Oxazepam

Oxazepam
Clinical data
Pronunciation	/ɒkˈsæzɪpæm/; ok-SAZ-i-pam
Trade names	Serax, Alepam, Serepax, others
Addiction; liability	Low–moderate
Routes of; administration	By mouth
Drug class	Benzodiazepine
ATC code	N05BA04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Prescription only (Anlage III for higher doses); US: Schedule IV; Prescription drug;
Pharmacokinetic data
Bioavailability	92.8%
Metabolism	Hepatic (glucuronidation)
Onset of action	30 - 120 minutes
Elimination half-life	6–9 hours
Duration of action	6 - 12 hours
Excretion	Renal
Identifiers
	IUPAC name (RS)-7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one;
CAS Number	604-75-1;
PubChem CID	4616;
IUPHAR/BPS	7253;
DrugBank	DB00842 ;
ChemSpider	4455 ;
UNII	6GOW6DWN2A;
KEGG	D00464 ;
ChEBI	CHEBI:7823 ;
ChEMBL	ChEMBL568 ;
CompTox Dashboard (EPA)	DTXSID1021087 ;
ECHA InfoCard	100.009.161
Chemical and physical data
Formula	C15H11ClN2O2
Molar mass	286.71 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	205 to 206 °C (401 to 403 °F)
	SMILES O=C1Nc2ccc(Cl)cc2C(c2ccccc2)=NC1O;
	InChI InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,18,20H ; Key:IMAUTQQURLXUGJ-UHFFFAOYSA-N ;
	(verify)

Oxazepam is a short-to-intermediate-acting benzodiazepine.^[6]^[7] Oxazepam is used for the treatment of anxiety,^[8]^[9] insomnia, and to control symptoms of alcohol withdrawal syndrome.

It is a metabolite of diazepam, prazepam, and temazepam,^[10] and has moderate amnesic, anxiolytic, anticonvulsant, hypnotic, sedative, and skeletal muscle relaxant properties compared to other benzodiazepines.^[11]

It was patented in 1962 and approved for medical use in 1964.^[12]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Encadré 1. Anxiolytiques à demi-vie courte (< 20 heures) et sans métabolite actif par ordre alphabétique de DCI
^ Sonne J, Loft S, Døssing M, Vollmer-Larsen A, Olesen KL, Victor M, et al. (1988). "Bioavailability and pharmacokinetics of oxazepam". European Journal of Clinical Pharmacology. 35 (4): 385–389. doi:10.1007/bf00561369. PMID 3197746. S2CID 31007311.
^ Sonne J, Boesgaard S, Poulsen HE, Loft S, Hansen JM, Døssing M, Andreasen F (November 1990). "Pharmacokinetics and pharmacodynamics of oxazepam and metabolism of paracetamol in severe hypothyroidism". British Journal of Clinical Pharmacology. 30 (5): 737–742. doi:10.1111/j.1365-2125.1990.tb03844.x. PMC 1368175. PMID 2271373.
^ CID 4616 from PubChem
^ "Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2008-12-29.
^ "FASS". Läkemedelsindustriföreningens Service AB. Archived from the original on 2011-10-01. Retrieved 2011-02-03.
^ Janecek J, Vestre ND, Schiele BC, Zimmermann R (December 1966). "Oxazepam in the treatment of anxiety states: a controlled study". Journal of Psychiatric Research. 4 (3): 199–206. doi:10.1016/0022-3956(66)90007-0. PMID 20034170.
^ Sarris J, Scholey A, Schweitzer I, Bousman C, Laporte E, Ng C, et al. (May 2012). "The acute effects of kava and oxazepam on anxiety, mood, neurocognition; and genetic correlates: a randomized, placebo-controlled, double-blind study". Human Psychopharmacology. 27 (3): 262–269. doi:10.1002/hup.2216. PMID 22311378. S2CID 44801451.
^ "Oxazepam (IARC Summary & Evaluation, Volume 66, 1996)". IARC. Archived from the original on 2008-09-07. Retrieved 2009-03-12.
^ Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–844. doi:10.2174/138920008786049258. PMID 18855614. Archived from the original on 2009-03-17.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 536. ISBN 9783527607495.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] Encadré 1. Anxiolytiques à demi-vie courte (< 20 heures) et sans métabolite actif par ordre alphabétique de DCI

[pmid3197746-3] Sonne J, Loft S, Døssing M, Vollmer-Larsen A, Olesen KL, Victor M, et al. (1988). "Bioavailability and pharmacokinetics of oxazepam". European Journal of Clinical Pharmacology. 35 (4): 385–389. doi:10.1007/bf00561369. PMID 3197746. S2CID 31007311.

[Pharmacokinetics_and_pharmacodynami-4] Sonne J, Boesgaard S, Poulsen HE, Loft S, Hansen JM, Døssing M, Andreasen F (November 1990). "Pharmacokinetics and pharmacodynamics of oxazepam and metabolism of paracetamol in severe hypothyroidism". British Journal of Clinical Pharmacology. 30 (5): 737–742. doi:10.1111/j.1365-2125.1990.tb03844.x. PMC 1368175. PMID 2271373.

[5] CID 4616 from PubChem

[6] "Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2008-12-29.

[7] "FASS". Läkemedelsindustriföreningens Service AB. Archived from the original on 2011-10-01. Retrieved 2011-02-03.

[8] Janecek J, Vestre ND, Schiele BC, Zimmermann R (December 1966). "Oxazepam in the treatment of anxiety states: a controlled study". Journal of Psychiatric Research. 4 (3): 199–206. doi:10.1016/0022-3956(66)90007-0. PMID 20034170.

[9] Sarris J, Scholey A, Schweitzer I, Bousman C, Laporte E, Ng C, et al. (May 2012). "The acute effects of kava and oxazepam on anxiety, mood, neurocognition; and genetic correlates: a randomized, placebo-controlled, double-blind study". Human Psychopharmacology. 27 (3): 262–269. doi:10.1002/hup.2216. PMID 22311378. S2CID 44801451.

[10] "Oxazepam (IARC Summary & Evaluation, Volume 66, 1996)". IARC. Archived from the original on 2008-09-07. Retrieved 2009-03-12.

[11] Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–844. doi:10.2174/138920008786049258. PMID 18855614. Archived from the original on 2009-03-17.

[Fis2006-12] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 536. ISBN 9783527607495.

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