3586. Enocitabine

Nomenclature

CAS number: 55726-47-1
N-(1-β-d-Arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)docosanamide; N(4)-behenoyl-1-β-d-arabinofuranosylcytosine; behenoylcytosine arabinoside; BH-AC; NSC-239336; Sunrabin (Asahi).
C31H55N3O6; mol wt 565.78.
C 65.81%, H 9.80%, N 7.43%, O 16.97%.

Description and references

Deriv of cytarabine, q.v. Prepn: T. Ishida et al., DE 2426304; eidem, US 3991045 (1975, 1976 both to Asahi); M. Akiyama et al., Chem. Pharm. Bull. 26, 981 (1978). Antitumor activity: M. Aoshima et al., Cancer Res. 36, 2726 (1976); eidem, ibid. 37, 2481 (1977). Distribution, excretion: M. Fukama et al., Gan to Kagaku Ryoho 7, 2109 (1980), C.A. 95, 35186 (1981). Effect and mode of action: T. Kataoka, Y. Sakurai, Recent Results Cancer Res. 70, 147 (1980). Pharmacological and clinical studies: K. Yamada et al., ibid. 219.

Chemical structure

Properties

Crystals from DMSO, mp 141-142°. [α]D +70° (c = 1 in THF, 22°). uv max (isopropyl alcohol): 216, 248, 303 nm (ε 16400, 15200, 8200).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Pyrimidine Analogs