In vitro metabolism of irosustat, a novel steroid sulfatase inhibitor: Interspecies comparison, metabolite identification, and metabolic enzyme identification

Drug Metabolism and Disposition

Volumn 39, Issue 7, 2011, Pages 1235-1246

  Ventura, Verònica ^a   Solà, Josep ^a   Celma, Carles ^a   Peraire, Concepción ^a   Obach, Rosendo ^a  

^a IPSEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

667 COUMARIN; COUMATE 667; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; DRUG METABOLITE; GLUCURONOSYLTRANSFERASE; IROSUSTAT; IROSUSTAT GLUCURONIDE; IROSUSTAT SULFATE; SULFOTRANSFERASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DOG; DRUG HYDROXYLATION; DRUG METABOLISM; FEMALE; HAPLORHINI; HUMAN; HYDROLYSIS; IN VITRO STUDY; LIVER CELL; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SPECIES COMPARISON; SPECIES DIFFERENCE;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOGS; ENZYME INHIBITORS; FEMALE; HUMANS; MACACA FASCICULARIS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICROSOMES, LIVER; RATS; RATS, SPRAGUE-DAWLEY; SPECIES SPECIFICITY; STERYL-SULFATASE; SULFONIC ACIDS;

CANIS FAMILIARIS; RATTUS;

EID: 79959405162     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.038315     Document Type: Article

References (22)

1. Bohnert T and Gan LS (2010) The role of drug metabolism in drug discovery, in Enzyme Inhibition in Drug Discovery and Development: The Good and the Bad (Lu C and Li AP eds) pp 91-176, John Wiley & Sons, Hoboken, NJ.
2. Foster PA (2008) Steroid metabolism in breast cancer. Minerva Endocrinol 33:27-37.
3. Foster PA, Newman SP, Chander SK, Stengel C, Jhalli R, Woo LL, Potter BV, Reed MJ, and Purohit A (2006) In vivo efficacy of STX213, a second-generation steroid sulfatase inhibitor, for hormone-dependent breast cancer therapy. Clin Cancer Res 12:5543-5549. (Pubitemid 44497272)
4. Gomez-Lechon MJ, Donato MT, Ponsoda X, Jover R, and Castell JV (1992) Experimental in vitro models to evaluate hepatotoxicity, in In Vitro Alternatives to Animal Pharmacotoxicology (Castell JV and Gomez-Lechon MJ eds) pp 92-107, Farmaindustria, Madrid.
5. Ho YT, Purohit A, Vicker N, Newman SP, Robinson JJ, Leese MP, Ganeshapillai D, Woo LW, Potter BV, and Reed MJ (2003) Inhibition of carbonic anhydrase II by steroidal and non-steroidal sulphamates. Biochem Biophys Res Commun 305:909-914. (Pubitemid 36597850)
6. Ireson CR, Chander SK, Purohit A, Parish DC, Woo LW, Potter BV, and Reed MJ (2004) Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats. Br J Cancer 91:1399-1404. (Pubitemid 39424804)
7. Ireson CR, Parish D, Purohit A, Woo LW, Potter BV, Chander SK, and Reed MJ (2003) Development of a sensitive high-performance liquid chromatography method for the detection of 667 COUMATE in vivo. J Steroid Biochem Mol Biol 84:337-342. (Pubitemid 36514848)
8. Kauffman FC, Sharp S, Allan BB, Burchell A, and Coughtrie MWH (1998)Microsomal steroid sulfatase: interactions with cytosolic steroid sulfotransferases. Chem Biol Interact 109:169-182. (Pubitemid 28161112)
9. Kawano S, Kamataki T, Yasumori T, Yamazoe Y, and Kato R (1987) Purification of human liver cytochrome P-450 catalyzing testosterone 6 β-hydroxylation. J Biochem 102:493-501.
10. Lake BG (1987) Preparations and characterization of microsomal fractions for studies on xenobiotics metabolism, in Biochemical Toxicology: A Practical Approach (Snell K and Mullock B eds) pp 183-215, IRL Press, Oxford, UK.
11. Lloyd MD, Pederick RL, Natesh R, Woo LW, Purohit A, Reed MJ, Acharya KR, and Potter BV (2005) Crystal structure of human carbonic anhydrase II at 1.95 Å resolution in complex with 667-coumate, a novel anti-cancer agent. Biochem J 385:715-720. (Pubitemid 40208831)
12. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
13. Palmieri C, Januszewski A, Stanway S, and Coombes RC (2011) Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert Rev Anticancer Ther 11:179-183.
14. 14C]coumarin by rat hepatic microsomes. Xenobiotica 21:499-514.
15. Purohit A, Woo LW, Potter BV, and Reed MJ (2000) In vivo inhibition of estrone sulfatase activity and growth of nitrosomethylurea-induced mammary tumors by 667 COUMATE. Cancer Res 60:3394-3396. (Pubitemid 30482153)
16. Reed MJ, Purohit A, Woo LW, Newman SP, and Potter BV (2005) Steroid sulfatase: molecular biology, regulation, and inhibition. Endocr Rev 26:171-202.
17. Seglen PO (1976) Preparation of isolated rat liver cells. Methods Cell Biol 13:29-83.
18. Selcer KW, Kabler H, Sarap J, Xiao Z, and Li PK (2002) Inhibition of steryl sulfatase activity in LNCaP human prostate cancer cells. Steroids 67:821-826. (Pubitemid 35286561)
19. Stanway SJ, Purohit A, Woo LW, Sufi S, Vigushin D, Ward R, Wilson RH, Stanczyk FZ, Dobbs N, Kulinskaya E, et al. (2006) Phase I study of STX 64 (667 Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor. Clin Cancer Res 12:1585-1592.
20. Suzuki H, Kneller MB, Haining RL, Trager WF, and Rettie AE (2002) (+)-N-3-benzyl-nirvanol and (-)-N-3-benzyl-phenobarbital: new potent and selective in vitro inhibitors of CYP2C19. Drug Metab Dispos 30:235-239. (Pubitemid 34175012)
21. Tassaneeyakul W, Guo LQ, Fukuda K, Ohta T, and Yamazoe Y (2000) Inhibition selectivity of grapefruit juice components on human cytochromes P450. Arch Biochem Biophys 378:356-363. (Pubitemid 30397636)
22. Woo LL, Purohit A, Malini B, Reed MJ, and Potter BV (2000) Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates. Chem Biol 7:773-791.