Chlordiazepoxide

Chlordiazepoxide
Clinical data
Pronunciation	/ˌklɔːrdaɪ.əzɪˈpɒksaɪd/
Trade names	Librium
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	• Desmethyldiazepam; Desmethylchlordiazepoxide; • Demoxepam; • 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 hydrochloride, sold under the brand name Librium 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. It is also used to discontinue long term use of other, shorter acting benzodiazepines due to its long half-life.

Chlordiazepoxide has a medium to long half-life, while 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 (1978). "Clinical Pharmacokinetics of Chlordiazepoxide". Clinical Pharmacokinetics. 3 (5): 381–394. 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 (1978). "Clinical Pharmacokinetics of Chlordiazepoxide". Clinical Pharmacokinetics. 3 (5): 381–394. 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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