Clobazam

Clobazam
Clinical data
Trade names	Onfi, Sympazan, Frisium, others
AHFS/Drugs.com	Monograph
MedlinePlus	a612008
License data	US DailyMed: Clobazam;
Pregnancy; category	AU: C; ;
Dependence; liability	Very high
Addiction; liability	High
Routes of; administration	By mouth, sublingual
Drug class	Benzodiazepine
ATC code	N05BA09 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Prescription only (Anlage III for higher doses); NZ: Class C; UK: Class C; US: Schedule IV; UN: Psychotropic Schedule IV; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	87% (oral)
Protein binding	80–90%
Metabolism	Liver
Metabolites	• N-desmethylclobazam (nor-Clobazam); • 4'-hydroxy-N-desmethylclobazam; • 4'-hydroxyclobazam; ;
Onset of action	0.5–4 hours
Elimination half-life	• Clobazam: 36–42 hours; • N-desmethylclobazam (nor-Clobazam): 71–82 hours;
Excretion	Kidney (82%); Feces (11%); ;
Identifiers
	IUPAC name 7-chloro-1-methyl-5-phenyl-1,5-benzodiazepine-2,4-dione;
CAS Number	22316-47-8;
PubChem CID	2789;
IUPHAR/BPS	7149;
DrugBank	DB00349;
ChemSpider	2687;
UNII	2MRO291B4U;
KEGG	D01253;
ChEBI	CHEBI:31413;
ChEMBL	ChEMBL70418;
CompTox Dashboard (EPA)	DTXSID2046759 ;
ECHA InfoCard	100.040.810
Chemical and physical data
Formula	C16H13ClN2O2
Molar mass	300.74 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC(N(C2=CC=CC=C2)C(CC(N3C)=O)=O)=C3C=C1;
	InChI InChI=1S/C16H13ClN2O2/c1-18-13-8-7-11(17)9-14(13)19(16(21)10-15(18)20)12-5-3-2-4-6-12/h2-9H,10H2,1H3; Key:CXOXHMZGEKVPMT-UHFFFAOYSA-N;

Clobazam (INN) is a long-acting benzodiazepine derivative sold under the brand names Onfi, Sympazan, Frisium among others, is used as a sedative-hypnotic, anxiolytic, and anticonvulsant that was patented in 1968. Clobazam was first synthesized in 1966 and first published in 1969. It was approved in Australia in 1970 and France in 1974 for short-term anxiety management. Marketing for clobazam in the treatment of epilepsy began in 1984. The primary drug-development goal was to provide greater anxiolytic, anti-obsessive efficacy with fewer benzodiazepine-related side effects. Clobazam is a unique 1,5-benzodiazepine which is used in the United States only as an anticonvulsant. It is available in other countries for the therapy of severe and disabling anxiety in addition to epilepsy. Clobazam has shown a distinct profile and addictive potential compared to the more common benzodiazepines.

In October 2011, the US Food and Drug Administration approved clobazam as an adjunctive treatment for seizures associated with Lennox–Gastaut syndrome in adults and children aged two years of age and older. In 2005, clobazam also received approval from Health Canada as an add-on therapy for generalized tonic–clonic, myoclonic, and focal impaired awareness seizures.