Oxazepam

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H11ClN2O2
Molecular Weight	286.713
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1N=C(C2=CC=CC=C2)C3=CC(Cl)=CC=C3NC1=O

InChI

InChIKey=ADIMAYPTOBDMTL-UHFFFAOYSA-N

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/h1-8,15,20H,(H,17,19)

HIDE SMILES / InChI

Molecular Formula	C15H11ClN2O2
Molecular Weight	286.713
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=140d8f61-912b-449a-9c34-b52e08b3d819
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/367060 https://www.ncbi.nlm.nih.gov/pubmed/6111408

Oxazepam is the first of a chemical series of compounds, the 3-hydroxybenzodiazepinones. A therapeutic agent providing versatility and flexibility in control of common emotional disturbances, this product exerts prompt action in a wide variety of disorders associated with anxiety, tension, agitation and irritability, and anxiety associated with depression. Oxazepam has distinguished itself clinically from other benzodiazepines by virtue of its excellent tolerance. Because of its excellent tolerance, dosage is very flexible, and it is, therefore, possible to utilize oxazepam in a wide spectrum of anxiety-related disorders including the psychoses. Oxazepam has been administered to humans by the oral route only. Usual ranges for kinetic parameters are: elimination half-life, 5 to 15 hours; volume of distribution, 0.6 to 2.0 L/kg; clearance, 0.9 to 2.0 ml/min/kg. Age and liver disease have a minimal influence on oxazepam kinetics, but renal disease is associated with a prolonged half-life and increased volume of distribution.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6135616	Activator 1447		0.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=140d8f61-912b-449a-9c34-b52e08b3d819	Primary		Approved 8583	OXAZEPAM Approved Use Oxazepam is indicated for the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. Anxiety associated with depression is also responsive to oxazepam therapy. This product has been found particularly useful in the management of anxiety, tension, agitation and irritability in older patients. Alcoholics with acute tremulousness, inebriation, or with anxiety associated with alcohol withdrawal are responsive to therapy. The effectiveness of oxazepam in long-term use, that is, more than 4 months, has not been assessed by systematic clinical studies. The physician should periodically reassess the usefulness of the drug for the individual patient. Launch Date 1988
Acohol withdrawal 6 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=140d8f61-912b-449a-9c34-b52e08b3d819	Primary		Approved 8583	OXAZEPAM Approved Use Oxazepam is indicated for the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. Anxiety associated with depression is also responsive to oxazepam therapy. This product has been found particularly useful in the management of anxiety, tension, agitation and irritability in older patients. Alcoholics with acute tremulousness, inebriation, or with anxiety associated with alcohol withdrawal are responsive to therapy. The effectiveness of oxazepam in long-term use, that is, more than 4 months, has not been assessed by systematic clinical studies. The physician should periodically reassess the usefulness of the drug for the individual patient. Launch Date 1988

C_max

Value	Dose	Co-administered	Analyte	Population
268 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1867967	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		OXAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
288 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7981015	10 mg 3 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OXAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
4737 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7981015	10 mg 3 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OXAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1867967	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		OXAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
5.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1867967	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		OXAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7981015	10 mg 3 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OXAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
4000 mg single, oral Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	unknown, 30 Health Status: unknown Age Group: 30 Sex: M Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	Other AEs: Coma... Other AEs: Coma Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y
200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/	unhealthy, 75 Health Status: unhealthy Age Group: 75 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/	Other AEs: Coma, Blisters... Other AEs: Coma Blisters Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/
3000 mg single, oral Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	unknown Health Status: unknown Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	Other AEs: Drowsiness, Obtundation... Other AEs: Drowsiness Obtundation Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y

AEs

AE	Dose	Population
Coma	4000 mg single, oral Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	unknown, 30 Health Status: unknown Age Group: 30 Sex: M Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y
Blisters	200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/	unhealthy, 75 Health Status: unhealthy Age Group: 75 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/
Coma	200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/	unhealthy, 75 Health Status: unhealthy Age Group: 75 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2231838/
Drowsiness	3000 mg single, oral Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	unknown Health Status: unknown Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y
Obtundation	3000 mg single, oral Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y	unknown Health Status: unknown Sources: https://link.springer.com/article/10.1007/s40278-017-28921-y

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT2 779	UGT1A1 479 UGT1A3 470 UGT2B7 456

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 782	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556614/	yes [Inhibition 20 uM]

Drug as victim

Target	Modality	Activity
UGT1A1 479	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100475/	yes
UGT1A3 470	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100475/	yes
UGT2B7 456	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100475/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7823	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7823
eMolecules	592985	https://www.emolecules.com/cgi-bin/more?vid=592985

PubMed

Title	Date	PubMed
[Pharmacologic bases of use of benzodiazepines in peréinatal medicine].	1977 Jan	851373
Oxazepam withdrawal syndrome.	1982 Apr 3	6806585
Abstinence syndrome from therapeutic doses of oxazepam.	1983 Nov	6418370
Carcinogenicity studies of oxazepam in mice.	1994 Aug	7982536
Paranoid psychosis induced by oxymetazoline nasal spray.	1994 Feb 1	8293377
Low frequency of H-ras mutations in hepatocellular adenomas and carcinomas and in hepatoblastomas from B6C3F1 mice exposed to oxazepam in the diet.	1994 May	8200073
Nitric oxide-induced motor neuron disease in a patient with alcoholism.	1995 Apr 13	7885422
(S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7.	1995 Feb	7773302
Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease.	1996 Jan-Feb	8700792
Toxicity and carcinogenicity studies of oxazepam in the Fischer 344 rat.	1998 Mar	9538042
Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis.	1999 Aug 19	10467420
Concurrent cocaine withdrawal alters alcohol withdrawal symptoms.	2002	12296498
Changes in global gene and protein expression during early mouse liver carcinogenesis induced by non-genotoxic model carcinogens oxazepam and Wyeth-14,643.	2003 Apr	12727805
Chemical-induced atrial thrombosis in NTP rodent studies.	2005	16048847
Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats.	2008 Nov	18692521

Patents

Sample Use Guides

In Vivo Use Guide

Mild-to-moderate anxiety: 10 to 15 mg, 3 or 4 times daily. Severe anxiety syndromes and Alcoholics with acute inebriation, tremulousness, or anxiety on withdrawal: 15 to 30 mg, 3 or 4 times daily. Older patients with anxiety, tension, irritability and agitation: 10 mg, 3 times daily (initial dosage), if necessary, increase cautiously to 15 mg, 3 or 4 times daily.

Route of Administration: Oral

In Vitro Use Guide

On the stretch-induced discharge activity of the isolated crayfish sensory neuron oxazepam only produced depression (less than or equal to 0.5 mM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:45 GMT 2025`
Record UNII	6GOW6DWN2A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXAZEPAM CIV

Preferred Name

English

Oxazepam

Official Name

English

OXAZEPAM [HSDB]

Common Name

English

OXAZEPAM [MART.]

Common Name

English

OXAZEPAM [USAN]

Common Name

English

2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1,3-DIHYDRO-3-HYDROXY-5-PHENYL-, (±)-

Systematic Name

English

OXAZEPAM [USP MONOGRAPH]

Common Name

English

OXAZEPAM [MI]

Common Name

English

NSC-169448

Code

English

OXAZEPAM [IARC]

Common Name

English

TEMAZEPAM IMPURITY, OXAZEPAM- [USP IMPURITY]

Common Name

English

OXAZEPAM CIV [USP-RS]

Common Name

English

SERAX

Brand Name

English

OXAZEPAM [JAN]

Common Name

English

OXAZEPAM [ORANGE BOOK]

Common Name

English

OXAZEPAM [VANDF]

Common Name

English

OXAZEPAM [EP MONOGRAPH]

Common Name

English

ZAXOPAM

Brand Name

English

(±)-7-CHLORO-1,3-DIHYDRO-3-HYDROXY-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONE

Systematic Name

English

TEMAZEPAM IMPURITY B [EP IMPURITY]

Common Name

English

oxazepam [INN]

Common Name

English

WY-3498

Code

English

Oxazepam [WHO-DD]

Common Name

English

J3.308A

Code

English

Classification Tree Code System Code

NDF-RT

N0000175694