9425. Tiazofurin

Nomenclature

CAS number: 60084-10-8
2β-d-Ribofuranosyl-4-thiazolecarboxamide; riboxamide; TCAR; CI-909; NSC-286193; Tiazole (ICN).
C9H12N2O5S; mol wt 260.27.
C 41.53%, H 4.65%, N 10.76%, O 30.74%, S 12.32%.

Description and references

Nucleoside analog that inhibits inosine monophosphate dehydrogenase (IMPDH). Prepn: M. Fuertes et al., J. Org. Chem. 41, 4074 (1976); and antiviral activity: P. C. Srivastava et al., J. Med. Chem. 20, 256 (1977). Structure-activity study: G. Gebeyehu et al., ibid. 28, 99 (1985). HPLC determn in plasma: R. W. Klecker, Jr., J. M. Collins, J. Chromatogr. 307, 361 (1984). Clinical pharmacokinetics: D. Raghavan et al., Cancer Chemother. Pharmacol. 16, 160 (1986). Clinical evaluation in leukemia: G. Tricot et al, Int. J. Cell Cloning 8, 161 (1990). Series of articles on pharmacology and clinical experience: Anticancer Res. 16, 3307-3354 (1996).

Chemical structure

Properties

Crystals from ethanol-ethyl acetate, mp 145-146°. [α]D25 9° (c = 0.5 in ethanol). uv max in ethanol: 215, 237 nm (ε 9450, 7625).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Purine Analogs; IMPDH Inhibitor