Desmethyldiazepam

Nordazepam

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Routes of administration	Oral
ATC code	N05BA16 (WHO)
Legal status
Legal status	CA: Schedule IV DE: Anlage III (Prescription only) US: Schedule IV
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Biological half-life	36-200 hours
Excretion	Renal
Identifiers
IUPAC name 7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Synonyms	Nordiazepam, desoxydemoxepam, desmethyldiazepam
CAS Number	1088-11-5 Y
PubChem CID	2997
DrugBank	[2]  N
ChemSpider	2890 Y
UNII	67220MCM01
KEGG	D08283 Y
ChEBI	CHEBI:111762 Y
ChEMBL	CHEMBL523 Y
ECHA InfoCard	100.012.840
Chemical and physical data
Formula	C15H11ClN2O
Molar mass	270.71 g/mol
3D model (Jmol)	Interactive image
SMILES ClC1=CC2=C(C=C1)NC(CN=C2C3=CC=CC=C3)=O
InChI InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19) Y Key:AKPLHCDWDRPJGD-UHFFFAOYSA-N Y
NY (what is this?)

Nordazepam (INN; marketed under brand names Nordaz, Stilny, Madar, Vegesan, and Calmday; also known as nordiazepam, desoxydemoxepam, and desmethyldiazepam) is a 1,4-benzodiazepine derivative. Like other benzodiazepine derivatives, it has amnesic, anticonvulsant, anxiolytic, muscle relaxant, and sedative properties. However, it is used primarily in the treatment of anxiety disorders. It is an active metabolite of diazepam, chlordiazepoxide, clorazepate, prazepam, pinazepam, and medazepam.

Nordazepam is among the longest lasting (longest half-life) benzodiazepines, and its occurrence as a metabolite is responsible for most cumulative side-effects of its myriad of pro-drugs when they are used repeatedly at moderate-high doses; the nordazepam metabolite oxazepam is also active (and is a more potent, full BZD-site agonist), which contributes to nordazepam cumulative side-effects but occur too minutely to contribute to the cumulative side-effects of nordazepam pro-drugs (except when they are abused chronically in extremely supra-therapeutic doses).

Common side effects of nordazepam include somnolence, which is more common in elderly patients and/or people on high-dose regimens. Hypotonia, which is much less common, is also associated with high doses and/or old age.

Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol- or drug-dependent individuals, and individuals with comorbid psychiatric disorders. In fact, changes in liver function associated with aging or diseases such as cirrhosis, may lead to impaired clearance of nordazepam.