4386. Gemcitabine

Nomenclature

CAS number: 95058-81-4
2′-Deoxy-2′,2′-difluorocytidine; 1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose; dFdC; dFdCyd; LY-188011; Gemzar (Lilly).
C9H11F2N3O4; mol wt 263.20.
C 41.07%, H 4.21%, F 14.44%, N 15.97%, O 24.32%.

Description and references

Prepn: L. W. Hertel, GB 2136425; idem, US 4808614 (1984, 1989 both to Lilly); L. W. Hertel et al., J. Org. Chem. 53, 2406 (1988); T. S. Chou et al., Synthesis 1992, 565. Antitumor activity: L. W. Hertel et al., Cancer Res. 50, 4417 (1990). Mode of action study: V. W. T. Ruiz et al., Biochem. Pharmacol. 46, 762 (1993). Clinical pharmacokinetics and toxicity: J. L. Abbruzzese et al., J. Clin. Oncol. 9, 491 (1991). Review of clinical studies: B. Lund et al., Cancer Treat. Rev. 19, 45-55 (1993).

Chemical structure

Properties

Crystals from water, pH 8.5. [α]365 +425.36°; [α]D +71.51° (c = 0.96 in methanol). uv max (ethanol): 234, 268 (ε 7810, 8560). LD10 i.v. in rats: 200 mg/m2 (Abbruzzese).

Derivative

Hydrochloride.

Nomenclature

CAS number: 122111-03-9
C9H11F2N3O4.HCl; mol wt 299.66.
C 36.07%, H 4.04%, F 12.68%, N 14.02%, O 21.36%, Cl 11.83%.

Properties

Crystals from water-acetone, mp 287-292° (dec). [α]D +48°; [α]365 +257.9° (c = 1.0 in deuterated water). uv max (water): 232, 268 nm (ε 7960, 9360).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Pyrimidine Analogs