Minireview biotransformation of drugs in human skin

Drug Metabolism and Disposition

Volumn 37, Issue 2, 2009, Pages 247-253

  Svensson, Craig K ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLTRANSFERASE; CYTOCHROME P450; SULFOTRANSFERASE; UNSPECIFIC MONOOXYGENASE; DRUG; GLUTATHIONE TRANSFERASE; MIXED FUNCTION OXIDASE;

BIOTRANSFORMATION; DRUG METABOLISM; HUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN LOCALIZATION; SHORT SURVEY; SKIN; SKIN CELL; ARTICLE; CYTOLOGY; ENZYMOLOGY; METABOLISM; PHARMACOKINETICS; PHYSIOLOGY; SKIN ABSORPTION;

ACETYLTRANSFERASES; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; GLUTATHIONE TRANSFERASE; HUMANS; MIXED FUNCTION OXYGENASES; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; SKIN; SKIN ABSORPTION; SULFOTRANSFERASES;

EID: 59649086270     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.024794     Document Type: Short Survey

References (36)

1. Ademola JI and Maibach HI (1995) Cutaneous metabolism and penetration of methoxypsoralen, betamethasone 17-valerate, retinoic acid, nitroglycerin, and theophylline. Curr Probl Dermatol 22:201-213.
2. Anderson RJ, Kudlacek PE, and Clemens DL (1998) Sulfation of minoxidil by multiple human cytosolic sulfotransferases. Chem Biol Interact 109:53-67.
3. Baron JM, Höller D, Schiffer R, Frankenberg S, Neis M, Merk HF, and Jugert FK (2001) Expression of multiple cytochrome P450 enzymes and multidrug resistance-associated transport proteins in human skin keratinocytes. J Invest Dermatol 116:541-548.
4. Bhaiya P, Roychowdhury S, Vyas PM, Doll MA, Hein DW, and Svensson CK (2006) Bioactivation, protein haptenation and toxicity of sulfamethoxazole and dapsone in normal human dermal fibroblasts. Toxicol Appl Pharmacol 215:158-167.
5. Buhl AE, Waldon DJ, Baker CA, and Johnson GA (1990) Minoxidil sulfate is the active metabolite that stimulates hair follicles. J Invest Dermatol 95:553-557.
6. Chanda S, Bashir M, Babbar S, Koganti A, and Bley K (2008) In vitro hepatic and skin metabolism of capsaicin. Drug Metab Dispos 36:670-675.
7. Cribb AE, Lee BL, Trepanier LA, and Spielberg SP (1996) Adverse reactions to sulphonamide and sulphonamide-trimethoprim antimicrobials: clinical syndromes and pathogenesis. Adverse Drug React Toxicol Rev 15:9-50.
8. Cross SE, Anderson CC, and Roberts MS (1998) Topical penetration of commercial salicylate esters and salts using human isolated skin and clinical microdialysis studies. Br J Clin Pharmacol 46:29-35.
9. Dooley TP, Haldeman-Cahill R, Joiner J, and Wilborn TW (2000) Expression profiling of human sulfotransferase and sulfatase gene superfamilies in epithelial tissues and cultured cells. Biochem Biophys Res Commun 277:236 -245.
10. Falany CN, He D, Dumas N, Frost AR, and Falany JL (2006) Human cytosolic sulfotransferase 2B1: isoform expression, tissue specificity and subcellular localization. JSteroid Biochem Mol Biol 102:214-221.
11. Gorlewska-Roberts KM, Teitel CH, Lay JJ, Roberts DW, and Kadlubar FF (2004) Lactoperoxidase-catalyzed activation of carcinogenic aromatic and heterocyclic amines. Chem Res Toxicol 17:1659-1666.
12. Gupta A, Eggo MC, Uetrecht JP, Cribb AE, Daneman D, Rieder MJ, Shear NH, Cannon M, and Spielberg SP (1992) Drug-induced hypothyroidism: the thyroid as a target organ in hypersensitivity reactions to anticonvulsants and sulfonamides. Clin Pharmacol Ther 51:56-67.
13. Haake A, Scott GA, and Holbrook KA (2000) Structure and function of the skin: overview of the epidermis and dermis, in The Biology of the Skin (Freinkel RK and Woodley DT eds), pp 19-45, The Parthenon Publishing Group, New York.
14. Hamamoto T and Mori Y (1989) Sulfation of minoxidil in keratinocytes and hair follicles. Res Commun Chem Pathol Pharmacol 66:33-44.
15. Janmohamed A, Dolphin C, Phillips I, and Shephard E (2001) Quantification and cellular localization of expression in human skin of genes encoding flavin-containing monooxygenases and cytochromes P450. Biochem Pharmacol 62:777-786.
16. Khan FD, Roychowdhury S, Gaspari AA, and Svensson CK (2006) Immune response to xenobiotics in the skin: from contact sensitivity to drug allergy. Expert Opin Drug Metab Toxicol 2:261-272.
17. Khan FD, Vyas PM, Gaspari AA, and Svensson CK (2007) Effect of arylhydroxylamine metabolites of sulfamethoxazole and dapsone on stress signal expression in human keratino- cytes. J Pharmacol Exp Ther 323:771-777.
18. Kudlacek PE, Anderson RJ, Liebentritt DK, Johnson GA, and Huerter CJ (1995) Human skin and platelet minoxidil sulfotransferase activities: biochemical properties, correlations and contribution of thermolabile phenol sulfotransferase. J Pharmacol Exp Ther 273:582-590.
19. Nordlund JJ and Boissy RE (2000) The biology of melanocytes, in The Biology of the Skin (Freinkel RK and Woodley DT eds), pp 113-132, The Parthenon Publishing Group, New York.
20. Oesch F, Fabian E, Oesch-Bartlomowicz B, Werner C, and Landsiedel R (2007) Drug-metabolizng enzymes in the skin of man, rat, and pig. Drug Metab Rev 39:659-698.
21. Reilly TP, Lash LH, Doll MA, Hein DW, Woster PM, and Svensson CK (2000) A role for bioactivation and covalent binding within epidermal keratinocytes in sulfonamide-induced cutaneous drug reactions. J Invest Dermatol 114:1164-1173.
22. Romani N, Holzmann S, Tripp CH, Koch F, and Stoitzner P (2003) Langerhans cells - dendritic cells of the epidermis. APMIS 111:725-740.
23. Roychowdhury S, Cram AE, Aly A, and Svensson CK (2007a) Detection of haptenated proteins in organotypic human skin explant cultures exposed to dapsone. Drug Metab Dispos 35:1463-1465.
24. Roychowdhury S and Svensson CK (2005) Mechanisms of drug-induced delayed-type hyper-sensitivity reactions in the skin. AAPS J 7:E834-E846.
25. Roychowdhury S, Vyas PM, Reilly TP, Gaspari AA, and Svensson CK (2005) Characterization of the formation and localization of sulfamethoxazole-and dapsone-associated drug-protein adducts in human epidermal keratinocytes. J Pharmacol Exp Ther 314:43-52.
26. Roychowdhury S, Vyas PM, and Svensson CK (2007b) Formation and uptake of arylhydroxy-lamine-haptenated proteins in human dendritic cells. Drug Metab Dispos 35:676 -681.
27. Saeki M, Saito Y, Nagano M, Teshima R, Ozawa S, and Sawada J-I (2002) mRNA expression of multiple cytochrome P450 isozymes in four types of cultured skin cells. Int Arch Allergy Immunol 127:333-336.
28. Sanderson JP, Naisbitt DJ, Farrell J, Ashby CA, Tucker MJ, Rieder MJ, Pirmohamed M, Clarke SE, and Park BK (2007) Sulfamethoxazole and its metabolite nitroso sulfamethoxazole stimulate dendritic cell costimulatory signaling. J Immunol 178:5533-5542.
29. Smith G, Dawe RS, Clark C, Evans AT, Comrie MM, Wolf CR, Ferguson J, and Ibbotson SH (2003) Quantitative real-time reverse transcriptase-polymerase chain reaction analysis of drug metabolizing and cytoprotective genes in psoriasis and regulation by ultraviolet radiation. J Invest Dermatol 121:390-398.
30. Stinchcomb AL, Swaan PW, Ekabo O, Harris KK, Browe J, Hammell DC, Cooperman TA, and Pearsall M (2002) Straight-chain naltrexone ester prodrugs: diffusion and concurrent esterase biotransformation in human skin. J Pharm Sci 91:2571-2578.
31. Uetrecht JP, Shear NH, and Zahid N (1993) N-chlorination of sulfamethoxazole and dapsone by the myeloperoxidase system. Drug Metab Dispos 21:830-834.
32. Vyas PM, Roychowdhury S, Khan FD, Prisinzano TE, Lamba J, Schuetz EG, Blaisdell J, Goldstein JA, Munson KL, Hines RN, et al. (2006a) Enzyme-mediated protein haptenation of dapsone and sulfamethoxazole in human keratinocytes: I. Expression and role of cytochromes P450. J Pharmacol Exp Ther 319:488-496.
33. Vyas PM, Roychowdhury S, Koukouritaki SB, Hines RN, Krueger SK, Williams DE, Nauseef WM, and Svensson CK (2006b) Enzyme-mediated protein haptenation of dapsone and sulfamethoxazole in human keratinocytes: II. Expression and role of flavin-containing mono-oxygenases and peroxidases. J Pharmacol Exp Ther 319:497-505.
34. Vyas PM, Roychowdhury S, Woster PM, and Svensson CK (2005) Reactive oxygen species generation and its role in the differential cytotoxicity of the arylhydroxylamine metabolites of sulfamethoxazole and dapsone in normal human epidermal keratinocytes. Biochem Pharmacol 70:275-286.
35. Yengi LG, Xiang Q, Pan J, Scatina J, Kao J, Ball SE, Fruncillo R, Ferron G, and Roland Wolf C (2003) Quantitation of cytochrome P450 mRNA levels in human skin. Anal Biochem 316:103-110.
36. Zhu QC, Hu JH, Liu JY, Lu SW, Liu YX, and Wang J (2007) Stereoselective characteristics and mechanisms of epidermal carboxylesterase metabolism observed in HaCaT keratinocytes. Biol Pharm Bull 30:532-536.