8832. Streptozocin

Nomenclature

CAS number: 18883-66-4
2-Deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-d-glucose; 2-deoxy-2-(3-methyl-3-nitrosoureido)-d-glucopyranose; streptozotocin; NSC-85998; U-9889; Zanosar (Pharmacia & Upjohn).
C8H15N3O7; mol wt 265.22.
C 36.23%, H 5.70%, N 15.84%, O 42.23%.

Description and references

Isoln from Streptomyces achromogenes fermentation broth: Herr et al., Antibiot. Annu. 1959-1960, 236; Bergy et al., FR 1434920 (1966 to Upjohn), C.A. 65, 17661h (1966). Structure and synthesis: R. R. Herr et al., J. Am. Chem. Soc. 89, 4808 (1967); E. Hardegger et al., Helv. Chim. Acta 52, 2555 (1969); E. J. Hessler, H. K. Jahnke, J. Org. Chem. 35, 245 (1970); P. F. Wiley et al., ibid. 44, 9 (1979). Diabetogenic effect: Rakieten et al., Cancer Chemother. Rep. 29, 91 (May 1963). Antileukemic activity: Bhuyan et al., Cancer Chemother. Rep. Part 1 56, 709 (1972). Biosynthetic study: S. Singaram et al., J. Antibiot. 32, 379 (1979). Review and evaluation of studies of carcinogenicity in laboratory animals: IARC Monographs 4, 221-227 (1974). Review: B. Rudas, Arzneim.-Forsch. 22, 830-861 (1972); P. F. Wiley, Anticancer Agents Based on Natural Product Models, J. M. Cassidy, J. D. Douros, Eds. (Academic Press, New York, 1980) pp 167-200. Book: Streptozotocin: Fundamentals and Therapy, M. K. Agarwal, Ed. (Elsevier/North Holland Biomedical Press, New York, 1981) 309 pp. Review of pharmacology and clinical efficacy: R. B. Weiss et al., J. Org. Chem. 44, 9-16 (1978).

Chemical structure

Properties

Pointed platelets or prisms, from 95% ethanol, mp 115° (dec). Sol in H2O, lower alcohols and ketones. uv max (ethanol): 228 nm (ε 6360). A mixture of α and β anomers; aq solns rapidly undergo mutarotation to an equilibrium value of [α]D25 +39°. LD50 in female mice (mg/kg): 360 i.p.; 275 i.v.; in male dogs (mg/kg): 50 i.v. See: M. Iwasaki et al., J. Med. Chem. 19, 918 (1976).

Derivative

Tetraacetate.
C8H11N3O7(COCH3)4; mol wt 433.37.
C 44.34%, H 5.35%, N 9.70%, O 40.61%.

Properties

Crystals, mp 111-114° (dec). [α]D25 +41° (c = 0.78 in 95% ethanol).

Caution

Streptozocin is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-234.

Use

Production of experimental diabetes in laboratory animals.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

Antineoplastic.

Keywords

Antineoplastic; Antibiotics and Analogs