Chiral Inhibition of Rivaroxaban Derivatives Towards UDP-Glucuronosyltransferase (UGT) Isoforms

Chirality

Volumn 27, Issue 12, 2015, Pages 936-943

  Yao, Zhuhua ^a   Liu, Yong Zhe ^c   Ma, Ai Lun ^b   Wang, Shu Fen ^c   Lu, Dan ^c   Hu, Cui Min ^c   Zhang, Yan Yan ^d   Wang, Haina ^e   Hu, Lingyun ^f   Deng, Jun ^b   Yang, Kun ^c   Fang, Zhong Ze ^c  

^a Tianjin Union Medicine Centre   (China)

^b TIANJIN UNIVERSITY   (China)

^c TIANJIN MEDICAL UNIVERSITY   (China)

^d DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^e SHANDONG UNIVERSITY   (China)

^f SHANDONG CANCER HOSPITAL AND INSTITUTE   (China)

Author keywords

chirality; drug drug interaction; rivaroxaban; UDP glucuronosyltransferases (UGTs)

Indexed keywords

5 BROMO N [[ 2 OXO 3 [4 (3 OXOMORPHOLIN 4 YL) PHENYL]-1,3 OXAZOLIDIN 5 YL]METHYL] THIOPENE 2 CARBOXAMIDE; 5 CHLORO N [[ 2 OXO 3 [4 (3 OXOMORPHOLIN 4 YL) PHENYL] 1,3 OXAZOLIDIN 5 YL]METHYL] THIOPENE 2 CARBOXAMIDE; 6 CHLORO N [[ 2 OXO 3 [4 (3 OXOMORPHOLIN 4 YL) PHENYL]-1,3 OXAZOLIDIN 5 YL]METHYL] THIOPENE 2 CARBOXAMIDE; GLUCURONOSYLTRANSFERASE; N [[ 2 OXO 3 [4 (3 OXOMORPHOLIN 4 YL) PHENYL]-1,3 OXAZOLIDIN 5 YL]METHYL] THIOPENE 2 CARBOXAMIDE; RIVAROXABAN; UNCLASSIFIED DRUG; BLOOD CLOTTING FACTOR 10A INHIBITOR; ISOENZYME;

ARTICLE; CHIRALITY; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG INHIBITION; DRUG SYNTHESIS; ENZYME STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; IN VITRO STUDY; LIGAND BINDING; LIMIT OF DETECTION; MOLECULAR DOCKING; PRIORITY JOURNAL; SIGNAL NOISE RATIO; ANTAGONISTS AND INHIBITORS; CHEMISTRY; STEREOISOMERISM;

FACTOR XA INHIBITORS; GLUCURONOSYLTRANSFERASE; ISOENZYMES; RIVAROXABAN; STEREOISOMERISM;

EID: 84946230342     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22505     Document Type: Article

References (22)

1. Depasse F, Busson J, Mnich J,. Effect of BAY 59-7939-a novel, oral, direct factor Xa inhibitor-on clot-bound factor Xa activity in vitro. J Thromb Haemost 2005; 3: P1104.
2. Roehrig S, Straub A, Pohlmann J,. Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl} methyl) thiophene- 2-carboxamide (BAY 59-7939): an oral, direct factor Xa inhibitor. J Med Chem 2005; 48: 5900-5908.
3. Weinz C, Schwarz T, Kubitza D,. Metabolism and excretion of rivaroxaban, an oral, direct factor Xa inhibitor, in rats, dogs, and humans. Drug Metab Dispos 2009; 37: 1056-1064.
4. Mueck W, Kubitza D, Becka M,. Co-administration of rivaroxaban with drugs that share its elimination pathways: pharmacokinetic effects in healthy subjects. Br J Clin Pharmacol 2013; 76: 455-466.
5. Fang ZZ, Cao YF, Hu CM, Hong M, Sun XY, Ge GB, Liu Y, Zhang YY, Yang L, Sun HZ,. Structure-inhibition relationship of ginsenosides towards UDP-glucuronosyltransferases (UGTs). Toxicol Appl Pharmacol 2013; 267: 149-154.
6. Rowland A, Miners JO, Mackenzie PI,. The UDP-glucuronosyltransferases: their role in drug metabolism and detoxification. Int J Biochem Cell Biol 2013; 45: 1121-1132.
7. Chen S, Yueh MF, Bigo C, Barbier O, Wang K, Karin M, Nguyen N, Tukey RH,. Intestinal glucuronidation protects against chemotherapy-induced toxicity by irinotecan (CPT-11). Proc Natl Acad Sci U S A 2013; 110: 19143-19148.
8. Yu J, Han JC, Gao YJ,. Biotransformation of glucoaurantio-obtusin towards aurantio-obtusin increases the toxicity of irinotecan through increased inhibition towards SN-38 glucuronidation. Phytother Res 2014; 28: 1577-1580.
9. Wei J, Ye X, Liu T,. Toxicity magnification of irinotecan's toxicity by levothyroxine through inhibition of SN-38 glucuronidation. Lat Am J Pharm 2014; 33: 1385-1388.
10. Wang H, Fang ZZ, Zheng Y, Zhou K, Hu C, Krausz KW, Sun D, Idle JR, Gonzalez FJ,. Metabolic profiling of praziquantel enantiomers. Biochem Pharmacol 2014; 90: 166-178.
11. Zucker SD, Qin X, Rouster SD, Yu F, Green RM, Keshavan P, Feinberg J, Sherman KE,. Mechanism of indinavir-induced hyperbilirubinemia. Proc Natl Acad Sci U S A 2001; 98: 12671-12676.
12. Liu M, Zhang D, Yang M, Zhao T, Wang X, Zhang Y, Han J, Liu H,. Pharmacokinetics of terazosin enantiomers in healthy Chinese male subjects. Chirality 2012; 24: 1047-1050.
13. Sun SY, Wang YQ, Li LP, Wang L, Zeng S, Zhou H, Jiang HD,. Stereoselective interaction between tetrahydropalmatine enantiomers and CYP enzymes in human liver microsomes. Chirality 2013; 25: 43-47.
14. Fang ZZ, Wang H, Cao YF, Sun DX, Wang LX, Hong M, Huang T, Chen JX, Zeng J,. Enantioselective inhibition of carprofen towards UDP- glucuronosyltransferase (UGT) 2B7. Chirality 2015; 27: 189-193.
15. Fang ZZ, He RR, Cao YF, Tanaka N, Jiang C, Krausz KW, Qi Y, Dong PP, Ai CZ, Sun XY, Hong M, Ge GB, Gonzalez FJ, Ma XC, Sun HZ,. A model of in vitro UDP-glucuronosyltransferase inhibition by bile acids predicts possible metabolic disorders. J Lipid Res 2013; 54: 3334-3344.
16. Radominska-Pandya A, Bratton SM, Redinbo MR, Miley MJ,. The crystal structure of human UDP-glucuronosyltransferase 2B7 C-terminal end is the first mammalian UGT target to be revealed: the significance for human UGTs from both the 1A and 2B families. Drug Metab Rev 2010; 42: 133-144.
17. Gao X, Qu H, Ai CZ, Cao YF, Huang T, Chen JX, Zeng J, Sun XY, Hong M, Gonzalez FJ, Liu Z, Fang ZZ,. Regulation profile of phosphatidylcholines (PCs) and lysophosphatidylcholines (LPCs) components towards UDP-glucuronosyltransferases (UGTs) isoforms. Xenobiotica 2015; 45: 197-206.
18. Liu X, Huang T, Chen JX, Zeng J, Fan XR, Xu-Zhu YZW, Sun XY, Hong M, Sun HZ,. Arbidol exhibits strong inhibition towards UDP-glucuronosyltransferase (UGT) 1A9 and 2B7. Pharmazie 2013; 68: 945-950.
19. Fu JF, Ren QY, Zhang NY, Gao B, Tu YY, Fu GQ, Li DH, Zhang YS,. Inhibition potential of glimepiride (gli) towards important UDP-glucuronosyltransferase (UGT) isoforms in human liver. Pharmazie 2012; 67: 715-717.
20. Lankisch TO, Gillman TC, Erichsen TJ, Ehmer U, Kalthoff S, Freiberg N, Munzel PA, Manns MP, Strassburg CP,. Aryl hydrocarbon receptor-mediated regulation of the human estrogen and bile acid UDP-glucuronosyltransferase 1A3 gene. Arch Toxicol 2008; 82: 573-582.
21. Erichsen TJ, Aehlen A, Ehmer U, Kalthoff S, Manns MP, Strassburg CP,. Regulation of the human bile acid UDP-glucuronosyltransferase 1A3 by the farnesoid X receptor and bile acids. J Hepatol 2010; 52: 570-578.
22. Wang Z, Wong T, Hashizume T, Dickmann LZ, Scian M, Koszewski NJ, Goff JP, Horst RL, Chaudhry AS, Schuetz EG, Thummel KE,. Human UGT1A4 and UGT1A3 conjugate 25-hydroxyvitamin D3: metabolite structure, kinetics, inducibility, and interindividual variability. Endocrinology 2014; 155: 2052-2063.