Chlorambucil

Title: Chlorambucil
CAS Registry Number: 305-03-3
CAS Name: 4-[Bis(2-chloroethyl)amino]benzenebutanoic acid
Additional Names: 4-[p-[bis(2-chloroethyl)amino]phenyl]butyric acid; g-[p-di(2-chloroethyl)aminophenyl]butyric acid; N,N-di-2-chloroethyl-g-p-aminophenylbutyric acid; chloraminophene; chloroambucil
Manufacturers' Codes: CB-1348
Trademarks: Leukeran (GSK)
Molecular Formula: C14H19Cl2NO2
Molecular Weight: 304.21
Percent Composition: C 55.27%, H 6.30%, Cl 23.31%, N 4.60%, O 10.52%
Literature References: Nitrogen mustard deriv. Prepn: W. C. J. Ross et al., GB 727336; eidem, US 2944079 (1955, 1960 both to Nat. Res. Dev. Corp.); Everett et al., J. Chem. Soc. 1953, 2390. Improved process: Phillips, Mentha, US 3046301 (1962 to Burroughs Wellcome). Chemotherapeutic activity: Van Putten et al., Eur. J. Cancer 7, 11 (1971). Toxicity: W. C. J. Ross, Biochem. Pharmacol. 13, 969 (1964). Review of carcinogenicity studies: IARC Monographs 9, 125-134 (1975). Comprehensive description: M. Tariq, A. A. Al-Badr, Anal. Profiles Drug Subs. 16, 85-118 (1987).
Properties: Flattened needles from petr ether, mp 64-66°. Sol in ether. Sol (20°) in 1.5 parts alcohol, in 2.5 parts chloroform, in 2 parts acetone. Practically insol in water. LD50 i.p. in rats: 58.2 mmole/kg (Ross).
Melting point: mp 64-66°
Toxicity data: LD50 i.p. in rats: 58.2 mmole/kg (Ross)
CAUTION: This substance is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-47.
Therap-Cat: Antineoplastic.
Therap-Cat-Vet: Antineoplastic agent, esp for leukemia.
Keywords: Antineoplastic; Alkylating Agents; Nitrogen Mustards.
Chloramine-B Chloramine-T Chloraminophenamide Chloramphenicol Chloranil

Chlorambucil
Chlorambucil.svg
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Systematic (IUPAC) name
4-[bis(2-chlorethyl)amino]benzenebutanoic acid
Clinical data
Trade names Leukeran
AHFS/Drugs.com monograph
MedlinePlus a682899
Pregnancy cat. D (US)
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life 1.5 hours
Excretion N/A
Identifiers
CAS number 305-03-3 YesY
ATC code L01AA02
PubChem CID 2708
DrugBank DB00291
ChemSpider 2607 YesY
UNII 18D0SL7309 YesY
KEGG D00266 YesY
ChEBI CHEBI:28830 YesY
ChEMBL CHEMBL515 YesY
Chemical data
Formula C14H19Cl2NO2 
Mol. mass 304.212 g/mol
 YesY (what is this?)  (verify)

Chlorambucil (marketed as Leukeran by GlaxoSmithKline) is a chemotherapy drug that has been mainly used in the treatment of chronic lymphocytic leukemia. It is a nitrogen mustard alkylating agent[1] and can be given orally.