Stereoselective metabolism of propranolol glucuronidation by human UDP-glucuronosyltransferases 2B7 and 1A9

Chirality

Volumn 22, Issue 4, 2010, Pages 456-461

  Yu, Lushan ^a   Qian, Minrong ^a   Liu, Yao ^a   Yao, Tongwei ^a   Zeng, Su ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Glucuronidation; Glucuronosyltransferase; Propranolol; Racemate; Stereoselective

Indexed keywords

GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; PROPRANOLOL;

ARTICLE; CHIRALITY; DRUG GLUCURONIDATION; ENANTIOMER; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SUBSTRATE COMPLEX; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY;

ANIMALS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUORESCENT DYES; GLUCURONOSYLTRANSFERASE; HUMANS; KINETICS; LIVER; PROPRANOLOL; RATS; RECOMBINANT PROTEINS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 77950385419     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20765     Document Type: Article

References (15)

1. Yan XF, Zhou Q, Yao TW, Zeng S, Yao HP, Yu YN. Stereoselective determination of propranolol enantiomer in transgenic cell lines expressing human cytochrome P450. Zhejiang Da Xue Xue Bao Yi Xue Ban 2003;32:116-120.
2. Silber B, Holford NH, Riegelman S. Stereoselective disposition and glucuronidation of propranolol in humans. J Pharm Sci 1982;71:699-704.
3. Yu LS, Luan LJ, Shao Q, Zeng S. Direct determination of S(-)- and R(+)-propranolol glucuronide in rat hepatic microsomes by RP-HPLC. Biomed Chromatogr 2004;18:833-837.
4. Coffman BL, King CD, Rios GR, Tephly TR. The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268). Drug Metab Dispos 1998;26:73-77.
5. Li X, Yu YN, Zhu GJ, Qian YL. Cloning of UGT1A9 cDNA from liver tissues and its expression in CHL cells. World J Gastroenterol 2001;7:841-845.
6. Hanioka N, Hayashi K, Shimizudani T, Nagaoka K, Koeda A, Naito S, Narimatsu S. Stereoselective glucuronidation of propranolol in human and cynomolgus monkey liver microsomes: role of human hepatic UDP- glucuronosyltransferase isoforms, UGT1A9, UGT2B4 and UGT2B7. Pharmacology 2008;82:293-303.
7. Sten T, Qvisen S, Uutela P, Luukkanen L, Kostiainen R, Finel M. Prominent but reverse stereoselectivity in propranolol glucuronidation by human UDP-glucuronosyltransferases 1A9 and 1A10. Drug Metab Dispos 2006;34:1488-1494.
8. Qian M, Chen S, Li X, Zeng S. Cloning and expression of human UDP-glucuronosyltransferase 1A4 in Bac-to-Bac system. Biochem Biophys Res Commun 2004;319:386-392.
9. Yu LS, Lu SJ, Lin YJ, Zeng S. Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases. Biochem Pharmacol 2007;73:842-851.
10. Houston JB, Kenworthy KE. In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 2000;28:246-254.
11. Tougou K, Gotou H, Ohno Y, Nakamura A. Stereoselective glucuronidation and hydroxylation of etodolac by UGT1A9 and CYP2C9 in man. Xenobiotica 2004;34:449-461.
12. Sakaguchi K, Green M, Stock N, Reger TS, Zunic J, King C. Glucuronidation of carboxylic acid containing compounds by UDP-glucuronosyltransferase isoforms. Arch Biochem Biophys 2004;424:219-225.
13. Jin C, Miners JO, Lillywhite KJ, Mackenzie PI. Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferaseglucuronidating carboxylic acid-containing drugs. J Pharmacol Exp Ther 1993;264:475-479.
14. Luan LJ, Shao Q, Ma JY, Zeng S. Stereoselective urinary excretion of S(-)- and R(+)-propranolol glucuronide following oral administration of RS-propranolol in Chinese Han subjects. World J Gastroenterol 2005;11:1822-1824.
15. Luan LJ, Shao Q, Zeng S. Stereoselectivity and interaction between the glucuronidation of S-(-)- and R-(+)-propranolol in rat hepatic microsomes pretreated with different inducers. Pharmazie 2005;60:221-224.