Activation of the antiviral prodrug oseltamivir is impaired by two newly identified carboxylesterase 1 variants

Drug Metabolism and Disposition

Volumn 37, Issue 2, 2009, Pages 264-267

  Zhu, Hao Jie ^a   Markowitz, John S ^a  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETAMIDO 5 AMINO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLIC ACID; CARBOXYLESTERASE; DRUG METABOLITE; ENZYME VARIANT; HYDROLASE; METHYLPHENIDATE; OSELTAMIVIR; PRODRUG;

ARTICLE; CELL LINE; CONTROLLED STUDY; DRUG ACTIVATION; DRUG HYDROLYSIS; DRUG METABOLISM; ENZYME ACTIVITY; HUMAN; HUMAN CELL; INFLUENZA; INFLUENZA VIRUS A; INFLUENZA VIRUS B; LIVER; METABOLITE; MUTATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; TOXICITY;

ALLELES; AMINO ACID SUBSTITUTION; ANTIVIRAL AGENTS; CARBOXYLIC ESTER HYDROLASES; CELL LINE; HUMANS; HYDROLYSIS; MUTATION; ORTHOMYXOVIRIDAE; OSELTAMIVIR; PLATELET AGGREGATION INHIBITORS; PRODRUGS;

INFLUENZAVIRUS A;

EID: 59649111001     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.024943     Document Type: Article

References (19)

1. Anand SS, Kim KB, Padilla S, Muralidhara S, Kim HJ, Fisher JW, and Bruckner JV (2006) Ontogeny of hepatic and plasma metabolism of deltamethrin in vitro: role in age-dependent acute neurotoxicity. Drug Metab Dispos 34:389-397.
2. Geshi E, Kimura T, Yoshimura M, Suzuki H, Koba S, Sakai T, Saito T, Koga A, Muramatsu M, and Katagiri T (2005) A single nucleotide polymorphism in the carboxylesterase gene is associated with the responsiveness to imidapril medication and the promoter activity. Hyper- tens Res 28:719-725.
3. Hosokawa M, Furihata T, Yaginuma Y, Yamamoto N, Watanabe N, Tsukada E, Ohhata Y, Kobayashi K, Satoh T, and Chiba K (2008) Structural organization and characterization of the regulatory element of the human carboxylesterase (CES1A1 and CES1A2) genes. Drug Metab Pharmacokinet 23:73-84.
4. Imai T, Imoto M, Sakamoto H, and Hashimoto M (2005) Identification of esterases expressed in Caco-2 cells and effects of their hydrolyzing activity in predicting human intestinal absorption. Drug Metab Dispos 33:1185-1190.
5. Imai T, Taketani M, Shii M, Hosokawa M, and Chiba K (2006) Substrate specificity of carboxylesterase isozymes and their contribution to hydrolase activity in human liver and small intestine. Drug Metab Dispos 34:1734-1741.
6. Kadner SS, Katz J, and Finlay TH (1992) Esterase-1: developmental expression in the mouse and distribution of related proteins in other species. Arch Biochem Biophys 296:435-441.
7. Karanth S and Pope C (2000) Carboxylesterase and A-esterase activities during maturation and aging: relationship to the toxicity of chlorpyrifos and parathion in rats. Toxicol Sci 58:282-289.
8. Morgan EW, Yan B, Greenway D, and Parkinson A (1994) Regulation of two rat liver microsomal carboxylesterase isozymes: species differences, tissue distribution, and the effects of age, sex, and xenobiotic treatment of rats. Arch Biochem Biophys 315:513-526.
9. Moser VC, Chanda SM, Mortensen SR, and Padilla S (1998) Age- and gender-related differences in sensitivity to chlorpyrifos in the rat reflect developmental profiles of esterase activities. Toxicol Sci 46:211-222.
10. Padilla S, Sung HJ, and Moser VC (2004) Further assessment of an in vitro screen that may help identify organophosphorus pesticides that are more acutely toxic to the young. J Toxicol Environ Health A 67:1477-1489.
11. Patrick KS, Straughn AB, Minhinnett RR, Yeatts SD, Herrin AE, DeVane CL, Malcolm R, Janis GC, and Markowitz JS (2007) Influence of ethanol and gender on methylphenidate pharma- cokinetics and pharmacodynamics. Clin Pharmacol Ther 81:346-353.
12. Ross MK and Crow JA (2007) Human carboxylesterases and their role in xenobiotic and endobiotic metabolism. J Biochem Mol Toxicol 21:187-196.
13. Satoh T and Hosokawa M (2006) Structure, function and regulation of carboxylesterases. Chem Biol Interact 162:195-211.
14. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, and Yan B (2006) Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 319:1477-1484.
15. Sun Z, Murry DJ, Sanghani SP, Davis WI, Kedishvili NY, Zou Q, Hurley TD, and Bosron WF (2004) Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther 310:469-476.
16. Tang M, Mukundan M, Yang J, Charpentier N, LeCluyse EL, Black C, Yang D, Shi D, and Yan B (2006) Antiplatelet agents aspirin and clopidogrel are hydrolyzed by distinct carboxyles- terases, and clopidogrel is transesterificated in the presence of ethyl alcohol. J Pharmacol Exp Ther 319:1467-1476.
17. Williams ET, Ehsani ME, Wang X, Wang H, Qian YW, Wrighton SA, and Perkins EJ (2008) Effect of buffer components and carrier solvents on in vitro activity of recombinant human carboxylesterases. J Pharmacol Toxicol Methods 57:138-144.
18. Yoshimura M, Kimura T, Ishii M, Ishii K, Matsuura T, Geshi E, Hosokawa M, and Muramatsu M (2008) Functional polymorphisms in carboxylesterase1A2 (CES1A2) gene involves specific protein 1 (Sp1) binding sites. Biochem Biophys Res Commun 369:939-942.
19. Zhu HJ, Patrick KS, Yuan HJ, Wang JS, Donovan JL, DeVane CL, Malcolm R, Johnson JA, Youngblood GL, Sweet DH, et al. (2008) Two CES1 gene mutations lead to dysfunctional carboxylesterase 1 activity in man: clinical significance and molecular basis. Am J Hum Genet 82:1241-1248.