Nevirapine bioactivation and covalent binding in the skin

Chemical Research in Toxicology

Volumn 26, Issue 3, 2013, Pages 410-421

  Sharma, Amy M ^a   Klarskov, Klaus ^b   Uetrecht, Jack ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

12 HYDROXYNEVIRAPINE SULFATE; ADENOSINE 3' PHOSPHATE 5' PHOSPHOSULFATE; DRUG METABOLITE; GLUTATHIONE; NEVIRAPINE; SULFOTRANSFERASE; UNCLASSIFIED DRUG;

ADULT; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CELL FRACTIONATION; CELL PROLIFERATION; CELL SEPARATION; CONTROLLED STUDY; COVALENT BOND; CYTOLYSIS; DERMIS; DRUG BINDING SITE; DRUG ERUPTION; DRUG HYDROXYLATION; DRUG OXIDATION; DRUG SOLUBILITY; DRUG SULFATION; ENZYME ACTIVITY; EPIDERMIS; FEMALE; HISTOPATHOLOGY; HUMAN; HUMAN CELL; HUMAN TISSUE; IMMUNOBLOTTING; IMMUNOLOGICAL TOLERANCE; MALE; MOUSE; NONHUMAN; RAT; SULFATION; TISSUE HOMOGENATE; TREATMENT DURATION;

ANIMALS; EXANTHEMA; FEMALE; HIV INFECTIONS; HUMANS; LIVER; MICE; MICE, INBRED BALB C; MICE, INBRED C57BL; NADP; NEVIRAPINE; PHOSPHOADENOSINE PHOSPHOSULFATE; PROTEIN BINDING; PROTEINS; RATS; REVERSE TRANSCRIPTASE INHIBITORS; SKIN;

EID: 84875135492     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx3004938     Document Type: Article

References (16)

1. Shenton, J. M., Teranishi, M., Abu-Asab, M. S., Yager, J. A., and Uetrecht, J. P. (2003) Characterization of a potential animal model of an idiosyncratic drug reaction: nevirapine-induced skin rash in the rat Chem. Res. Toxicol. 16, 1078-1089
2. Pollard, R. B., Robinson, P., and Dransfield, K. (1998) Safety profile of nevirapine, a nonnucleoside reverse transcriptase inhibitor for the treatment of human immunodeficiency virus infection Clin. Ther. 20, 1071-1092
3. Bersoff-Matcha, S. J., Miller, W. C., Aberg, J. A., van der Horst, C., Hamrick, H. J., Powderly, W. G., and Mundy, L. M. (2001) Sex differences in nevirapine rash Clin. Infect. Dis. 32, 124-129
4. Chen, X., Tharmanathan, T., Mannargudi, B., Gou, H., and Uetrecht, J. P. (2009) A study of the specificity of lymphocytes in nevirapine-induced skin rash J. Pharmacol. Exp. Ther. 331, 836-841
5. Keane, N., (2007) Proceedings of the 4th International AIDS Society Conference on HIV Pathogenesis, Treatment and Prevention, Sydney, Australia.
6. Chen, J., Mannargudi, B. M., Xu, L., and Uetrecht, J. (2008) Demonstration of the metabolic pathway responsible for nevirapine-induced skin rash Chem. Res. Toxicol. 21, 1862-1870
7. Banoglu, E. and Duffel, M. W. (1997) Studies on the interactions of chiral secondary alcohols with rat hydroxysteroid sulfotransferase STa Drug Metab. Dispos. 25, 1304-1310
8. Oesch, F., Fabian, E., Oesch-Bartlomowicz, B., Werner, C., and Landsiedel, R. (2007) Drug-metabolizing enzymes in the skin of man, rat, and pig Drug Metab. Rev. 39, 659-698
9. Sharma, A. M., Li, Y., Novalen, M., Hayes, M. A., and Uetrecht, J. (2012) Bioactivation of Nevirapine to a Reactive Quinone Methide: Implications for Liver Injury Chem. Res. Toxicol. 25, 1708-1719
10. Lichti, U., Anders, J., and Yuspa, S. H. (2008) Isolation and short-term culture of primary keratinocytes, hair follicle populations and dermal cells from newborn mice and keratinocytes from adult mice for in vitro analysis and for grafting to immunodeficient mice Nat. Protocols 3, 799-810
11. Chauret, N., Gauthier, A., and Nicoll-Griffith, D. A. (1998) Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes Drug Metab. Dispos. 26, 1-4
12. Uetrecht, J. (2007) Idiosyncratic drug reactions: past, present, and future Chem. Res. Toxicol. 21, 84-92
13. Merk, H. F. (2009) Drug skin metabolites and allergic drug reactions Curr. Opin. Allergy Clin. Immunol. 9, 311-315
14. Gutowska-Owsiak, D. and Ogg, G. S. (2012) The Epidermis as an adjuvant J. Invest. Dermatol. 132, 940-948
15. Havlir, D., Cheeseman, S. H., Mclaughlin, M., Murphy, R., Erice, A., Spector, S. A., Greenough, T. C., Sullivan, J. L., Hall, D., Myers, M., Lamson, M., and Richman, D. D. (1995) High-dose nevirapine: safety, pharmacokinetics, and antiviral effect in patients with human immunodeficiency virus infection J. Infect. Dis. 171, 537-545
16. Pichler, W. J. (2003) Drug-induced autoimmunity Curr. Opin. Allergy Clin. Immunol. 3, 249-253