2073. Chlorambucil

Nomenclature

CAS number: 305-03-3
4-[Bis(2-chloroethyl)amino]benzenebutanoic acid; 4-[p-[bis(2-chloroethyl)amino]phenyl]butyric acid; γ-[p-di(2-chloroethyl)aminophenyl]butyric acid; N,N-di-2-chloroethyl-γ-p-aminophenylbutyric acid; chloraminophene; chloroambucil; CB-1348; Leukeran (GSK).
C14H19Cl2NO2; mol wt 304.21.
C 55.27%, H 6.30%, Cl 23.31%, N 4.60%, O 10.52%.

Description and 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).

Chemical structure

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 μmole/kg (Ross).

Caution

This substance is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-47.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

Antineoplastic agent, esp for leukemia.

Keywords

Antineoplastic; Alkylating Agents; Nitrogen Mustards