8109. Ranimustine

Nomenclature

CAS number: 58994-96-0
Methyl 6-[[[(2-chloroethyl)nitrosoamino]carbonyl]amino]-6-deoxy-α-d-glucopyranoside; methyl N-carbamyl-N′-(2-chloroethyl)-N′-nitroso-6-amino-6-deoxy-α-d-glucopyranoside; 6-[3-(2-chloroethyl)-3-nitrosoureido]-6-deoxy-α-d-glucopyranoside; 3-(methyl-α-d-glucopyranos-6-yl)-1-(2-chloroethyl)-1-nitrosourea; ranomustine; MCNU; NSC-0270516; Cymerin (Tokyo Tanabe); Thymerin (Tokyo Tanabe).
C10H18ClN3O7; mol wt 327.72.
C 36.65%, H 5.54%, Cl 10.82%, N 12.82%, O 34.17%.

Description and references

Chloroethylnitrosourea derivative with antitumor activity. Similar to carmustine, chlorozotocin, lomustine, nimustine, q.q.v. Prepn: NL 7507973; G. Kimura, J. Sekine, US 4057684; NL 7800920; G. Kimura, US 4156777 (1976, 1977, 1978, 1979, all to Tokyo Tanabe). Antitumor activity in rodents, comparison with other nitrosoureas: S. Sekido et al., Cancer Treat. Rep. 63, 961 (1979); S. Fujimoto, M. Ogawa, Cancer Chemother. Pharmacol. 9, 134 (1982); S. Fujimoto et al., Gann 75, 937 (1984). Mechanism of action: R. Kanamaru et al., Curr. Chemother. Immunother. 2, 1377 (1982). Effect of sugar alcohols on toxicity in mice: T. Tashiro et al., Cancer Chemother. Pharmacol. 8, 183 (1982). Series of articles on metabolic fate in rats: Y. Esumi et al., Iyakuhin Kenkyu 16, 381-428 (1985), C.A. 103, 115620q, 115621r, 134369f (1985). Clinical study in hematological malignant diseases: T. Masaoka et al., Chemotherapy (Tokyo) 33, 271 (1985).

Chemical structure

Properties

Pale yellowish needles from anhydrous ethanol-ethyl ether (l:1), mp 111-112°. [α]D20 +93.2° (c = 0.5 in methanol) (Kimura). Also reported as 101-103° (dec) from isopropanol. [α]D25 +73.2° (c = 0.3 in methanol) (Kimura, Sekine). Solubility in water: 900 mg/ml at 25°. LD50 in male rats (mg/kg): 42 i.p., 42 i.v., 50 orally (Kimura).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Nitrosoureas