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
Understanding the pharmacokinetics of anxiolytic drugs.	2013-04	23330992
Gene expression and mutation assessment provide clues of genetic and epigenetic mechanisms in liver tumors of oxazepam-exposed mice.	2011-07	21147764
Antidepressant/anxiolytic and anti-nociceptive effects of novel 2-substituted 1,4-benzodiazepine-2-ones.	2010-04-15	21179341
Probable trimethoprim/sulfamethoxazole-induced higher-level gait disorder and nocturnal delirium in an elderly man.	2009-01	19109207
Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats.	2008-11	18692521
The putative tumor suppressor Tsc-22 is downregulated early in chemically induced hepatocarcinogenesis and may be a suppressor of Gadd45b.	2007-09	17533171
What every dentist should know about the "z-sedatives".	2007	18069595
Large B-cell lymphoma presenting as acute abdominal pain and spontaneous splenic rupture; a case report and review of relevant literature.	2006-11-28	17129392
On the mechanism of hepatocarcinogenesis of benzodiazepines: evidence that diazepam and oxazepam are CYP2B inducers in rats, and both CYP2B and CYP4A inducers in mice.	2006	16684660
Oxazepam does not modulate the behavioral effects of d-amphetamine in humans.	2005-10	16182353
Unique patterns of gene expression changes in liver after treatment of mice for 2 weeks with different known carcinogens and non-carcinogens.	2005-03	15618236
Chemical-induced atrial thrombosis in NTP rodent studies.	2005	16048847
Pulmonary embolism possibly associated with olanzapine treatment.	2003-12-13	14670884
Changes in global gene and protein expression during early mouse liver carcinogenesis induced by non-genotoxic model carcinogens oxazepam and Wyeth-14,643.	2003-04	12727805
Cardiac risk at the onset of treatment in patients treated with benzodiazepines and clozapine.	2002-11	12547310
Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9.	2002-11	12386133
Concurrent cocaine withdrawal alters alcohol withdrawal symptoms.	2002	12296498
Remission of SSRI-induced akathisia after switch to nefazodone.	2001-07	11488371
Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis.	1999-08-19	10467420
Toxicity and carcinogenicity studies of oxazepam in the Fischer 344 rat.	1998-03	9538042
Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease.	1996-01-01	8700792
Late-onset seizures in alcohol withdrawal.	1995-06	7573789
Nitric oxide-induced motor neuron disease in a patient with alcoholism.	1995-04-13	7885422
(S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7.	1995-02	7773302
Alcohol and benzodiazepines generate anxiety, panic and phobias.	1995-02	7769598
Carcinogenicity studies of oxazepam in mice.	1994-08	7982536
Low frequency of H-ras mutations in hepatocellular adenomas and carcinomas and in hepatoblastomas from B6C3F1 mice exposed to oxazepam in the diet.	1994-05	8200073
Paranoid psychosis induced by oxymetazoline nasal spray.	1994-02-01	8293377
Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers.	1992	1349754
Prenatal oxazepam enhances mouse maternal aggression in the offspring, without modifying acute chlordiazepoxide effects.	1991-01-01	1646381
[Chemical and pharmacologic aspects of benzodiazepines].	1989-07-04	2570451
Acute confusional state with status petit mal as a withdrawal syndrome--and five year follow-up.	1988-03	3365642
Tumor-promoting activity of benzodiazepine tranquilizers, diazepam and oxazepam, in mouse liver.	1986-05	3698206
Short-, medium-, and long-term effects of prenatal oxazepam on neurobehavioural development of mice.	1985	3936103
Abstinence syndrome from therapeutic doses of oxazepam.	1983-11	6418370
Abstinence syndrome from therapeutic doses of oxazepam.	1983-06	6871816
Enhancement of GABA binding by benzodiazepines and related anxiolytics.	1983-05-06	6135616
Oxazepam withdrawal syndrome.	1982-09-04	7132871
Oxazepam withdrawal syndrome.	1982-06-26	6810073
Oxazepam withdrawal syndrome.	1982-04-03	6806585
Structure activity relationships of selected benzodiazepines as anticonvulsants to local anesthetics.	1980	6774348
Seven cases of somnambulism induced by drugs.	1979-07	453369
Floppy-infant syndrome: Is oxazepam the answer?	1977-11-26	73027
[Pharmacologic bases of use of benzodiazepines in peréinatal medicine].	1977-01	851373

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