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: WARNINGSchedule 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.^[7]^[8] Oxazepam is used for the treatment of anxiety,^[9]^[10] insomnia, and to control symptoms of alcohol withdrawal syndrome.

It is a metabolite of diazepam, prazepam, and temazepam,^[11] and has moderate amnesic, anxiolytic, anticonvulsant, hypnotic, sedative, and skeletal muscle relaxant properties compared to other benzodiazepines.^[12]

It was patented in 1962 and approved for medical use in 1964.^[13]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ 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.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[2] 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.

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

[pmid3197746-4] 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-5] 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.

[6] CID 4616 from PubChem

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

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

[9] 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.

[10] 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.

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

[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.

[Fis2006-13] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 536. ISBN 9783527607495.

[2]

[1]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

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)^[2] CA: Schedule IV DE: Prescription only (Anlage III for higher doses) US: WARNING^[1]Schedule IV Prescription drug
Pharmacokinetic data
Bioavailability	92.8%
Metabolism	Hepatic (glucuronidation)
Onset of action	30 - 120 minutes
Elimination half-life	6–9 hours^[3]^[4]^[5]
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^[6]
CAS Number	604-75-1
PubChem CID	4616
IUPHAR/BPS	7253
DrugBank	DB00842^Y
ChemSpider	4455^Y
UNII	6GOW6DWN2A
KEGG	D00464^Y
ChEBI	CHEBI:7823^Y
ChEMBL	ChEMBL568^Y
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^N Key:IMAUTQQURLXUGJ-UHFFFAOYSA-N^N
(verify)

Our website is made possible by displaying online advertisements to our visitors. Please consider supporting us by disabling your ad blocker.

Oxazepam

Our website is made possible by displaying online advertisements to our visitors.
Please consider supporting us by disabling your ad blocker.