Chlordiazepoxide

Chlordiazepoxide

Clinical data
Pronunciation	/ˌklɔərdaɪ.əzᵻˈpɒksaɪd/
Trade names	Librium
AHFS/Drugs.com	Monograph
MedlinePlus	a682078
Pregnancy category	US: D (Evidence of risk)
Routes of administration	oral intramuscular
ATC code	N05BA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV DE: Anlage III (Prescription only) UK: Class C US: Schedule IV
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	5–30 hours (Active metabolite desmethyldiazepam 36–200 hours: other active metabolites include oxazepam)
Excretion	Renal
Identifiers
IUPAC name 7-chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide
CAS Number	58-25-3 Y
PubChem CID	2712
IUPHAR/BPS	3370
DrugBank	DB00475 Y
ChemSpider	10248513 Y
UNII	6RZ6XEZ3CR
KEGG	D00267 Y
ChEBI	CHEBI:3611 Y
ChEMBL	CHEMBL451 Y
ECHA InfoCard	100.000.337
Chemical and physical data
Formula	C16H14ClN3O
Molar mass	299.75 g/mol
3D model (Jmol)	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) Y Key:ANTSCNMPPGJYLG-UHFFFAOYSA-N Y

Chlordiazepoxide, trade name Librium, is a sedative and hypnotic medication of the benzodiazepine class.

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

Chlordiazepoxide was discovered in 1959. 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.

Chlordiazepoxide is indicated for the short-term (2–4 weeks) treatment of anxiety that is severe and disabling or subjecting the person to unacceptable distress. It is also indicated as a treatment for the management of acute alcohol withdrawal syndrome. When combined with Amitriptyline (known as Limbitrol), it can be used to treat new daily persistent headache disorder.

Use of chlordiazepoxide should be avoided in individuals with the following conditions:

Chlordiazepoxide is generally considered an inappropriate benzodiazepine for the elderly due to its long elimination half-life and the risks of accumulation. Benzodiazepines require special precaution if used in the elderly, pregnancy, children, alcohol- or drug-dependent individuals and individuals with comorbid psychiatric disorders.

The research into the safety of benzodiazepines during pregnancy is limited and it is recommended that use of benzodiazepines during pregnancy should be based on whether the benefits outweigh the risks. If chlordiazepoxide is used during pregnancy the risks can be reduced via using the lowest effective dose and for the shortest time possible. Benzodiazepines should generally be avoided during the first trimester of pregnancy. Chlordiazepoxide and diazepam are considered to be among the safer benzodiazepines to use during pregnancy in comparison to other benzodiazepines. Possible adverse effects from benzodiazepine use during pregnancy include, abortion, malformation, intrauterine growth retardation, functional deficits, carcinogenesis and mutagenesis. Caution is also advised during breast feeding as chlordiazepoxide passes into breast milk.