Chlordiazepoxide

Chlordiazepoxide, trade name Librium among others, is a sedative and hypnotic medication of the benzodiazepine class; it is used to treat anxiety, insomnia and symptoms of withdrawal from alcohol and other drugs.

Chlordiazepoxide
Clinical data
Pronunciation/ˌklɔːrdaɪ.əzɪˈpɒksaɪd/
Trade namesLibrium, others
AHFS/Drugs.comMonograph
MedlinePlusa682078
Dependence
liability		High
Routes of
administration		By mouth
intramuscular
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life5–30 hours (Active metabolite desmethyldiazepam 36–200 hours: other active metabolites include oxazepam)
ExcretionKidney
Identifiers
  • 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.337
Chemical and physical data
FormulaC16H14ClN3O
Molar mass299.76 g·mol−1
3D model (JSmol)
  • ClC1=CC2=C(N=C(NC)C[N+]([O-])=C2C3=CC=CC=C3)C=C1
  • InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9H,10H2,1H3,(H,18,19) Y
  • Key:ANTSCNMPPGJYLG-UHFFFAOYSA-N Y
  (verify)

Chlordiazepoxide has a medium to long half-life but its active metabolite has a very long half-life. The drug has amnesic, anticonvulsant, anxiolytic, hypnotic, sedative and skeletal muscle relaxant properties.

Chlordiazepoxide was patented in 1958 and approved for medical use in 1960. It was the first benzodiazepine to be synthesized and the discovery of chlordiazepoxide was by pure chance. Chlordiazepoxide and other benzodiazepines were initially accepted with widespread public approval but were followed with widespread public disapproval and recommendations for more restrictive medical guidelines for its use.

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