Valium

Diazepam

Clinical data
Pronunciation	/daɪˈæzᵻpæm/
Trade names	Valium and many others
AHFS/Drugs.com	Monograph
MedlinePlus	a682047
License data	US FDA: Diazepam
Pregnancy category	AU: C US: D (Evidence of risk)
Dependence liability	Moderate
Addiction liability	Moderate
Routes of administration	by mouth, IM, IV, suppository
ATC code	N05BA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV DE: Anlage III (Prescription only) NZ: Class C UK: Class C US: Schedule IV UN: Psychotropic Schedule IV ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	93–100%
Metabolism	Liver—CYP2B6 (minor route) to desmethyldiazepam, CYP2C19 (major route) to inactive metabolites, CYP3A4 (major route) to desmethyldiazepam
Biological half-life	20–100 hours (36–200 hours for main active metabolite desmethyldiazepam)
Excretion	Kidney
Identifiers
IUPAC name 7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
CAS Number	439-14-5 Y
PubChem CID	3016
IUPHAR/BPS	3364
DrugBank	DB00829 N
ChemSpider	2908 Y
UNII	Q3JTX2Q7TU
KEGG	D00293 Y
ChEBI	CHEBI:49575 Y
ChEMBL	CHEMBL12 Y
ECHA InfoCard	100.006.476
Chemical and physical data
Formula	C16H13ClN2O
Molar mass	284.7 g/mol
3D model (Jmol)	Interactive image
SMILES CN1C2=C(C(C3=CC=CC=C3)=NCC1=O)C=C(Cl)C=C2
InChI InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3 Y Key:AAOVKJBEBIDNHE-UHFFFAOYSA-N Y
NY (what is this?)

Diazepam, first marketed as Valium, is a medication of the benzodiazepine family that typically produces a calming effect. It is commonly used to treat a range of conditions including anxiety, alcohol withdrawal syndrome, benzodiazepine withdrawal syndrome, muscle spasms, seizures, trouble sleeping, and restless legs syndrome. It may also be used to cause memory loss during certain medical procedures. It can be taken by mouth, inserted into the rectum, injected into muscle, or injected into a vein. When given into a vein, effects begin in one to five minutes and last up to an hour. By mouth, effects may take 40 minutes to begin.

Common side effects include sleepiness and trouble with coordination. Serious side effects are rare. They include suicide, decreased breathing, and an increased risk of seizures if used too frequently in those with epilepsy. Occasionally excitement or agitation may occur.Long term use can result in tolerance, dependence, and withdrawal symptoms on dose reduction. Abrupt stopping after long-term use can be potentially dangerous. After stopping, cognitive problems may persist for six months or longer. It is not recommended during pregnancy or breastfeeding. Its mechanism of action is by increasing the effect of the neurotransmitter gamma-Aminobutyric acid (GABA).

Diazepam was first synthesized by Leo Sternbach, and was first manufactured by Hoffmann-La Roche. It has been one of the most frequently prescribed medications in the world since its launch in 1963. In the United States it was the highest selling medication between 1968 and 1982, selling more than two billion tablets in 1978 alone. In 1985 the patent ended, and there are now more than 500 brands available on the market. Diazepam is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.01 USD per dose as of 2014. In the United States it is about 0.40 USD per dose.