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
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)
Molecular Formula | C15H11ClN2O2 |
Molecular Weight | 286.713 |
Charge | 0 |
Count |
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Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=140d8f61-912b-449a-9c34-b52e08b3d819Curator'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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6135616 |
0.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | OXAZEPAM Approved UseOxazepam 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 Date1988 |
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Primary | OXAZEPAM Approved UseOxazepam 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 Date1988 |
Cmax
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 |
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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 |
T1/2
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 |
Funbound
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: |
unknown, 30 Health Status: unknown Age Group: 30 Sex: M Sources: |
Other AEs: Coma... |
200 mg single, oral |
unhealthy, 75 |
Other AEs: Coma, Blisters... |
3000 mg single, oral Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: |
unknown |
Other AEs: Drowsiness, Obtundation... Other AEs: Drowsiness Sources: Obtundation |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Coma | 4000 mg single, oral Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: |
unknown, 30 Health Status: unknown Age Group: 30 Sex: M Sources: |
|
Blisters | 200 mg single, oral |
unhealthy, 75 |
|
Coma | 200 mg single, oral |
unhealthy, 75 |
|
Drowsiness | 3000 mg single, oral Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: |
unknown |
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Obtundation | 3000 mg single, oral Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: |
unknown |
PubMed
Title | Date | PubMed |
---|---|---|
[Pharmacologic bases of use of benzodiazepines in peréinatal medicine]. | 1977 Jan |
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Oxazepam withdrawal syndrome. | 1982 Apr 3 |
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Abstinence syndrome from therapeutic doses of oxazepam. | 1983 Nov |
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Carcinogenicity studies of oxazepam in mice. | 1994 Aug |
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Paranoid psychosis induced by oxymetazoline nasal spray. | 1994 Feb 1 |
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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 |
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Nitric oxide-induced motor neuron disease in a patient with alcoholism. | 1995 Apr 13 |
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(S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7. | 1995 Feb |
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Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. | 1996 Jan-Feb |
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Toxicity and carcinogenicity studies of oxazepam in the Fischer 344 rat. | 1998 Mar |
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Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis. | 1999 Aug 19 |
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Concurrent cocaine withdrawal alters alcohol withdrawal symptoms. | 2002 |
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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 |
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Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats. | 2008 Nov |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6148246
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
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Record UNII |
6GOW6DWN2A
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Validated (UNII)
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NDF-RT |
N0000175694
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DEA NO. |
2835
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NCI_THESAURUS |
C1012
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WHO-ATC |
N05BA04
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NDF-RT |
N0000007542
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WHO-VATC |
QN05BA04
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LIVERTOX |
NBK548104
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7823
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4616
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604-75-1
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OXAZEPAM
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169448
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m8295
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CHEMBL568
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DTXSID1021087
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2015
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6GOW6DWN2A
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Oxazepam
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7781
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3140
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1483006
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6GOW6DWN2A
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C47642
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7253
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100000091921
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210-076-9
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE | |||
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PARENT -> METABOLITE ACTIVE | |||
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PARENT -> METABOLITE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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PARENT -> IMPURITY | |||
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.1
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 4.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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