2317. Cisplatin

Nomenclature

CAS number: 15663-27-1
(SP-4-2)-Diamminedichloroplatinum; cis-diamminedichloroplatinum; cis-platinum II; cis-DDP; CACP; CPDC; DDP; NSC-119875; Blastolem (Lemery); Briplatin (BMS); Cisplatyl (Sanofi-Aventis); Neoplatin (BMS); Platamine (Pfizer); Platinex (BMS); Platiblastin (Pfizer); Platinol (BMS); Platosin (Pharmachemie); Randa (Nippon Kayaku).
Cl2H6N2Pt; mol wt 300.05.
Cl 23.63%, H 2.02%, N 9.34%, Pt 65.02%.

Description and references

Antitumor platinum coordination complex. Originally known as Peyrone's salt or Peyrone's chloride; of interest in the development of coordination theory. Prepn: M. Peyrone, Ann. 51, 1 (1845); G. B. Kauffman, D. O. Cowan, Inorg. Synth. 7, 239 (1963); S. C. Dhara, Indian J. Chem. 8, 193 (1970). Early structural studies: R. Werner, Z. Anorg. Chem. 3, 267 (1893); H. D. K. Drew et al., J. Chem. Soc. 1932, 988. Discovery of anti-tumor activity: B. Rosenberg et al., Nature 205, 698 (1965); 222, 385 (1972). Use as neoplasm inhibitor: M. L. Tobe et al., DE 2318020 (1972 to Rustenburg Platinum Mines Ltd.), C.A. 80, 55897e (1974); M. J. Cleare et al., DE 2329485 (1972 to Research Corp.), C.A. 81, 21172v (1974). X-ray structure of cisplatin-DNA adduct: S. E. Sherman et al., Science 230, 412 (1985). Inhibition of in vitro DNA synthesis: A. L. Pinto, S. J. Lippard, Proc. Natl. Acad. Sci. USA 82, 4616 (1985). Pharmacology: A. Sirica et al., Proc. Am. Assoc. Cancer Res. 12, 4 (1971); C. L. Litterst et al., Cancer Res. 36, 2340 (1976); N. P. Johnson et al., Chem. Biol. Interact. 23, 267 (1978). Metabolism: R. C. Lange et al., J. Nucl. Med. 14, 191 (1973). Clinical studies: J. J. Ochs et al., Cancer Treat. Rep. 62, 239 (1978); H. M. Pinedo et al., Eur. J. Cancer 14, 1149 (1978). Toxicology: R. L. Dixon, Proc. 7th Int. Congr. Chemother. Vol. 2 (University Park Press, Baltimore, 1972) pp 241-243; R. W. Fleishman et al., Toxicol. Appl. Pharmacol. 33, 320 (1975). Review of carcinogenicity studies: IARC Monographs 26, 154-161 (1981); of neurotoxicity: R. J. Cersosimo, Cancer Treat. Rev. 16, 195-211 (1989). Comprehensive description: C. M. Riley, L. M. Sternson, Anal. Profiles Drug Subs. 14, 77-105 (1985). Book: Cisplatin, Current Status and New Developments, A. W. Prestayko et al., Eds. (Academic Press, New York, 1980) 527 pp. Review of mechanism of action: M. A. Fuertes et al., Curr. Med. Chem. 10, 257-266 (2003); Z. H. Siddik, Oncogene 22, 7265-7279 (2003).

Chemical structure

Properties

Yellow to orange crystalline powder. Soly in water 0.253 g/100 g at 25°; slowly changes to trans-form in aq soln. Insol in most common solvents. Sol in DMF. LD50 in guinea pigs: 9.7 mg/kg i.p. (Fleishman).

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-67.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

Antineoplastic.

Keywords

Antineoplastic; Platinum Complexes