Chlordiazepoxide

Chlordiazepoxide
Clinical data
Pronunciation/ˌklɔːrdaɪ.əzɪˈpɒksaɪd/
Trade namesLibrium, others
AHFS/Drugs.comMonograph
MedlinePlusa682078
Dependence
liability		High[1]
Addiction
liability		Moderate
Routes of
administration		By mouth
intramuscular
Drug classBenzodiazepine
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Metabolites• Desmethylchlordiazepoxide
• Demoxepam
• Nordazepam
• Oxazepam[3]
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 Edit this at Wikidata
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) checkY
  • Key:ANTSCNMPPGJYLG-UHFFFAOYSA-N checkY
  (verify)

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, benzodiazepines, and other drugs.

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.[4]

Chlordiazepoxide was patented in 1958 and approved for medical use in 1960.[5] It was the first benzodiazepine to be synthesized and the discovery of chlordiazepoxide was by pure chance.[6] 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.[7]

  1. ^ Edmunds M, Mayhew M (2013). Pharmacology for the Primary Care Provider (4th ed.). Mosby. p. 545. ISBN 9780323087902.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ Greenblatt DJ, Shader RI, MacLeod SM, Sellers EM. Clinical pharmacokinetics of chlordiazepoxide. Clin Pharmacokinet. 1978 Sep-Oct;3(5):381-94. {{doi: 10.2165/00003088-197803050-00004. PMID: 359214. }}
  4. ^ Liljequist R, Palva E, Linnoila M (1979). "Effects on learning and memory of 2-week treatments with chlordiazepoxide lactam, N-desmethyldiazepam, oxazepam and methyloxazepam, alone or in combination with alcohol". International Pharmacopsychiatry. 14 (4): 190–8. doi:10.1159/000468381. PMID 42628.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 535. ISBN 9783527607495.
  6. ^ Ban TA (2006). "The role of serendipity in drug discovery". Dialogues in Clinical Neuroscience. 8 (3): 335–44. doi:10.31887/DCNS.2006.8.3/tban. PMC 3181823. PMID 17117615.
  7. ^ Marshall KP, Georgievskava Z, Georgievsky I (June 2009). "Social reactions to Valium and Prozac: a cultural lag perspective of drug diffusion and adoption". Research in Social & Administrative Pharmacy. 5 (2): 94–107. doi:10.1016/j.sapharm.2008.06.005. PMID 19524858.