1614-12-6

1-Aminobenztriazole (1614-12-6) is a pan-specific cytochrome P450 inhibitor acting as a suicide substrate.1,2?Blocks omega-oxidation of arachidonic acid but not its epoxidation.3

yellow to beige or light brown crystalline powder

1-Aminobenzotriazole is used as a Suicide inhibitor of cytochrome P450 and chloroperoxidase, an inhibitor of oxidative drug metabolism in biochemical pharmacology and toxicology studies.

1-Aminobenzotriazole (1-ABT) is used as an in vitro tool in drug discovery. It can differentiate the P450 from non-P450 enzyme systems. 1-ABT exhibits inhibitory action by covalent alteration of the heme prosthetic group in the P450 enzyme.

To a solution of benzotriazole (5 g, 42.01 mmol) and potassium hydroxide (11.76 g, 0.21 mol) in water (50 mL) was added hydroxylamine-O-sulfonic acid (9.49 g, 84.02 mmol) in batches while controlling the temperature of the reaction not to exceed 50 °C. After the addition was completed, the reaction mixture was stirred at room temperature for 2 hours. The precipitate was collected by filtration and washed well with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using petroleum ether: ethyl acetate (300:1) as eluent to afford 1H-benzo[d][1,2,3]triazol-1-amine as a white solid (1.52 g, 27% yield). Mass spectrum (ESI) m/z: 135 [M + H]+.

CYP2; CYP3

1) Mugford?et al.?(1995),?1-Aminobenzotriazole-Induced Destruction of Hepatic and Renal Cytochrome P450 in Male Sprague-Dawley Rats; Fundam. Appl. Tox.,?19?43 2) Emoto?et al.?(2005),?In Vitro Inhibitory Effect of 1-Aminobenzotriazole on Drug Oxidations in Human Liver Microsomes: A Comparison With SKF-525A; Drug Metab. Pharmacokinet.,?20?351 3) Su?et al.?(1998),?Inhibition of Renal Arachidonic Acid Omega-Hydroxylase Activity With ABT Reduces Blood Pressure in the SHR; Am. J. Physiol.,?275?R426