Title: Cisplatin
CAS Registry Number: 15663-27-1
CAS Name: (
SP-4-2)-Diamminedichloroplatinum
Synonyms: cis-diamminedichloroplatinum;
cis-platinum II;
cis-DDP; CACP; CPDC; DDP
Manufacturers' Codes: NSC-119875
Trademarks: Briplatin (BMS); Cismaplat (Mack, Illert.); Cisplatyl (Bellon); Citoplatino (Rh>e-Poulenc); Lederplatin (Lederle); Neoplatin (BMS); Platamine (Montedison); Platinex (BMS); Platiblastin (Farmitalia); Platinol (BMS); Platinoxan (Degussa); Platistin (Farmitalia); Platosin (Pharmachemie); Randa (Nippon Kayaku)
Molecular Formula: Cl2H6N2Pt
Molecular Weight: 300.05
Percent Composition: Cl 23.63%, H 2.02%, N 9.34%, Pt 65.02%
Literature References: 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). Originally known as
Peyrone's salt or
Peyrone's chloride, it was primarily of interest in the development of coordination theory. 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). Mechanism of action: J. J. Roberts, J. M. Pascoe,
Nature 235, 282 (1972); A. Khan, J. M. Hill,
Transplant 13, 55 (1972); G. L. Cohen
et al., Science 203, 1014 (1979). 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). Cisplatin has been shown to have trypanocidal effects: M. S. Wysor
et al., Science 217, 454 (1982). 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).
Reviews: D. D. Von Hoff, M. Rozencweig in
Advances in Pharmacology and Chemotherapy vol. 16, S. Garattini
et al., Eds. (Academic Press, New York, 1979) pp 273-294; S. J. Lippard,
Science 218, 1075-1082 (1982). 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.
Properties: Deep yellow solid, dec 270°. 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).
Toxicity data: 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.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Platinum Complexes.
