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Details

Stereochemistry RACEMIC
Molecular Formula C15H11ClN2O2
Molecular Weight 286.7135
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXAZEPAM

SMILES

c1ccc(cc1)C2=NC(C(=Nc3ccc(cc32)Cl)O)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 286.7135
Charge 0
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.

Originator

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.5 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

5.7732478E11
Primary
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

5.7732478E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
288 ng/mL
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
268 ng/mL
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4737 ng × h/mL
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
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
2%
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
5.1%
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
Doses

Doses

DosePopulationAdverse events​
4000 mg single, oral
Dose: 4000 mg
Route: oral
Route: single
Dose: 4000 mg
Sources:
unknown, 30
n = 1
Health Status: unknown
Age Group: 30
Sex: M
Population Size: 1
Sources:
Other AEs: Coma...
200 mg single, oral
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 75
n = 1
Health Status: unhealthy
Condition: depression following a coronary bypass operation
Age Group: 75
Sex: M
Population Size: 1
Sources:
Other AEs: Coma, Blisters...
Other AEs:
Coma
Blisters
Sources:
3000 mg single, oral
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Other AEs: Drowsiness, Obtundation...
Other AEs:
Drowsiness
Obtundation
Sources:
AEs

AEs

AESignificanceDosePopulation
Coma
4000 mg single, oral
Dose: 4000 mg
Route: oral
Route: single
Dose: 4000 mg
Sources:
unknown, 30
n = 1
Health Status: unknown
Age Group: 30
Sex: M
Population Size: 1
Sources:
Blisters
200 mg single, oral
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 75
n = 1
Health Status: unhealthy
Condition: depression following a coronary bypass operation
Age Group: 75
Sex: M
Population Size: 1
Sources:
Coma
200 mg single, oral
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 75
n = 1
Health Status: unhealthy
Condition: depression following a coronary bypass operation
Age Group: 75
Sex: M
Population Size: 1
Sources:
Drowsiness
3000 mg single, oral
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Obtundation
3000 mg single, oral
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Inhibition 20 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
[Pharmacologic bases of use of benzodiazepines in peréinatal medicine].
1977 Jan
Floppy-infant syndrome: Is oxazepam the answer?
1977 Nov 26
Seven cases of somnambulism induced by drugs.
1979 Jul
Oxazepam withdrawal syndrome.
1982 Apr 3
Oxazepam withdrawal syndrome.
1982 Jun 26
Enhancement of GABA binding by benzodiazepines and related anxiolytics.
1983 May 6
[Chemical and pharmacologic aspects of benzodiazepines].
1989 Jul 4
Prenatal oxazepam enhances mouse maternal aggression in the offspring, without modifying acute chlordiazepoxide effects.
1991 Jan-Feb
Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers.
1992
Carcinogenicity studies of oxazepam in mice.
1994 Aug
Paranoid psychosis induced by oxymetazoline nasal spray.
1994 Feb 1
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
Nitric oxide-induced motor neuron disease in a patient with alcoholism.
1995 Apr 13
(S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7.
1995 Feb
Alcohol and benzodiazepines generate anxiety, panic and phobias.
1995 Feb
Late-onset seizures in alcohol withdrawal.
1995 Jun
Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease.
1996 Jan-Feb
Toxicity and carcinogenicity studies of oxazepam in the Fischer 344 rat.
1998 Mar
Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis.
1999 Aug 19
Remission of SSRI-induced akathisia after switch to nefazodone.
2001 Jul
Concurrent cocaine withdrawal alters alcohol withdrawal symptoms.
2002
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
Chemical-induced atrial thrombosis in NTP rodent studies.
2005
Oxazepam does not modulate the behavioral effects of d-amphetamine in humans.
2005 Oct
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
Large B-cell lymphoma presenting as acute abdominal pain and spontaneous splenic rupture; a case report and review of relevant literature.
2006 Nov 28
What every dentist should know about the "z-sedatives".
2007 Fall
The putative tumor suppressor Tsc-22 is downregulated early in chemically induced hepatocarcinogenesis and may be a suppressor of Gadd45b.
2007 Sep
Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats.
2008 Nov
Probable trimethoprim/sulfamethoxazole-induced higher-level gait disorder and nocturnal delirium in an elderly man.
2009 Jan
Antidepressant/anxiolytic and anti-nociceptive effects of novel 2-substituted 1,4-benzodiazepine-2-ones.
2010 Apr-Jun
Gene expression and mutation assessment provide clues of genetic and epigenetic mechanisms in liver tumors of oxazepam-exposed mice.
2011 Jul
Understanding the pharmacokinetics of anxiolytic drugs.
2013 Apr
Patents

Sample Use Guides

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 Fri Jun 25 20:35:30 UTC 2021
Edited
by admin
on Fri Jun 25 20:35:30 UTC 2021
Record UNII
6GOW6DWN2A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXAZEPAM
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
OXAZEPAM [HSDB]
Common Name English
OXAZEPAM CIV
USP-RS  
Common Name English
OXAZEPAM [MART.]
Common Name English
OXAZEPAM [WHO-DD]
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 [MI]
Common Name English
NSC-169448
Code English
OXAZEPAM [IARC]
Common Name English
OXAZEPAM CIV [USP-RS]
Common Name English
TEMAZEPAM SPECIFIED IMPURITY B [EP]
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
OXAZEPAM [USP]
Common Name English
(+/-)-7-CHLORO-1,3-DIHYDRO-3-HYDROXY-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONE
Systematic Name English
TEMAZEPAM IMPURITY, OXAZEPAM- [USP]
Common Name English
OXAZEPAM [INN]
Common Name English
WY-3498
Code English
J3.308A
Code English
Classification Tree Code System Code
NDF-RT N0000175694
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
DEA NO. 2835
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
NCI_THESAURUS C1012
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
WHO-ATC N05BA04
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
NDF-RT N0000007542
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
WHO-VATC QN05BA04
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
LIVERTOX 721
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
Code System Code Type Description
PUBCHEM
4616
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
CAS
604-75-1
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
WIKIPEDIA
OXAZEPAM
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
MERCK INDEX
M8295
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL568
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
EPA CompTox
604-75-1
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
DRUG CENTRAL
2015
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
LACTMED
Oxazepam
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
RXCUI
7781
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY RxNorm
HSDB
3140
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
USP_CATALOG
1483006
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00842
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
MESH
D010076
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
EVMPD
SUB09506MIG
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
INN
1507
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
FDA UNII
6GOW6DWN2A
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
NCI_THESAURUS
C47642
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
IUPHAR
7253
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
210-076-9
Created by admin on Fri Jun 25 20:35:30 UTC 2021 , Edited by admin on Fri Jun 25 20:35:30 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
PARENT -> METABOLITE
TRACE IN URINE; NOT IN PLASMA
MINOR
URINE
PARENT -> METABOLITE ACTIVE
PARENT -> METABOLITE ACTIVE
Related Record Type Details
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.1
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 4.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC