OXAZEPAM MONOSODIUM SUCCINATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H14ClN2O5.Na
Molecular Weight	408.768
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of OXAZEPAM MONOSODIUM SUCCINATE

Structure Search

SMILES

[Na+].[O-]C(=O)CCC(=O)OC1N=C(C2=CC=CC=C2)C3=C(NC1=O)C=CC(Cl)=C3

InChI

InChIKey=HLXIPDOKNUEODM-UHFFFAOYSA-M

InChI=1S/C19H15ClN2O5.Na/c20-12-6-7-14-13(10-12)17(11-4-2-1-3-5-11)22-19(18(26)21-14)27-16(25)9-8-15(23)24;/h1-7,10,19H,8-9H2,(H,21,26)(H,23,24);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C19H14ClN2O5
Molecular Weight	385.778
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6135616	Activator 1430		0.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=140d8f61-912b-449a-9c34-b52e08b3d819	Primary		Approved 8429	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 8429	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
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
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

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
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
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

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 n = 1 Health Status: unknown Age Group: 30 Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: depression following a coronary bypass operation Age Group: 75 Sex: M Population Size: 1 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 n = 1 Health Status: unknown Population Size: 1 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 n = 1 Health Status: unknown Age Group: 30 Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: depression following a coronary bypass operation Age Group: 75 Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: depression following a coronary bypass operation Age Group: 75 Sex: M Population Size: 1 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 n = 1 Health Status: unknown Population Size: 1 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 n = 1 Health Status: unknown Population Size: 1 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 647	UGT1A1 418 UGT1A3 422 UGT2B7 389

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 648	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556614/	yes [Inhibition 20 uM]

Drug as victim

Target	Modality	Activity
UGT1A1 418	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100475/	yes
UGT1A3 422	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3100475/	yes
UGT2B7 389	substrate 3367 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
Floppy-infant syndrome: Is oxazepam the answer?	1977 Nov 26	73027
Seven cases of somnambulism induced by drugs.	1979 Jul	453369
Oxazepam withdrawal syndrome.	1982 Sep 4	7132871
Abstinence syndrome from therapeutic doses of oxazepam.	1983 Nov	6418370
Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers.	1992	1349754
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
Concurrent cocaine withdrawal alters alcohol withdrawal symptoms.	2002	12296498
Pulmonary embolism possibly associated with olanzapine treatment.	2003 Dec 13	14670884
What every dentist should know about the "z-sedatives".	2007 Fall	18069595
The putative tumor suppressor Tsc-22 is downregulated early in chemically induced hepatocarcinogenesis and may be a suppressor of Gadd45b.	2007 Sep	17533171
Understanding the pharmacokinetics of anxiolytic drugs.	2013 Apr	23330992

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 `Fri Dec 15 15:03:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:03:57 GMT 2023`
Record UNII	12HJD2925Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXAZEPAM MONOSODIUM SUCCINATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1012