Tirapazamine

Tirapazamine is a hypoxia-activated anticancer agent. It is converted to an oxidizing radical under hypoxic conditions and can induce single- and double-strand breaks in DNA, formation of trapped topoisomerase I- and II-DNA complexes, and other chromosomal aberrations, leading to cytotoxicity. Tirapazamine induces hypoxia-enhanced cytotoxicity in DT40 cells (IC50s = 1.02 and 4.34 µM in hypoxic and normoxic conditions, respectively). It also induces cytotoxicity in HT-1080 and A549 cells in a concentration-dependent manner under hypoxic conditions. In vivo, tirapazamine sensitizes tumors to cisplatin (Cay-13119) in a mouse RIF-1 fibrosarcoma tumor model. Tirapazamine (0.08 mmol/kg) also sensitizes tumors to fractionated irradiation in a FaDu hypopharyngeal squamous cell carcinoma mouse xenograft model.Formal Name: 1,2,4-benzotriazin-3-amine 1,4-dioxide. CAS Number: 27314-97-2. Synonyms: 3-Amino-1,2,4-benzotriazine 1,4-Dioxide, SR 259075, SR 4233, WIN 59075. Molecular Formula: C7H6N4O2. Formula Weight: 178.2. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMSO: Soluble. lambdamax: 223, 271 nm. SMILES: NC1=[N+]([O-])C2=CC=CC=C2[N+]([O-])=N1. InChi Code: InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9). InChi Key: ORYDPOVDJJZGHQ-UHFFFAOYSA-N.