CAS No 2353-33-5 , 5-Aza-2'-deoxycytidine

Title: Decitabine
CAS Registry Number: 2353-33-5
CAS Name: 4-Amino-1-(2-deoxy-b-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one
Synonyms: 5-aza-2￠-deoxycytidine
Manufacturers' Codes: NSC-127716
Trademarks: Dacogen (SuperGen)
Molecular Formula: C8H12N4O4
Molecular Weight: 228.21
Percent Composition: C 42.10%, H 5.30%, N 24.55%, O 28.04%
Literature References: Pyrimidine analog that inhibits DNA methylation and induces differentiation of leukemic cells. Prepn: J. Pliml, F. Sorm, Collect. Czech. Chem. Commun. 29, 2576 (1964); A. Piskala, F. Sorm, in Nucleic Acid Chemistry Part 1 (Wiley, New York, 1978) pp 443-449. Improved synthesis: J. Ben-Hattar, J. Jiricny, Nucleosides Nucleotides 6, 393 (1987). Chemical stability in soln: K.-T. Lin et al., J. Pharm. Sci. 70, 1228 (1981). HPLC determn in plasma: eidem, J. Chromatogr. 345, 162 (1985). Clinical trial in chronic myelogenous leukemia: H. M. Kantarjian et al., Cancer 98, 522 (2003). Review of pharmacology and mechanism of action: R. L. Momparler, Pharmacol. Ther. 30, 287-299 (1985); idem et al., Leukemia 11, Suppl. 1, 1-6 (1997); of clinical experience: B. T. Hennessy et al., Expert. Opin. Invest. Drugs 12, 1985-1993 (2003).
Properties: Crystals from methanol, mp 201-202° (dec). [a]D22 +68.5° (30 min) ? +57.8° (6 hr) (c = 0.5 in water). uv max (pH 7): 244 nm (log e 3.86). LD50 in mice (mg/kg): 190 i.p. (Momparler, 1985).
Melting point: mp 201-202° (dec)
Optical Rotation: [a]D22 +68.5° (30 min) ? +57.8° (6 hr) (c = 0.5 in water)
Absorption maximum: uv max (pH 7): 244 nm (log e 3.86)
Toxicity data: LD50 in mice (mg/kg): 190 i.p. (Momparler, 1985)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.