A-ring modified steroidal azoles retaining similar potent and slowly reversible CYP17A1 inhibition as abiraterone

Journal of Steroid Biochemistry and Molecular Biology

Volumn 143, Issue , 2014, Pages 1-10

  Garrido, Mariana ^a   Peng, Hwei Ming ^b   Yoshimoto, Francis K ^b   Upadhyay, Sunil K ^b   Bratoeff, Eugene ^a   Auchus, Richard J ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

Abiraterone; Androgen; CYP17A1; Cytochrome P450; Enzymology; Prostate cancer; Steroidogenesis

Indexed keywords

17 (3 PYRIDYL) 5ALPHA ANDROSTA 16 ENE 3ALPHA 3 ONE; 17 (3 PYRIDYL) 5ALPHA ANDROSTA 16 ENE 3ALPHA OL; 17 (3 PYRIDYL)ANDROSTA 4,16 DIEN 3 ONE; 17 (3 PYRIDYL)ANDROSTA 4,16 DIEN 3ALPHA OL; 17 IODOANDROSTA 4,16 DIEN 3 ONE; 17 IODOANDROSTA 4,16 DIEN 3ALPHA OL; 17 IODOANDROSTA 5,16 DIEN 3BETA OL; 3ALPHA ACETOXY 17 (3 PYRIDYL) 5ALPHA ANDROSTA 16 ENE TRIFLUOROMETHANESULFONATE; 3ALPHA ACETOXY 5ALPHA ANDROSTA 16 ENE 17 YL TRIFLUOROMETHANESULFONATE; ABIRATERONE ACETATE; KETOCONAZOLE; PROGESTERONE; PYRROLE DERIVATIVE; STEROID 17ALPHA MONOOXYGENASE; UNCLASSIFIED DRUG; ABIRATERONE; ANDROSTANE DERIVATIVE; CYP17A1 PROTEIN, HUMAN; ENZYME INHIBITOR; STEROID;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DISSOCIATION; DRUG BINDING; DRUG DETERMINATION; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MICROSOME; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; YEAST; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; STRUCTURE ACTIVITY RELATION;

ANDROSTENES; ANDROSTENOLS; AZOLES; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; STEROID 17-ALPHA-HYDROXYLASE; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84896108405     PISSN: 09600760     EISSN: 18791220     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2014.01.013     Document Type: Article

References (11)

1. C. Huggins Effect of orchiectomy and irradiation on cancer of the prostate Ann. Surg. 115 1942 1192 1200
2. D.L. Trump, K.H. Havlin, E.M. Messing, K.B. Cummings, P.H. Lange, and V.C. Jordan High-dose ketoconazole in advanced hormone-refractory prostate cancer: endocrinologic and clinical effects J. Clin. Oncol. 7 1989 1093 1098 (Pubitemid 19196533)
3. W.L. Miller, and R.J. Auchus The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders Endocr. Rev. 32 2011 81 151
4. G. Attard, A.H. Reid, T.A. Yap, F. Raynaud, M. Dowsett, S. Settatree, M. Barrett, C. Parker, V. Martins, E. Folkerd, J. Clark, C.S. Cooper, S.B. Kaye, D. Dearnaley, G. Lee, and J.S. de Bono Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven J. Clin. Oncol. 26 2008 4563 4571
5. E.A. Mostaghel, and P.S. Nelson Intracrine androgen metabolism in prostate cancer progression: mechanisms of castration resistance and therapeutic implications Best Pract. Res. Clin. Endocrinol. Metab. 22 2008 243 258 (Pubitemid 351611949)
6. G.A. Potter, S.E. Barrie, M. Jarman, and M.G. Rowlands Novel steroidal inhibitors of human cytochrome P45017α (17α-hydroxylase-C17,20- lyase): potential agents for the treatment of prostatic cancer J. Med. Chem. 38 1995 2463 2471
7. N.M. DeVore, and E.E. Scott Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001 Nature 482 2012 116 119
8. 5 on CYP2E1 and CYP2C19 activities requires anionic residues D58 and D65 Biochemistry 52 2013 210 220
9. R. Li, K. Evaul, K.K. Sharma, K.H. Chang, J. Yoshimoto, J. Liu, R.J. Auchus, and N. Sharifi Abiraterone inhibits 3β-hydroxysteroid dehydrogenase: a rationale for increasing drug exposure in castration-resistant prostate cancer Clin. Cancer Res. 18 2012 3571 3579
10. D.P. Sherbet, D. Tiosano, K.M. Kwist, Z. Hochberg, and R.J. Auchus CYP17 mutation E305G causes isolated 17,20-lyase deficiency by selectively altering substrate binding J. Biol. Chem. 278 2003 48563 48569 (Pubitemid 41079494)
11. 21 steroids are substrates for human cytochrome P450c17 Arch. Biochem. Biophys. 418 2003 151 160 (Pubitemid 37159381)