Cisplatin

Title: Cisplatin
CAS Registry Number: 15663-27-1
CAS Name: (SP-4-2)-Diamminedichloroplatinum
Additional Names: 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.
Citiolone Citraconic Acid Citral Citramalic Acid Citrazinic Acid

Cisplatin
Cisplatin-stereo.svg
Cisplatin-3D-vdW.png
Systematic (IUPAC) name
(SP-4-2)-diamminedichloroplatinum(II)
Clinical data
Trade names Platinol
AHFS/Drugs.com monograph
MedlinePlus a684036
Pregnancy cat. D (US)
Legal status Prescription only (US)
Routes Intravenous
Pharmacokinetic data
Bioavailability complete
Protein binding > 95%
Half-life 30-100 hours
Excretion Renal
Identifiers
CAS number 15663-27-1 YesY
ATC code L01XA01
PubChem CID 84691
DrugBank DB00515
ChemSpider 21241270 YesY
UNII Q20Q21Q62J YesY
KEGG D00275 YesY
ChEBI CHEBI:27899 YesY
ChEMBL CHEMBL273943 N
Chemical data
Formula H6Cl2N2Pt 
Mol. mass 300.01 g/mol
 N (what is this?)  (verify)

Cisplatin, cisplatinum, or cis-diamminedichloroplatinum(II)[1] (CDDP) is a chemotherapy drug. It was the first member of a class of platinum-containing anti-cancer drugs, which now also includes carboplatin and oxaliplatin. These platinum complexes react in vivo, binding to and causing crosslinking of DNA, which ultimately triggers apoptosis (programmed cell death).