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Details

Stereochemistry RACEMIC
Molecular Formula C15H10ClN2O2.K
Molecular Weight 324.803
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Oxazepam potassium

SMILES

[K+].OC1N=C(C2=CC=CC=C2)C3=CC(Cl)=CC=C3[N-]C1=O

InChI

InChIKey=PKBAMHLVQAMVSC-UHFFFAOYSA-M
InChI=1S/C15H11ClN2O2.K/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,17,18,19);/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula K
Molecular Weight 39.0983
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C15H10ClN2O2
Molecular Weight 285.705
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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

Bell, S.C.|Childress, S.J.
6
Sources: Bell S.C., Childress S.J. (1962) A rearrangement of 5- aryl- 1,3-dihydro-2H- 1,4-benzodiazepine-2-one 4-oxides. J. Org. Chem., 27, 1691-1695.
Curator's Comment: Reference was retrieved from https://monographs.iarc.fr/ENG/Monographs/vol66/mono66-9.pdf

Approval Year

1965
159
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1447
 0.5 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OCT2
779
UGT1A1
479

UGT1A3
470

UGT2B7
456
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OCT2
782
 yes [Inhibition 20 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT1A1
479
 yes
UGT1A3
470
 yes
UGT2B7
456
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Understanding the pharmacokinetics of anxiolytic drugs.
2013-04
Gene expression and mutation assessment provide clues of genetic and epigenetic mechanisms in liver tumors of oxazepam-exposed mice.
2011-07
Antidepressant/anxiolytic and anti-nociceptive effects of novel 2-substituted 1,4-benzodiazepine-2-ones.
2010-04-15
Probable trimethoprim/sulfamethoxazole-induced higher-level gait disorder and nocturnal delirium in an elderly man.
2009-01
Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats.
2008-11
The putative tumor suppressor Tsc-22 is downregulated early in chemically induced hepatocarcinogenesis and may be a suppressor of Gadd45b.
2007-09
What every dentist should know about the "z-sedatives".
2007
Large B-cell lymphoma presenting as acute abdominal pain and spontaneous splenic rupture; a case report and review of relevant literature.
2006-11-28
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
Oxazepam does not modulate the behavioral effects of d-amphetamine in humans.
2005-10
Unique patterns of gene expression changes in liver after treatment of mice for 2 weeks with different known carcinogens and non-carcinogens.
2005-03
Chemical-induced atrial thrombosis in NTP rodent studies.
2005
Pulmonary embolism possibly associated with olanzapine treatment.
2003-12-13
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
Cardiac risk at the onset of treatment in patients treated with benzodiazepines and clozapine.
2002-11
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
Concurrent cocaine withdrawal alters alcohol withdrawal symptoms.
2002
Remission of SSRI-induced akathisia after switch to nefazodone.
2001-07
Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis.
1999-08-19
Toxicity and carcinogenicity studies of oxazepam in the Fischer 344 rat.
1998-03
Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease.
1996-01-01
Late-onset seizures in alcohol withdrawal.
1995-06
Nitric oxide-induced motor neuron disease in a patient with alcoholism.
1995-04-13
(S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7.
1995-02
Alcohol and benzodiazepines generate anxiety, panic and phobias.
1995-02
Carcinogenicity studies of oxazepam in mice.
1994-08
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
Paranoid psychosis induced by oxymetazoline nasal spray.
1994-02-01
Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers.
1992
Prenatal oxazepam enhances mouse maternal aggression in the offspring, without modifying acute chlordiazepoxide effects.
1991-01-01
[Chemical and pharmacologic aspects of benzodiazepines].
1989-07-04
Acute confusional state with status petit mal as a withdrawal syndrome--and five year follow-up.
1988-03
Tumor-promoting activity of benzodiazepine tranquilizers, diazepam and oxazepam, in mouse liver.
1986-05
Short-, medium-, and long-term effects of prenatal oxazepam on neurobehavioural development of mice.
1985
Abstinence syndrome from therapeutic doses of oxazepam.
1983-11
Abstinence syndrome from therapeutic doses of oxazepam.
1983-06
Enhancement of GABA binding by benzodiazepines and related anxiolytics.
1983-05-06
Oxazepam withdrawal syndrome.
1982-09-04
Oxazepam withdrawal syndrome.
1982-06-26
Oxazepam withdrawal syndrome.
1982-04-03
Structure activity relationships of selected benzodiazepines as anticonvulsants to local anesthetics.
1980
Seven cases of somnambulism induced by drugs.
1979-07
Floppy-infant syndrome: Is oxazepam the answer?
1977-11-26
[Pharmacologic bases of use of benzodiazepines in peréinatal medicine].
1977-01
Patents

Patents

WO/1987/000428A1
6

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 Wed Apr 02 10:49:47 GMT 2025
Edited
by admin
on Wed Apr 02 10:49:47 GMT 2025
Record UNII
U24E5Y7BVU
Record Status Validated (UNII)
Record Version
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Name Type Language
Oxazepam potassium
Common Name English
2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-, monopotassium salt
Preferred Name English
2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-, potassium salt (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
U24E5Y7BVU
Created by admin on Wed Apr 02 10:49:47 GMT 2025 , Edited by admin on Wed Apr 02 10:49:47 GMT 2025
PRIMARY
CAS
75696-06-9
Created by admin on Wed Apr 02 10:49:47 GMT 2025 , Edited by admin on Wed Apr 02 10:49:47 GMT 2025
PRIMARY
PUBCHEM
164512941
Created by admin on Wed Apr 02 10:49:47 GMT 2025 , Edited by admin on Wed Apr 02 10:49:47 GMT 2025
PRIMARY
Related Record Type Details
Structure of Oxazepam
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of Oxazepam
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