Tirapazamine
Title: Tirapazamine
CAS Registry Number: 27314-97-2
CAS Name: 1,2,4-Benzotriazin-3-amine 1,4-dioxide
Additional Names: 3-amino-1,2,4-benzotriazine 1,4-dioxide
Manufacturers' Codes: NSC-130181; SR-4233; Win-59075
Trademarks: Tirazone (Sanofi Winthrop)
Molecular Formula: C7H6N4O2
Molecular Weight: 178.15
Percent Composition: C 47.19%, H 3.39%, N 31.45%, O 17.96%
Literature References: Bioreductive anticancer agent; selectively toxic to cells under hypoxic conditions. Prepn: R. F. Robbins, K. Schofield, J. Chem. Soc. 1957, 3186; J. C. Mason, G. Tennant, J. Chem. Soc. B 1970, 911. See also: K. Ley et al., DE 2204574; eidem, US 3868371 (1973, 1975 both to Bayer). HPLC determn in plasma: H. Robin, Jr. et al., Cancer Chemother. Pharmacol. 36, 266 (1995). Review of pharmacology and mechanism of action studies: J. M. Brown, Br. J. Cancer 67, 1163-1170 (1993). Clinical evaluation in combination with cisplatin: C. A. Johnson et al., J. Clin. Oncol. 15, 773 (1997).
Properties: Orange needles from methanol, mp 229-230° (dec) (Robbins, Scholfield). Also reported as reddish-golden crystals from water + acetic acid, mp 220° (dec) (Ley). uv max: 272, 474 nm (log e 4.24, 3.52).
Melting point: mp 229-230° (dec) (Robbins, Scholfield); mp 220° (dec) (Ley)
Absorption maximum: uv max: 272, 474 nm (log e 4.24, 3.52)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic.

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