1754. Capecitabine

Nomenclature

CAS number: 154361-50-9
5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine; [1-(5-deoxy-β-d-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl]carbamic acid pentyl ester; pentyl 1-(5-deoxy-β-d-ribofuranosyl)-5-fluoro-1,2-dihyro-2-oxo-4-pyrimidinecarbamate; Ro-9-1978; Xeloda (Roche).
C15H22FN3O6; mol wt 359.35.
C 50.14%, H 6.17%, F 5.29%, N 11.69%, O 26.71%.

Description and references

Orally active fluoropyrimidine. Prodrug of doxifluridine, q.v., designed to be metabolized to 5-fluorouracil, q.v., at the tumor site. Prepn: M. Arasaki et al., EP 602454; eidem, US 5472949 (1994, 1995 both to Hoffmann-La Roche). Metabolism by tumor enzymes: T. Ishikawa et al., Cancer Res. 58, 685 (1998). Clinical comparison with i.v. fluorouracil in colorectal cancer: P. M. Hoff et al., J. Clin. Oncol. 19, 2282 (2001); E. Van Cutsem et al., ibid. 4097. Review of pharmacology and clinical experience: J. McKendrick, J. Coutsouvelis, Expert Opin. Pharmacother. 6, 1231-1239 (2005).

Chemical structure

Properties

Crystals from ethyl acetate, mp 110-121°. Soly in water (20°): 26 mg/ml.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Pyrimidine Analogs