1845. Carmustine
Nomenclature
CAS number: 154-93-8
N,N′-Bis(2-chloroethyl)-N-nitrosourea; BCNU; NSC-409962; Becenun (BMS); Bicnu (BMS); Carmubris (BMS). C5H9Cl2N3O2; mol wt 214.05.
C 28.06%, H 4.24%, Cl 33.13%, N 19.63%, O 14.95%.
Description and references
Chloroethylnitrosourea derivative with antitumor activity. Similar to chlorozotocin, lomustine, nimustine, ranimustine, q.q.v. Synthesis: Johnston et al., J. Med. Chem. 6, 669 (1963). Properties: Loo et al., J. Pharm. Sci. 55, 492 (1966). Decompn studies as related to antileukemic activity: Montgomery et al., J. Med. Chem. 10, 668 (1967). Antifungal action: Hunt, Pittilo, Antimicrob. Agents Chemother. 1965, 710. Toxicology studies: Thompson, Larson, Toxicol. Appl. Pharmacol. 21, 405 (1972). Review of pulmonary toxicity: A. C. Smith, Pharmacol. Ther. 41, 443-460 (1989).
Properties
Light yellow powder that melts to an oily liquid; mp 30-32°. Both powder and liquid are stable. Dec rapidly in acid and in soln above pH 7. Most stable in petroleum ether or aqueous soln at pH 4. Non-ionized at pH 7 with consequent high lipid solubility. Sol in water up to 4 mg/ml and in 50% ethanol up to 150 mg/ml: DeVita et al., Cancer Res. 25, 1876 (1965). LD50 in mice (mg/kg): 19-25 orally, 26 i.p., 24 s.c.; in rats (mg/kg): 30-34 orally (Thompson, Larson).Caution
This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-53.Therapeutic Category
Antineoplastic.
Keywords
Antineoplastic; Alkylating Agents; Nitrosoureas