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{{Drugbox|
{{Drugbox
|IUPAC_name = ''9-chloro-6-phenyl-2-(2,2,2-trifluoroethyl)-2,5-diazabicyclo''<br />''[5.4.0]undeca-5,8,10,12-tetraen-3-one''
| Watchedfields = changed
| image = Halazepam.svg
| verifiedrevid = 461743655
| width=220
| IUPAC_name = 7-chloro- 5-phenyl- 1-(2,2,2-trifluoroethyl) -1,3-dihydro- 2''H''-1,4-benzodiazepin- 2-one
| image2 = Halazepam3d.png
| image = Halazepam.png| width = 220
| CAS_number=23092-17-3
| image2 = Halazepam0.png
| ATC_prefix=N05
 
| ATC_suffix=BA13
<!--Clinical data-->
| ATC_supplemental=
| tradename =
| PubChem=31640
| Drugs.com = {{drugs.com|CONS|halazepam}}
| DrugBank=APRD01009
| MedlinePlus = a684001
| C=17 | H=12 | Cl=1 | F=3 | N=2 | O=1
| molecular_weight = 352.7
| bioavailability= ?
| metabolism = [[Liver|Hepatic]]
| elimination_half-life= ?
| excretion = [[Kidney|Renal]]
| pregnancy_category = ?
| pregnancy_category = ?
| legal_status = [[Schedule IV controlled substance|Schedule IV]] (US)
| legal_status = [[Schedule IV controlled substance|Schedule IV]] (US)
| routes_of_administration= Oral
| routes_of_administration = Oral
 
<!--Pharmacokinetic data-->
| bioavailability = ?
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 14 hours (drug), 50-100 hours (metabolites).
| excretion = [[Kidney|Renal]]
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 23092-17-3
| ATC_prefix = N05
| ATC_suffix = BA13
| PubChem = 31640
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00801
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 29343
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 320YC168LF
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00338
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 970
 
<!--Chemical data-->
| C=17 | H=12 | Cl=1 | F=3 | N=2 | O=1
| molecular_weight = 352.7
| smiles = FC(F)(CN1C(CN=C(C2=CC=CC=C2)C3=C1C=CC(Cl)=C3)=O)F
| InChI = 1/C17H12ClF3N2O/c18-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)22-9-15(24)23(14)10-17(19,20)21/h1-8H,9-10H2
| InChIKey = WYCLKVQLVUQKNZ-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H12ClF3N2O/c18-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)22-9-15(24)23(14)10-17(19,20)21/h1-8H,9-10H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WYCLKVQLVUQKNZ-UHFFFAOYSA-N
| synonyms = <small>9-chloro- 6-phenyl- 2-(2,2,2-trifluoroethyl)- 2,5-diazabicyclo[5.4.0] undeca- 5,8,10,12-tetraen -3-one</small>
}}
}}
'''Halazepam''' is a [[benzodiazepine]] derivative. It possesses [[anxiolytic]], [[anticonvulsant]], [[sedative]] and [[skeletal muscle relaxant]] properties. It is a trifluoromethyl derivative of [[nordazepam]].<ref name=derivation>{{cite journal | first = D. J. | last = Greenblatt | coauthors = A. Locniskar and R. I. Shader | date = [[June 12]], [[1982]] | title = Halazepam, another precursor of desmethyldiazepam | journal = Lancet | volume = 1 | issue = 8285 | pages = 1358-9 | id = {{PMID|6123659}}}}</ref> While its structure may be similar to [[chlordiazepoxide]] and [[diazepam]], it has both less toxicity and less tendency to cause paradoxical hostility and aggression than either of them.<ref name=kinder_gentler_benzo>{{cite journal | first = W. E. | last = Fann | coauthors = W. M. Pitts and J. C. Wheless | month = Mar-Apr | year = 1982 | title = Pharmacology, efficacy, and adverse effects of halazepam, a new benzodiazepine | journal = Pharmacotherapy | volume = 2 | issue = 2 | pages = 72-9 | id = {{PMID|6152591}}}}</ref>
'''Halazepam''' is a [[benzodiazepine]] derivative that was marketed under the brand names '''Paxipam''' in the United States,<ref name=DrugsH />  '''Alapryl''' in Spain,<ref name=DrugsA>{{cite web|title=Alapryl|url=http://www.drugs.com/international/alapryl.html|publisher=Drugs.com|accessdate=December 11, 2014}}</ref> and '''Pacinone''' in Portugal.<ref name=DrugsP>{{cite web|title=Pacinone|url=http://www.drugs.com/international/pacinone.html|publisher=Drugs.com|accessdate=December 11, 2014}}</ref>
==References==
 
<div class="references-small"><references/></div>
==Medical uses==
Halazepam was used for the treatment of [[anxiety]].<ref name=DrugsH />
 
==Adverse effects==
Adverse effects include drowsiness, confusion, dizziness, and sedation.  Gastrointestinal side effects have also been reported including dry mouth and nausea.<ref name=DrugsH />
 
==Pharmacokinetics and pharmacodynamics==
Pharmacokinetics and pharmacodynamics were listed in ''Current Psychotherapeutic Drugs'' published in June 15, 1998 as follows:<ref>{{cite book|last1=Quitkin|first1=Frederick M.  ... |title=Current therapeutic drugs|date=1998|publisher=American Psychiatric Press|location=Washington|isbn=0880489944|page=166|edition=2nd ed.}}</ref>
 
{| class="wikitable"
|-
|Onset of action || Intermediate to slow
|-
| Plasma half life || 14 hr for parent drug and 30-100 hr for its metabolite
|-
| Peak plasma levels || 1-3 hr for parent drug and 3-6 hf for its metabolite
|-
| Metabolism || Metabolized into desmethyldiazepam and 3-hydroxyhalazepam (in the liver)
|-
| Excretion || Excreted through kidneys
|-
| Protein binding|| 98% bound to plasma protein
|}
 
==Regulatory Information==
Halazepam is classified as a [[Controlled_Substances_Act#Schedule_IV_controlled_substances|schedule 4]] [[controlled substance]] with a corresponding code 2762 by the [[Drug Enforcement Administration]] (DEA).<ref name=DEA>{{cite web|title=SCHEDULES OF CONTROLLED SUBSTANCES|url=http://www.gpo.gov/fdsys/pkg/CFR-2012-title21-vol9/xml/CFR-2012-title21-vol9-part1308.xml|publisher=Code of Federal Reguations|accessdate=December 12, 2014|pages=§ 1308.14 Schedule IV|date=2012-04-01}}</ref>
 
==Commercial production==
Halazepam was invented by Schlesinger Walter in the U.S. It was marketed as an anti-anxiety agent in 1981. However, Halazepam is not commercially available in the United States because it was withdrawn by its manufacturer for poor sales.<ref name=DrugsH>{{cite web|title=halazepam|url=http://www.drugs.com/mtm/halazepam.html|publisher=Drugs.com|accessdate=December 11, 2014}}</ref>
 
==See also==
==See also==
*[[nordazepam]]
*[[diazepam]]
*[[chlordiazepoxide]]
*[[Benzodiazepine]]s
*[[Benzodiazepine]]s
==External links==
*[[Nordazepam]]
* [http://www.inchem.org/documents/pims/pharm/pim160.htm Inchem - Halazepam]
*[[Diazepam]]
*[[Chlordiazepoxide]]
*[[Quazepam]]
 
==References==
{{Reflist|2}}


{{Benzodiazepines}}
{{Benzodiazepines}}
{{Anxiolytics}}
{{Anxiolytics}}
[[Category:Anticonvulsants]]
{{GABAAR PAMs}}
[[Category:Anxiolytics]]
 
[[Category:Benzodiazepines]]
[[Category:Benzodiazepines]]
[[Category:Hypnotics]]
[[Category:Organochlorides]]
[[Category:Muscle relaxants]]
[[Category:Organofluorides]]
[[Category:Sedatives]]
[[Category:Lactams]]
 
[[Category:GABAA receptor positive allosteric modulators]]
 
[[Category:Drug]]
{{pharma-stub}}
 
[[pt:Halazepam]]
[[sv:Halazepam]]
{{WikiDoc Sources}}

Revision as of 14:19, 13 April 2015

Halazepam
Clinical data
Synonyms9-chloro- 6-phenyl- 2-(2,2,2-trifluoroethyl)- 2,5-diazabicyclo[5.4.0] undeca- 5,8,10,12-tetraen -3-one
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa684001
Pregnancy
category
  • ?
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life14 hours (drug), 50-100 hours (metabolites).
ExcretionRenal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC17H12ClF3N2O
Molar mass352.7
3D model (JSmol)
  (verify)

Halazepam is a benzodiazepine derivative that was marketed under the brand names Paxipam in the United States,[1] Alapryl in Spain,[2] and Pacinone in Portugal.[3]

Medical uses

Halazepam was used for the treatment of anxiety.[1]

Adverse effects

Adverse effects include drowsiness, confusion, dizziness, and sedation. Gastrointestinal side effects have also been reported including dry mouth and nausea.[1]

Pharmacokinetics and pharmacodynamics

Pharmacokinetics and pharmacodynamics were listed in Current Psychotherapeutic Drugs published in June 15, 1998 as follows:[4]

Onset of action Intermediate to slow
Plasma half life 14 hr for parent drug and 30-100 hr for its metabolite
Peak plasma levels 1-3 hr for parent drug and 3-6 hf for its metabolite
Metabolism Metabolized into desmethyldiazepam and 3-hydroxyhalazepam (in the liver)
Excretion Excreted through kidneys
Protein binding 98% bound to plasma protein

Regulatory Information

Halazepam is classified as a schedule 4 controlled substance with a corresponding code 2762 by the Drug Enforcement Administration (DEA).[5]

Commercial production

Halazepam was invented by Schlesinger Walter in the U.S. It was marketed as an anti-anxiety agent in 1981. However, Halazepam is not commercially available in the United States because it was withdrawn by its manufacturer for poor sales.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "halazepam". Drugs.com. Retrieved December 11, 2014.
  2. ↑ "Alapryl". Drugs.com. Retrieved December 11, 2014.
  3. ↑ "Pacinone". Drugs.com. Retrieved December 11, 2014.
  4. ↑ Quitkin, Frederick M. ... (1998). Current therapeutic drugs (2nd ed. ed.). Washington: American Psychiatric Press. p. 166. ISBN 0880489944.
  5. ↑ "SCHEDULES OF CONTROLLED SUBSTANCES". Code of Federal Reguations. 2012-04-01. pp. § 1308.14 Schedule IV. Retrieved December 12, 2014.

Template:Benzodiazepines Template:Anxiolytics Template:GABAAR PAMs

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