Title: Tegafur
CAS Registry Number: 17902-23-7
CAS Name: 5-Fluoro-1-(tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione
Additional Names: 5-fluoro-1-(tetrahydro-2-furyl)uracil; N1-(2¢-furanidyl)-5-fluorouracil
Manufacturers' Codes: FT-207; MJF-12264; NSC-148958
Trademarks: Citofur (Lusofarmaco); Coparogin (Nippon Chemiphar); Exonal (Toyama); Fental (Kanebo); Franrose (Hishiyama); Ftorafur (Grñenthal); Fulaid (Takeda); Fulfeel (Kyorin); Furafluor (Green Cross); Furofutran (Taiyo); Futraful (Taiho); Lamar (Tokyo Tanabe); Lifril (Kissei); Neberk (Morishita); Nitobanil (Kyowa Yakuhin); Riol (Toa Eiyo); Sinoflurol (Kaken); Sunfural (Asahi Kasei); Tefsiel C (Towa Yakuhin)
Molecular Formula: C8H9FN2O3
Molecular Weight: 200.17
Percent Composition: C 48.00%, H 4.53%, F 9.49%, N 13.99%, O 23.98%
Literature References: Prepn: S. A. Hillers et al., Dokl. Akad. Nauk SSSR 176, 332 (1967), C.A. 68, 29664j (1968); eidem, GB 1168391 (1969), C.A. 72, 43715r (1970) and FR 1574684 (1969), C.A. 73, 77281g (1970). Alternate synthesis: T. Kametani et al., J. Heterocycl. Chem. 14, 473 (1977). Synthesis, antitumor activity, toxicity study: M. Yasumoto et al., J. Med. Chem. 21, 738 (1978). Crystal structure: Y. Nakai, Chem. Pharm. Bull. 30, 2629 (1982). Pharmacokinetics, metabolism in man: J. L. Au et al., Cancer Treat. Rep. 63, 343 (1979). Evaluation of efficacy and toxicity: C. R. Smart et al., Cancer 36, 103 (1975). Evaluation in colorectal cancer: T. Buroker et al., Cancer 44, 48 (1979). In vivo and in vitro studies on Walker carcinoma in rats: J. Mattern et al., Arzneim.-Forsch. 30, 981 (1980).
Properties: Crystals from ethanol, mp 164-165°. uv max: 270 nm [e 8460 (pH 2); e 8050 (pH 7); e 6700 (pH 12)]. Easily sol in hot water, alcohol, DMF. Practically insol in ether. LD50 in mice (mg/kg): 900 orally (3 days) (Yasumoto); 750 i.p. (FR 1574684), also reported as 1150 i.p. (Smart).
Melting point: mp 164-165°
Absorption maximum: uv max: 270 nm [e 8460 (pH 2); e 8050 (pH 7); e 6700 (pH 12)]
Toxicity data: LD50 in mice (mg/kg): 900 orally (3 days) (Yasumoto); 750 i.p. (FR 1574684), also reported as 1150 i.p. (Smart)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs. |