENAME}} in women who are pregnant.
|useInLaborDelivery=There is no FDA guidance on use of {{PAGENAME}} during labor and delivery.
|useInNursing=There is no FDA guidance on the use of {{PAGENAME}} with respect to nursing mothers.
|useInPed=There is no FDA guidance on the use of {{PAGENAME}} with respect to pediatric patients.
|useInGeri=There is no FDA guidance on the use of {{PAGENAME}} with respect to geriatric patients.
|useInGender=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific gender populations.
|useInRace=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific racial populations.
|useInRenalImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with renal impairment.
|useInHepaticImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with hepatic impairment.
|useInReproPotential=There is no FDA guidance on the use of {{PAGENAME}} in women of reproductive potentials and males.
|useInImmunocomp=There is no FDA guidance one the use of {{PAGENAME}} in patients who are immunocompromised.

<!--Administration and Monitoring-->
|administration=* Topical
|monitoring=There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.


<!--IV Compatibility-->
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.

<!--Overdosage-->
|overdose=There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.

<!--Pharmacology-->

<!--Drug box 2-->
|drugBox={{chembox2
| Watchedfields = changed
| verifiedrevid = 477314005
| Name = Salicylic acid
| ImageFileL1 = Salicylic-acid-skeletal.svg
| ImageSizeL1 = 100px
| ImageNameL1 = Skeletal formula of salicylic acid
| ImageFileR1 = Salicylic-acid-from-xtal-2006-3D-balls.png
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model of salicylic acid
| ImageFile2 = Kwas salicylowy.jpg
| ImageSize2 = 200px
| ImageName2 = Salicylic acid
| IUPACName = 2-Hydroxybenzoic acid
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O414PZ4LPZ
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00097
| InChI = 1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
| InChIKey = YGSDEFSMJLZEOE-UHFFFAOYAQ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 424
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YGSDEFSMJLZEOE-UHFFFAOYSA-N
| CASNo = 69-72-7
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 338
| EINECS = 200-712-3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 331
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00936
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16914
| SMILES = c1ccc(c(c1)C(=O)O)O
| ATCCode_prefix = A01
| ATCCode_suffix = AD05
| ATC_Supplemental = {{ATC|B01|AC06}} {{ATC|D01|AE12}} {{ATC|N02|BA01}} {{ATC|S01|BC08}}
| RTECS = VO0525000
}}
| Section2 = {{Chembox Properties
| C=7|H=6|O=3
| Appearance = colorless to white crystals
| Odor = odorless
| MeltingPtC = 158.6
| BoilingPtC = 200
| Boiling_notes = <br> decomposes<ref name=chemister /><br> {{convert|211|C|F K}}<br> at 20 mmHg<ref name=crc>{{RubberBible92nd|page=3.306}}</ref>
| pKa = 1 = 2.97 (25 °C)<ref>[http://www.drugbank.ca/drugs/DB00936 Salicyclic acid]. Drugbank.ca. Retrieved on 2012-06-03.</ref><br> 2 = 13.82 (20 °C)<ref name=chemister />
| Density = 1.443 g/cm<sup>3</sup> (20 °C)<ref name=crc/>
| Solubility = 1.24 g/L (0 °C)<br> 2.48 g/L (25 °C)<br> 4.14 g/L (40 °C)<br> 17.41 g/L (75 °C)<ref name=chemister>http://chemister.ru/Database/properties-en.php?dbid=1&id=1777</ref><br> 77.79 g/L (100 °C)<ref name=sioc>{{cite book|last = Seidell|first = Atherton|last2 = Linke|first2 = William F.|year = 1952|title = Solubilities of Inorganic and Organic Compounds|publisher = Van Nostrand|url = [http://books.google.com/books?id=k2e5AAAAIAAJ Google Books]|accessdate = 2014-05-29}}</ref>
| SolubleOther = soluble in [[ether]], [[carbon tetrachloride|CCl<sub>4</sub>]], [[benzene]], [[propanol]], [[acetone]], [[ethanol]], [[oil of turpentine]], [[toluene]]
| Solubility1 = 0.46 g/100 g (11.7 °C)<br> 0.775 g/100 g (25 °C)<br> 0.991 g/100 g (30.5 °C)<br> 2.38 g/100 g (49.4 °C)<br> 4.4 g/100 g (64.2 °C)<ref name=chemister /><ref name=sioc />
| Solvent1 = benzene
| Solubility2 = 2.22 g/100 mL (25 °C)<ref name=sioc /><br> 2.31 g/100 mL (30.5 °C)<ref name=chemister />
| Solvent2 = chloroform
| Solubility3 = 40.67 g/100 g (−3 °C)<br> 62.48 g/100 g (21 °C)<ref name=chemister />
| Solvent3 = methanol
| Solubility4 = 2.43 g/100 g (23 °C)<ref name=chemister />
| Solvent4 = olive oil
| Solubility5 = 39.6 g/100 g (23 °C)<ref name=chemister />
| Solvent5 = acetone
| RefractIndex = 1.565 (20 °C)<ref name=crc/>
| LogP = 2.26
| VaporPressure = 10.93 mPa<ref name=pubchem>{{PubChemLink|338}}</ref>
| SublimationConditions = sublimes at 76 °C<ref name=pubchem />
| LambdaMax = 210 nm, 234 nm, 303 nm (4&nbsp;mg % in ethanol)<ref name=pubchem />
 }}
| Section5 = {{Chembox Thermochemistry
| DeltaHf = -589.9 kJ/mol
| DeltaHc = 3.025 MJ/mol<ref name=NIST>http://webbook.nist.gov/cgi/cbook.cgi?ID=C69727&Type=HCOMBS</ref>
 }}
| Section8 = {{Chembox Related
| OtherCpds = [[Methyl salicylate]],<br />[[Benzoic acid]],<br />[[Phenol]], [[Aspirin]],<br />[[4-Hydroxybenzoic acid]],<br /> [[Magnesium salicylate]],<br />[[Choline salicylate]],<br />[[Bismuth subsalicylate]],<br />[[Sulfosalicylic acid]]
 }}
| Section6 = {{Chembox Hazards
| ExternalMSDS = [http://avogadro.chem.iastate.edu/MSDS/salicylic_acid.htm MSDS]
| GHSPictograms = {{GHS05}}{{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=w398500|name=Salicylic acid|accessdate=2014-05-23}}</ref>
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|318}}<ref name="sigma" />
| PPhrases = {{P-phrases|280|305+351+338}}<ref name="sigma" />
| RPhrases = {{R22}}, {{R38}}, {{R41}}, {{R61}}
| SPhrases = {{S22}}, {{S26}}, {{S36}}, {{S37}}, {{S39}}
| EUClass = {{Hazchem Xn}}
| EUIndex = 200-712-3
| MainHazards =
| SkinHazard = Mild irritation
| EyeHazard = Severe irritation
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| FlashPtC = 157
| Flash_notes = <br> closed cup<ref name=pubchem />
| AutoignitionPtC = 540
| Autoignition_ref = <ref name=pubchem />
| ExploLimits =
| PEL =
| LD50 = 480 mg/kg (mice, oral)
 }}
}}
|mechAction=* Salicylic acid has been shown to work through several different pathways. It produces its anti-inflammatory effects via suppressing the activity of cyclooxygenase (COX), an enzyme that is responsible for the production of pro-inflammatory mediators such as the prostaglandins. 
* It does this not by direct inhibition of COX like most other non-steroidal anti-inflammatory drugs (NSAIDs) but instead by suppression of the expression of the enzyme (via a yet-unelucidated mechanism).<ref name=American chemical society>{{cite web | title = American chemical society | url =http://www.cas.org/news/insights/science-connections/aspirin}}</ref>
* Salicylic acid has also been shown to activate adenosine monophosphate-activated protein kinase (AMPK), and it is thought that this action may play a role in the anticancer effects of the compound and its prodrugs aspirin and salsalate. In addition, the antidiabetic effects of salicylic acid are likely mediated by AMPK activation primarily through allosteric conformational change that increases levels of phosphorylation.<ref name="pmidPMID 22517326">{{cite journal| author=Hawley SA, Fullerton MD, Ross FA, Schertzer JD, Chevtzoff C, Walker KJ et al.| title=The ancient drug salicylate directly activates AMP-activated protein kinase. | journal=Science | year= 2012 | volume= 336 | issue= 6083 | pages= 918-22 | pmid=PMID 22517326 | doi=10.1126/science.1215327 | pmc=PMC3399766 | url=http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=22517326  }} </ref>
* Salicylic acid also uncouples oxidative phosphorylation, which leads to increased ADP:ATP and AMP:ATP ratios in the cell. As a consequence, salicylic acid may alter AMPK activity and subsequently exert its anti-diabetic properties through altered energy status of the cell. Even in AMPK knock-out mice, however, there is an anti-diabetic effect, demonstrating that there is at least one additional, yet-unidentified action of the compound.
<ref name=Newscientist>{{cite web | title = Newscientist | url =http://www.newscientist.com/article/dn21718-clues-to-aspirins-anticancer-effects-revealed.html }}</ref>
|structure=<!--Pharmacodynamics-->
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.

<!--Pharmacokinetics-->
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.

<!--Nonclinical Toxicology-->
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.

<!--Clinical Studies-->
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.

<!--How Supplied-->
|howSupplied=<!--Patient Counseling Information-->
|fdaPatientInfo=* Wash affected areas well with soap and water. Pat dry. Apply cream to affected area one to four times per day, or as directed by physician.
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

<!--Brand Names-->
|brandNames=* ALA-SEPTIC®<ref>{{Cite web | title =ALA-SEPTIC- salicylic acid cream   | url =http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=edb70750-bea8-4c0f-9453-f2c38d2f05d9  }}</ref>
|drugShortage=
}}
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[[Category:Drug]]
[[Category:Non-steroidal anti-inflammatory drugs]]
[[Category:Antiseptics]]