Reaction: (1) albendazole + [reduced NADPH—hemoprotein reductase] + O2 = albendazole S-oxide + [oxidized NADPH—hemoprotein reductase] + H2O
(2) fenbendazole + [reduced NADPH—hemoprotein reductase] + O2 = fenbendazole S-oxide + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of reaction click here.
Glossary: albendazole = methyl [5-(propylsulfanyl)-1H-benzimidazol-2-yl]carbamate
fenbendazole = methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate
Other name(s): albendazole sulfoxidase (ambiguous); albendazole hydroxylase (ambiguous); CYP3A4 (gene name); CYP2J2 (gene name); CYP1A2 (gene name)
Systematic name: albendazole,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (sulfoxide-forming)
Comments: This is one of the activities carried out by some microsomal cytochrome P-450 monooxygenases. A similar conversion is also carried out by a different microsomal enzyme (EC 1.14.13.32, albendazole monooxygenase (flavin-containing)), but it is estimated that cytochrome P-450s are responsible for 70% of the activity.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
References:
1. Moroni, P., Buronfosse, T., Longin-Sauvageon, C., Delatour, P. and Benoit, E. Chiral sulfoxidation of albendazole by the flavin adenine dinucleotide-containing and cytochrome P450-dependent monooxygenases from rat liver microsomes. Drug Metab. Dispos. 23 (1995) 160-165. [PMID: 7736906]
2. Rawden, H.C., Kokwaro, G.O., Ward, S.A. and Edwards, G. Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes. Br. J. Clin. Pharmacol. 49 (2000) 313-322. [PMID: 10759686]
3. Asteinza, J., Camacho-Carranza, R., Reyes-Reyes, R.E., Dorado-Gonzalez, V., V. and Espinosa-Aguirre, J.J. Induction of cytochrome P450 enzymes by albendazole treatment in the rat. Environ Toxicol Pharmacol 9 (2000) 31-37. [PMID: 11137466]
4. Lee, C.A., Neul, D., Clouser-Roche, A., Dalvie, D., Wester, M.R., Jiang, Y., Jones, J.P., 3rd, Freiwald, S., Zientek, M. and Totah, R.A. Identification of novel substrates for human cytochrome P450 2J2. Drug Metab. Dispos. 38 (2010) 347-356. [PMID: 19923256]
5. Wu, Z., Lee, D., Joo, J., Shin, J.H., Kang, W., Oh, S., Lee, D.Y., Lee, S.J., Yea, S.S., Lee, H.S., Lee, T. and Liu, K.H. CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob. Agents Chemother. 57 (2013) 5448-5456. [PMID: 23959307]