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Chemical Compound Review

Lopac-A-3940     benzotriazol-1-amine

Synonyms: PubChem19954, SureCN94751, CHEMBL101168, ACMC-1BVFA, AG-B-83478, ...
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Disease relevance of benzotriazol-1-amine


High impact information on benzotriazol-1-amine


Chemical compound and disease context of benzotriazol-1-amine

  • Both BEAS-2B cells and rabbit Clara cells were highly susceptible to DDD toxicity and were partially protected by 1-aminobenzotriazole, a suicide substrate inhibitor of cytochrome P450 enzymes [7].

Biological context of benzotriazol-1-amine


Anatomical context of benzotriazol-1-amine


Associations of benzotriazol-1-amine with other chemical compounds


Gene context of benzotriazol-1-amine

  • Because the lack of CYP2E1 did not completely inhibit urethane metabolism, the disposition of 10 mg/kg urethane was compared in mice pretreated with the P450 inhibitor, 1-aminobenzotriazole or the esterase inhibitor, paraoxon [20].
  • Parallel control and treated groups, excluding Cyp2e1-null mice, also received an i.p. injection (150 mg/kg) of the irreversible cytochrome P450 inhibitor 1-aminobenzotriazole (ABT) twice on the day before exposures began and 1 h before every exposure [22].
  • At higher substrate and protein concentration, NADPH-dependent oxidation of 5-nitroso-BP to 5-nitro-BP primarily occurred in microsomes and was completely inhibited by 1-aminobenzotriazole (1 mM), a P450 inhibitor [23].
  • This activity was not inhibited by the P450 inhibitor 1-aminobenzotriazole but was dramatically reduced following mild heat treatment [24].
  • 1-Aminobenzotriazole (ABT) is widely used as a non-specific inhibitor of animal cytochrome P450 (CYP) [25].

Analytical, diagnostic and therapeutic context of benzotriazol-1-amine


  1. In vivo inhibition of oxidative drug metabolism by, and acute toxicity of, 1-aminobenzotriazole (ABT). A tool for biochemical toxicology. Mico, B.A., Federowicz, D.A., Ripple, M.G., Kerns, W. Biochem. Pharmacol. (1988) [Pubmed]
  2. Inhibitors of cytochrome P-450 attenuate the myogenic response of dog renal arcuate arteries. Kauser, K., Clark, J.E., Masters, B.S., Ortiz de Montellano, P.R., Ma, Y.H., Harder, D.R., Roman, R.J. Circ. Res. (1991) [Pubmed]
  3. Cytochrome P450 CYP2E1, but not nicotinamide adenine dinucleotide phosphate oxidase, is required for ethanol-induced oxidative DNA damage in rodent liver. Bradford, B.U., Kono, H., Isayama, F., Kosyk, O., Wheeler, M.D., Akiyama, T.E., Bleye, L., Krausz, K.W., Gonzalez, F.J., Koop, D.R., Rusyn, I. Hepatology (2005) [Pubmed]
  4. Cooxidation of cyclophosphamide as an alternative pathway for its bioactivation and lung toxicity. Smith, R.D., Kehrer, J.P. Cancer Res. (1991) [Pubmed]
  5. The catalytic site of cytochrome P4504A11 (CYP4A11) and its L131F mutant. Dierks, E.A., Zhang, Z., Johnson, E.F., de Montellano, P.R. J. Biol. Chem. (1998) [Pubmed]
  6. Characterization of inducible nitric-oxide synthase by cytochrome P-450 substrates and inhibitors. Inhibition by chlorzoxazone. Grant, S.K., Green, B.G., Wang, R., Pacholok, S.G., Kozarich, J.W. J. Biol. Chem. (1997) [Pubmed]
  7. Oxidation at C-1 controls the cytotoxicity of 1,1-dichloro-2,2- bis(p-chlorophenyl)ethane by rabbit and human lung cells. Nichols, W.K., Terry, C.M., Cutler, N.S., Appleton, M.L., Jesthi, P.K., Yost, G.S. Drug Metab. Dispos. (1995) [Pubmed]
  8. The CYP inhibitor 1-aminobenzotriazole does not prevent oxidative stress associated with alcohol-induced liver injury in rats and mice. Isayama, F., Froh, M., Bradford, B.U., McKim, S.E., Kadiiska, M.B., Connor, H.D., Mason, R.P., Koop, D.R., Wheeler, M.D., Arteel, G.E. Free Radic. Biol. Med. (2003) [Pubmed]
  9. Attenuation of endogenous oxidative stress-induced cell death by cytochrome P450 inhibitors in primary cultures of rat hepatocytes. Shiba, D., Shimamoto, N. Free Radic. Biol. Med. (1999) [Pubmed]
  10. Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. Dubey, R.K., Jackson, E.K., Gillespie, D.G., Rosselli, M., Barchiesi, F., Krust, A., Keller, H., Zacharia, L.C., Imthurn, B. J. Clin. Endocrinol. Metab. (2005) [Pubmed]
  11. Glu-320 and Asp-323 are determinants of the CYP4A1 hydroxylation regiospecificity and resistance to inactivation by 1-aminobenzotriazole. Dierks, E.A., Davis, S.C., Ortiz de Montellano, P.R. Biochemistry (1998) [Pubmed]
  12. Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Ortiz de Montellano, P.R., Mathews, J.M. Biochem. J. (1981) [Pubmed]
  13. Induction of peroxisomal fatty acid beta-oxidation and liver fatty acid-binding protein by peroxisome proliferators. Mediation via the cytochrome P-450IVA1 omega-hydroxylase pathway. Kaikaus, R.M., Chan, W.K., Lysenko, N., Ray, R., Ortiz de Montellano, P.R., Bass, N.M. J. Biol. Chem. (1993) [Pubmed]
  14. Activation of T cells by carbamazepine and carbamazepine metabolites. Wu, Y., Sanderson, J.P., Farrell, J., Drummond, N.S., Hanson, A., Bowkett, E., Berry, N., Stachulski, A.V., Clarke, S.E., Pichler, W.J., Pirmohamed, M., Park, B.K., Naisbitt, D.J. J. Allergy Clin. Immunol. (2006) [Pubmed]
  15. Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth. Nieves, D., Moreno, J.J. J. Lipid Res. (2006) [Pubmed]
  16. Inactivation of rabbit pulmonary cytochrome P-450 in microsomes and isolated perfused lungs by the suicide substrate 1-aminobenzotriazole. Mathews, J.M., Dostal, L.A., Bend, J.R. J. Pharmacol. Exp. Ther. (1985) [Pubmed]
  17. Sulfoxidation of cysteine and mercapturic acid conjugates of the sevoflurane degradation product fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether (compound A). Altuntas, T.G., Park, S.B., Kharasch, E.D. Chem. Res. Toxicol. (2004) [Pubmed]
  18. Nitric oxide/cytochrome P450 interactions in cyclosporin A-induced effects in the rat. Blanton, A., Nsaif, R., Hercule, H., Oyekan, A. J. Hypertens. (2006) [Pubmed]
  19. Cytochrome P-450 metabolite of arachidonic acid mediates bradykinin-induced negative inotropic effect. Rastaldo, R., Paolocci, N., Chiribiri, A., Penna, C., Gattullo, D., Pagliaro, P. Am. J. Physiol. Heart Circ. Physiol. (2001) [Pubmed]
  20. Cytochrome P450 2E1 (CYP2E1) is the principal enzyme responsible for urethane metabolism: comparative studies using CYP2E1-null and wild-type mice. Hoffler, U., El-Masri, H.A., Ghanayem, B.I. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  21. Metabolism of the cytochrome P450 mechanism-based inhibitor N-benzyl-1-aminobenzotriazole to products that covalently bind with protein in guinea pig liver and lung microsomes: comparative study with 1-aminobenzotriazole. Woodcroft, K.J., Webb, C.D., Yao, M., Weedon, A.C., Bend, J.R. Chem. Res. Toxicol. (1997) [Pubmed]
  22. Metabolism of chloroform by cytochrome P450 2E1 is required for induction of toxicity in the liver, kidney, and nose of male mice. Constan, A.A., Sprankle, C.S., Peters, J.M., Kedderis, G.L., Everitt, J.I., Wong, B.A., Gonzalez, F.L., Butterworth, B.E. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
  23. Pharmacokinetics and metabolism in rats of 2,4-diamino-6-benzyloxy-5- nitrosopyrimidine, an inactivator of O6-alkylguanine-DNA alkyltransferase. Roy, S.K., Moschel, R.C., Dolan, M.E. Drug Metab. Dispos. (1996) [Pubmed]
  24. Extrahepatic metabolism of carbamate and organophosphate thioether compounds by the flavin-containing monooxygenase and cytochrome P450 systems. Furnes, B., Schlenk, D. Drug Metab. Dispos. (2005) [Pubmed]
  25. In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole. Emoto, C., Murase, S., Sawada, Y., Jones, B.C., Iwasaki, K. Drug Metab. Pharmacokinet. (2003) [Pubmed]
  26. CYP4A metabolites of arachidonic acid and VEGF are mediators of skeletal muscle angiogenesis. Amaral, S.L., Maier, K.G., Schippers, D.N., Roman, R.J., Greene, A.S. Am. J. Physiol. Heart Circ. Physiol. (2003) [Pubmed]
  27. Role of 20-hydroxyeicosatetraenoic acid in the renal and vasoconstrictor actions of angiotensin II. Alonso-Galicia, M., Maier, K.G., Greene, A.S., Cowley, A.W., Roman, R.J. Am. J. Physiol. Regul. Integr. Comp. Physiol. (2002) [Pubmed]
  28. Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in guinea pigs and mice using serial sampling. Balani, S.K., Li, P., Nguyen, J., Cardoza, K., Zeng, H., Mu, D.X., Wu, J.T., Gan, L.S., Lee, F.W. Drug Metab. Dispos. (2004) [Pubmed]
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