629. Ancitabine

Nomenclature

CAS number: 31698-14-3
(2R,3R,3aS,9aR)-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidine-2-methanol; 2,2′-anhydro-(1β-d-arabinofuranosyl)cytosine; 2,2′-O-cyclocytidine; O2,2′-cyclocytidine; ancytabine; anhydroara C.
C9H11N3O4; mol wt 225.20.
C 48.00%, H 4.92%, N 18.66%, O 28.42%.

Description and 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).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 10212-25-6
NSC-145668; Cyclo-C (Kohjin).
C9H11N3O4.HCl; mol wt 261.66.
C 41.31%, H 4.62%, N 16.06%, O 24.46%, Cl 13.55%.

Properties

Cryst, mp 248-250° (dec). [α]D23 21.8° (c = 2.0 in water). uv max (pH 1-7): 262, 231 nm (ε 10600, 9400).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Pyrimidine Analogs