Chlordiazepoxide

Chlordiazepoxide
Clinical data
Pronunciation	/ˌklɔːrdaɪ.əzɪˈpɒksaɪd/
Trade names	Librium, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682078
Dependence; liability	High
Addiction; liability	Moderate
Routes of; administration	By mouth ; intramuscular
Drug class	Benzodiazepine
ATC code	N05BA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Prescription only (Anlage III for higher doses); UK: Class C; US: Schedule IV;
Pharmacokinetic data
Metabolism	Liver
Metabolites	• Desmethylchlordiazepoxide; • Demoxepam; • Nordazepam; • Oxazepam
Elimination half-life	5–30 hours (Active metabolite desmethyldiazepam 36–200 hours: other active metabolites include oxazepam)
Excretion	Kidney
Identifiers
	IUPAC name 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide;
CAS Number	58-25-3 ;
PubChem CID	2712;
IUPHAR/BPS	3370;
DrugBank	DB00475 ;
ChemSpider	10248513 ;
UNII	6RZ6XEZ3CR;
KEGG	D00267 ;
ChEBI	CHEBI:3611 ;
ChEMBL	ChEMBL451 ;
CompTox Dashboard (EPA)	DTXSID4046022 ;
ECHA InfoCard	100.000.337
Chemical and physical data
Formula	C16H14ClN3O
Molar mass	299.76 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC2=C(N=C(NC)C[N+]([O-])=C2C3=CC=CC=C3)C=C1;
	InChI 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) ; Key:ANTSCNMPPGJYLG-UHFFFAOYSA-N ;
	(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 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]

^ Edmunds M, Mayhew M (2013). Pharmacology for the Primary Care Provider (4th ed.). Mosby. p. 545. ISBN 9780323087902.
^ 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.
^ 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. }}
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 535. ISBN 9783527607495.
^ 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.
^ 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.

[Edmunds-2013-1] 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.

[Fis2006-5] 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.

[Marshall-2009-7] 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.

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