Title: Ancitabine
CAS Registry Number: 31698-14-3
CAS Name: [2R-(2a,3b,3ab,9ab)]-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo[2¢,3¢:4,5]oxazolo[3,2-a]pyrimidine-2-methanol
Additional Names: 2,2¢-anhydro-(1b-D-arabinofuranosyl)cytosine; 2,2¢-O-cyclocytidine; O2,2¢-cyclocytidine; ancytabine; anhydroara C
Molecular Formula: C9H11N3O4
Molecular Weight: 225.20
Percent Composition: C 48.00%, H 4.92%, N 18.66%, O 28.42%
Literature References: A cytostatic agent and intermediate in the synthesis of cytarabine, q.v. Prepn of the hydrochloride: E. R. Walwick et al., Proc. Chem. Soc. London 1959, 84; T. Y. Shen, W. V. Ruyle, US 3463850 (1969 to Merck & Co.); E. K. Hamamura et al., J. Med. Chem. 19, 654 (1976). General pharmacological properties: H. Hirayama et al., Oyo Yakuri 6, 1259 (1972), C.A. 79, 49175f (1973). Metabolism: D. H. W. Ho, Drug Metab. Dispos. 1, 752 (1973). Biochemical study: idem, Biochem. Pharmacol. 23, 1235 (1974). Pharmacokinetic study: H. S. Chen, J. F. Gross, Cancer Chemother. Pharmacol. 2, 85 (1979). Clinical studies: J. Z. Finklestein et al., Cancer Treat. Rep. 63, 1331 (1979); T. Miale et al., ibid. 1913. Toxicity studies: K. Sugihara et al., Oyo Yakuri 8, 1469 (1974); H. Hirayama et al., ibid. 1693, C.A. 83, 71766, 37747 (1975). HPLC study: V. Reichelova et al., J. Chromatogr. 588, 147 (1991).
Derivative Type: Hydrochloride
CAS Registry Number: 10212-25-6
Manufacturers' Codes: NSC-145668
Trademarks: Cyclo-C (Kohjin)
Molecular Formula: C9H11N3O4.HCl
Molecular Weight: 261.66
Percent Composition: C 41.31%, H 4.62%, N 16.06%, O 24.46%, Cl 13.55%
Properties: Cryst, mp 248-250° (dec). [a]D23 -21.8° (c = 2.0 in water). uv max (pH 1-7): 262, 231 nm (e 10600, 9400).
Melting point: mp 248-250° (dec)
Optical Rotation: [a]D23 -21.8° (c = 2.0 in water)
Absorption maximum: uv max (pH 1-7): 262, 231 nm (e 10600, 9400)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs. |