Oxazepam

Oxazepam

Clinical data
Routes of administration	Oral
ATC code	N05BA04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV DE: Anlage III (Prescription only) US: Schedule IV
Pharmacokinetic data
Bioavailability	95.5%
Metabolism	Hepatic
Biological half-life	5–15 h
Excretion	Renal
Identifiers
IUPAC name 7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number	604-75-1
PubChem CID	4616
IUPHAR/BPS	7253
DrugBank	DB00842 Y
ChemSpider	4455 Y
UNII	6GOW6DWN2A
KEGG	D00464 Y
ChEBI	CHEBI:7823 Y
ChEMBL	CHEMBL568 Y
ECHA InfoCard	100.009.161
Chemical and physical data
Formula	C15H11ClN2O2
Molar mass	286.71 g·mol−1
3D model (Jmol)	Interactive image
Melting point	205 to 206 °C (401 to 403 °F)
SMILES OC1N=C(C2=C(NC1=O)C=CC(Cl)=C2)C3=CC=CC=C3
InChI 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/h1-8,15,18,20H N Key:IMAUTQQURLXUGJ-UHFFFAOYSA-N N

Oxazepam is a short-to-intermediate-acting benzodiazepine. Oxazepam is used for the treatment of anxiety and insomnia and in the control of symptoms of alcohol withdrawal.

It is a metabolite of diazepam, prazepam, and temazepam, and has moderate amnesic, anxiolytic, anticonvulsant, hypnotic, sedative, and skeletal muscle relaxant properties compared to other benzodiazepines. Oxazepam was initially patented and marketed in 1965.

It is an intermediate-acting benzodiazepine with a slow onset of action, so it is usually prescribed to individuals who have trouble staying asleep, rather than falling asleep. It is commonly prescribed for anxiety disorders with associated tension, irritability, and agitation. It is also prescribed for drug and alcohol withdrawal, and for anxiety associated with depression. Physicians may use oxazepam outside its approved indications to treat social phobia, post-traumatic stress disorder, insomnia, premenstrual syndrome, and other conditions.

Oxazepam, along with diazepam, nitrazepam, and temazepam, were the four benzodiazepines listed on the pharmaceutical benefits scheme and represented 82% of the benzodiazepine prescriptions in Australia in 1990-1991.

The side effects of oxazepam are similar to those of other benzodiazepines, and may include dizziness, drowsiness, headache, memory impairment, paradoxical excitement, and anterograde amnesia, but does not affect transient global amnesia. Side effects due to rapid decrease in dose or abrupt withdrawal from oxazepam may include abdominal and muscle cramps, convulsions, depression, inability to fall asleep or stay asleep, sweating, tremors, or vomiting.