Human arylacetamide deacetylase is responsible for deacetylation of rifamycins: Rifampicin, rifabutin, and rifapentine

Biochemical Pharmacology

Volumn 82, Issue 11, 2011, Pages 1747-1756

  Nakajima, Akinori ^a   Fukami, Tatsuki ^a   Kobayashi, Yuki ^a   Watanabe, Akinobu ^a   Nakajima, Miki ^a   Yokoi, Tsuyoshi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Arylacetamide deacetylase; Cytotoxicity; Gene induction; Rifamycins

Indexed keywords

ACYLTRANSFERASE; ARYLACETAMIDE DEACETYLASE; CARBOXYLESTERASE; CYTOCHROME P450 3A4; RIFABUTIN; RIFAMPICIN; RIFAPENTINE; UNCLASSIFIED DRUG;

ADENOVIRUS; ARTICLE; CONTROLLED STUDY; DEACETYLATION; DRUG CYTOTOXICITY; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVITY; HUMAN; HUMAN CELL; HYDROLYSIS; LIVER CELL; PLASMID; PRIORITY JOURNAL;

ACETYLATION; ANTITUBERCULAR AGENTS; CARBOXYLIC ESTER HYDROLASES; CELL SURVIVAL; CYTOCHROME P-450 CYP3A; CYTOTOXINS; ENZYME INDUCTION; HEK293 CELLS; HEP G2 CELLS; HUMANS; KINETICS; MICROSOMES, LIVER; PROMOTER REGIONS, GENETIC; RECOMBINANT PROTEINS; RIFABUTIN; RIFAMPIN;

EID: 80255130599     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.08.003     Document Type: Article

References (37)

1. Yamaoka T. Rifampicin use in MRSA infections in developing countries. Reply to the letter to the editor by D.S. Neogi. J Infect Chemother 2009;15:205.
2. S. Fresz Chemical and biological properties of rifampicin Antibiot Chemother 16 1970 316 351
3. W.J. Burman, K. Gallicano, and C. Peloquin Comparative pharmacokinetics and pharmacodynamics of the rifamycin antibacterials Clin Pharmacokinet 40 2001 327 341 (Pubitemid 32565595)
4. C.A. Jamis-Dow, A.G. Katki, J.M. Collins, and R.W. Klecker Rifampin and rifabutin and their metabolism by human liver esterases Xenobiotica 27 1997 1015 1024 (Pubitemid 27450594)
5. T.K. Chang Activation of pregnane X receptor (PXR) and constitutive androstane receptor (CAR) by herbal medicines AAPS J 11 2009 590 601
6. J.D. Lazar, and K.D. Wilner Drug interactions with fluconazole Rev Infect Dis 12 1990 S327 S333
7. W.W. Yew, and C.C. Leung Antituberculosis drugs and hepatotoxicity Respirology 11 2006 699 707 (Pubitemid 44581433)
8. G.R. Sarma, C. Immanuel, S. Kailasam, A.S. Narayana, and P. Venkatesan Rifampin-induced release of hydrazine from isoniazid. A possible cause of hepatitis during treatment of tuberculosis with regimens containing isoniazid and rifampin Am Rev Respir Dis 133 1986 1072 1075 (Pubitemid 16090015)
9. E. Iatsimirskaia, S. Tulebaev, E. Storozhuk, I. Utkin, D. Smith, and N. Gerber Metabolism of rifabutin in human enterocyte and liver microsomes: kinetic parameters, identification of enzyme systems, and drug interactions with macrolides and antifungal agents Clin Pharmacol Ther 61 1997 554 562 (Pubitemid 27261759)
10. M.K. Ross, and J.A. Crow Human carboxylesterases and their role in xenobiotic and endobiotic metabolism J Biochem Mol Toxicol 21 2007 187 196 (Pubitemid 350194379)
11. M.R. Probst, P. Jeno, and U.A. Meyer Purification and characterization of a human liver arylacetamide deacetylase Biochem Biophys Res Commun 177 1991 453 459
12. M.R. Probst, M. Beer, D. Beer, P. Jeno, U.A. Meyer, and R. Gasser Human liver arylacetamide deacetylase. Molecular cloning of a novel esterase involved in the metabolic activation of arylamine carcinogens with high sequence similarity to hormone-sensitive lipase J Biol Chem 269 1994 21650 21656
13. R. Tiwari, R. Köffel, and R. Schneiter An acetylation/deacetylation cycle controls the export of sterols and steroids from S. cerevisiae EMBO J 26 2007 5109 5119 (Pubitemid 350261287)
14. A. Watanabe, T. Fukami, M. Nakajima, M. Takamiya, Y. Aoki, and T. Yokoi Human arylacetamide deacetylase is a principal enzyme in flutamide hydrolysis Drug Metab Dispos 37 2009 1513 1520
15. A. Watanabe, T. Fukami, S. Takahashi, Y. Kobayashi, N. Nakagawa, and M. Nakajima Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen Drug Metab Dispos 38 2010 1532 1537
16. T. Fukami, S. Takahashi, N. Nakagawa, T. Maruichi, M. Nakajima, and T. Yokoi In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human carboxylesterase activities Drug Metab Dispos 38 2010 2173 2178
17. E. Heymann, and K. Krisch Phospholic acid-bis-(p-nitro-phenylester), a new inhibitor of microsomal carboxylesterases Hoppe Seylers Z Physiol Chem 348 1967 609 619
18. S. Yamaori, N. Fujiyama, M. Kushihara, T. Funahashi, T. Kimura, and I. Yamamoto Involvement of human blood arylesterases and liver microsomal carboxylesterases in nafamostat hydrolysis Drug Metab Pharmacokinet 21 2006 147 155
19. K. Iwatsubo Studies on the classification of the enzymes hydrolysing ester-form drugs in liver microsomes Jpn J Pharmacol 15 1965 244 265
20. E. Heilbronn Action of fluoride on cholinesterase. I. On the mechanism of inhibition Acta Chem Scand 19 1965 1333 1346
21. G. Johnson, and S.W. Moore Cholinesterase-like catalytic antibodies: reaction with substrates and inhibitors Mol Immunol 37 2000 707 719 (Pubitemid 32244119)
22. P.B. Costello, and F.A. Green Identification and partial purification of the major aspirin hydrolyzing enzyme in human blood Arthritis Rheum 26 1983 541 547 (Pubitemid 13120245)
23. H. Hosomi, S. Akai, K. Minami, Y. Yoshikawa, T. Fukami, and M. Nakajima An in vitro drug-induced hepatotoxicity screening system using CYP3A4-expressing and γ-glutamylcysteine synthetase knockdown cells Toxicol In Vitro 24 2010 1032 1038
24. T. Takada, M. Ogino, M. Miyata, M. Shimada, K. Nagata, and Y. Yamazoe Differences in transactivation between rat CYP3A1 and human CYP3A4 genes by human pregnane X receptor Drug Metab Pharmacokinet 19 2004 103 113
25. Y. Tsuchiya, M. Nakajima, S. Kyo, T. Kanaya, M. Inoue, and T. Yokoi Human CYP1B1 is regulated by estradiol via estrogen receptor Cancer Res 64 2004 3119 3125 (Pubitemid 38581412)
26. G. Xu, W. Zhang, M.K. Ma, and H.L. McLeod Human carboxylesterase 2 is commonly expressed in tumor tissue and is correlated with activation of irinotecan Clin Cancer Res 8 2002 2605 2611 (Pubitemid 34856347)
27. T. Tabata, M. Katoh, S. Tokudome, M. Hosakawa, K. Chiba, and M. Nakajima Bioactivation of capecitabine in human liver: involvement of the cytosolic enzyme on 5′-deoxy-5-fluorocytidine formation Drug Metab Dispos 32 2004 762 767 (Pubitemid 38821879)
28. J.G. Bourne, H.O.J. Collier, and G.F. Somers Succinylcholine (succinoylcholine), muscle-relaxant of short action Lancet 1 1952 1225 1229
29. C.L. Morton, R.M. Wadkins, M.K. Dnaks, and P.M. Potter The anticancer prodrug CPT-11 is a potent inhibitor of acetylcholinesterase but is rapidly catalyzed to SN-38 by butyrylcholinesterase Cancer Res 59 1999 1458 1463 (Pubitemid 29160111)
30. D.I. Draganov, P.L. Stetson, C.E. Watson, S.S. Billecke, and B.N. La Du Rabbit serum paraoxonase 3 (PON3) is a high density lipoprotein-associated lactonase and protects low density lipoprotein against oxidation J Biol Chem 275 2000 33435 33442
31. S.L. Primo-Parmo, R.C. Sorenson, J. Teiber, and B.N. La Du The human serum paraoxonase/arylesterase gene (PON1) is one member of a multigene family Genomics 33 1996 498 507 (Pubitemid 26159866)
32. E.G. Erdos, C.R. Debay, and M.P. Westerman Arylesterases in blood: effect of calcium and inhibitors Biochem Pharmacol 5 1960 173 186
33. T. Hioki, T. Fukami, M. Nakajima, and T. Yokoi Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis Drug Metab Dispos 39 2011 1345 1352
34. S. Kenwright, and A.J. Levi Sites of competition in the selective hepatic uptake of rifamycin-SV, flavaspidic acid, bilirubin, and bromsulphthalein Gut 15 1974 220 226
35. P.J. Scheuer, J.A. Summerfield, S. Lal, and S. Sherlock Rifampicin hepatitis. A clinical and histological study Lancet 16 1974 421 425
36. T. Jaakkola, J.T. Backman, M. Neuvonen, J. Laitila, and P.J. Neuvonen Effect of rifampicin on the pharmacokinetics of pioglitazone Br J Clin Pharmacol 61 2006 70 78 (Pubitemid 43381239)
37. Y. Adachi, T. Nanno, M. Yamashita, S. Ueshima, and T. Yamamoto Induction of rat liver bilirubin-conjugating enzymes and glutathione S-transferase by rifampicin Gastroenterol Jpn 20 1985 104 110 (Pubitemid 15059858)