Diazepam

Diazepam, first marketed as Valium, is a medicine of the benzodiazepine family that acts as an anxiolytic. It is commonly used to treat a range of conditions, including anxiety, seizures, alcohol withdrawal syndrome, muscle spasms, insomnia, and restless legs syndrome. It may also be used to cause memory loss during certain medical procedures. It can be taken orally (by mouth), as a suppository inserted into the rectum, intramuscularly (injected into muscle), intravenously (injection into a vein) or used as a nasal spray. When injected intravenously, effects begin in one to five minutes and last up to an hour. Orally, effects begin after 15 to 60 minutes.

Diazepam
Clinical data
Pronunciation/dˈæzɪpæm/ dy-AZ-ip-am
Trade namesValium, Vazepam, Valtoco, others
AHFS/Drugs.comMonograph
MedlinePlusa682047
License data
Pregnancy
category
  • AU: C
Dependence
liability
High
Addiction
liability
Moderate
Routes of
administration
oral, intramuscular, intravenous, rectal, nasal
Drug classBenzodiazepine
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability76% (64–97%) oral, 81% (62–98%) rectal
MetabolismLiverCYP2B6 (minor route) to desmethyldiazepam, CYP2C19 (major route) to inactive metabolites, CYP3A4 (major route) to desmethyldiazepam
Elimination half-life(50 h); 20–100 h (32–200 h for main active metabolite desmethyldiazepam)
ExcretionKidney
Identifiers
  • 7-Chloro-1,3-dihydro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.476
Chemical and physical data
FormulaC16H13ClN2O
Molar mass284.74 g·mol−1
3D model (JSmol)
  • c1ccccc1C2=NCC(=O)N(C)c3ccc(Cl)cc23
  • 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?)  (verify)

Common side effects include sleepiness and trouble with coordination. Serious side effects are rare. They include increased risk of 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 works by increasing the effect of the neurotransmitter gamma-aminobutyric acid (GABA).

Diazepam was patented in 1959 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 best-selling medication between 1968 and 1982, selling more than 2 billion tablets in 1978 alone. In 2021, it was the 149th most commonly prescribed medication in the United States, with more than 3 million prescriptions. In 1985, the patent ended, and there are more than 500 brands available on the market. It is on the World Health Organization's List of Essential Medicines.

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