Flurazepam

Flurazepam
Clinical data
Trade names	Dalmane, Dalmadorm, Fluzepam
AHFS/Drugs.com	Monograph
MedlinePlus	a682051
Pregnancy; category	X (Contraindicated in pregnancy);
Addiction; liability	Moderate
Routes of; administration	By mouth
Drug class	Benzodiazepine
ATC code	N05CD01 (WHO) ;
Legal status
Legal status	BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Prescription only (Anlage III for higher doses); US: Schedule IV;
Pharmacokinetic data
Bioavailability	83%
Metabolism	Liver
Metabolites	N-desalkylflurazepam (active metabolite)
Elimination half-life	2.3 hours; N-desalkylflurazepam: 47–100 hours
Excretion	Kidney
Identifiers
	IUPAC name 7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one;
CAS Number	17617-23-1 ;
PubChem CID	3393;
IUPHAR/BPS	7188;
DrugBank	DB00690 ;
ChemSpider	3276 ;
UNII	IHP475989U;
KEGG	D00329 ;
ChEBI	CHEBI:5128;
ChEMBL	ChEMBL968 ;
PDB ligand	FL7 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1023071 ;
ECHA InfoCard	100.037.795
Chemical and physical data
Formula	C21H23ClFN3O
Molar mass	387.88 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	79.5 °C (175.1 °F)
	SMILES FC1=CC=CC=C1C2=NCC(N(CCN(CC)CC)C3=C2C=C(C=C3)Cl)=O;
	InChI InChI=1S/C21H23ClFN3O/c1-3-25(4-2)11-12-26-19-10-9-15(22)13-17(19)21(24-14-20(26)27)16-7-5-6-8-18(16)23/h5-10,13H,3-4,11-12,14H2,1-2H3 ; Key:SAADBVWGJQAEFS-UHFFFAOYSA-N ;
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Flurazepam (marketed under the brand names Dalmane and Dalmadorm) is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. It produces a metabolite with a long half-life, which may stay in the bloodstream for days. Flurazepam was patented in 1968 and came into medical use the same year. Flurazepam, developed by Roche Pharmaceuticals, was one of the first benzodiazepine hypnotic medications to be marketed.