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Abiraterone Acetate

Description of abiraterone acetate: Abiraterone acetate is an FDA approved drug, and is an orally active acetate ester of the steroidal compound abiraterone with antiandrogen activity. Abiraterone acetate was approved by the U.S. Food and Drug Administration (FDA) in April 2011. Abiraterone inhibits the enzymatic activity of steroid 17alpha-monooxygenase (17alpha-hydrolase/C17,20 lyase complex), a member of the cytochrome p450 family that catalyzes the 17alpha-hydroxylation of steroid intermediates involved in testosterone synthesis. Administration of this agent may suppress testosterone production by both the testes and the adrenals to castrate-range levels. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Current developer:  Cougar Biotechnology Inc, and Johnson & Johnson。

ZYTIGA™ (abiraterone acetate) received FDA Approval  in May 2011 for Treatment of Metastatic Prostate Cancer After Priority Review; First Once-Daily, Oral Treatment for Metastatic Prostate Cancer Inhibits Androgen Production. ZYTIGA^™ (abiraterone acetate) in combination with prednisone is indicated for the treatment of patients with metastatic castration-resistant prostate cancer (CRPC) who have received prior chemotherapy containing docetaxel.

According to Wikipedia, Abiraterone (tradename Zytiga) is a drug currently under investigation for use in castration-resistant prostate cancer (formerly hormone-resistant or hormone-refractory prostate cancer) (prostate cancer not responding to androgen deprivation or treatment with antiandrogens). After an expedited six-month review, the drug has been approved for use by the Food and Drug Administration (FDA). This drug was initially discovered in the Cancer Research UK Centre for Cancer Therapeutics at the Institute of Cancer Research in London. Rights for commercialization of the drug were assigned to BTG plc, a UK company that manages commercialization activity in pharmaceuticals. BTG then licensed the product to Cougar Biotechnology which began development of the commercial product.  In 2009, Cougar was acquired by Johnson & Johnson which is currently conducting clinical trials on abiraterone.   http://en.wikipedia.org/wiki/Abiraterone).  

Chemical synthesis of Abiraterone acetate

The following synthetic route of Abiraterone acetate was  from J Med Chem. 1995 Jun 23;38(13):2463-71. Novel steroidal inhibitors of human cytochrome P45017 alpha (17 alpha-hydroxylase-C17,20-lyase): potential agents for the treatment of prostatic cancer. Potter GA, Barrie SE, Jarman M, Rowlands MG. Cancer Research Campaign Centre for Cancer Therapeutics, Institute of Cancer Research, Sutton, Surrey, U.K.

1: Sonpavde G, Attard G, Bellmunt J, Mason MD, Malavaud B, Tombal B, Sternberg CN. The Role of Abiraterone Acetate in the Management of Prostate Cancer: A Critical Analysis of the Literature. Eur Urol. 2011 Apr 29. [Epub ahead of print] PubMed PMID: 21550166.

2: Ryan C. Abiraterone in prostate cancer. Clin Adv Hematol Oncol. 2010 Nov;8(11):761-2. PubMed PMID: 21326154.

3: Salem M, Garcia JA. Abiraterone acetate, a novel adrenal inhibitor in metastatic castration-resistant prostate cancer. Curr Oncol Rep. 2011 Apr;13(2):92-6. PubMed PMID: 21243537.

4: Schmidt C. Abiraterone and MVD3100 take androgen deprivation to a new level. J Natl Cancer Inst. 2011 Feb 2;103(3):175-6. Epub 2011 Jan 17. PubMed PMID: 21242338.

5: Mohler JL, Pantuck AJ. Use of abiraterone for prostate cancer. J Urol. 2011 Mar;185(3):783-6. Epub 2011 Jan 15. PubMed PMID: 21239011.

6: Abiraterone acetate. Drugs R D. 2010;10(4):261-9. doi: 10.2165/11587960-000000000-00000. PubMed PMID: 21171672.

7: Pal SK, Sartor O. Phase III data for abiraterone in an evolving landscape for castration-resistant prostate cancer. Maturitas. 2011 Feb;68(2):103-5. Epub 2010 Nov 19. PubMed PMID: 21093995.

8: Attard G, Reid AH, de Bono JS. Abiraterone acetate is well tolerated without concomitant use of corticosteroids. J Clin Oncol. 2010 Oct 10;28(29):e560-1; author reply e562. Epub 2010 Aug 30. PubMed PMID: 20805462.

9: Vogiatzi P, Claudio PP. Efficacy of abiraterone acetate in post-docetaxel castration-resistant prostate cancer. Expert Rev Anticancer Ther. 2010 Jul;10(7):1027-30. PubMed PMID: 20645691.

10: Agarwal N, Hutson TE, Vogelzang NJ, Sonpavde G. Abiraterone acetate: a promising drug for the treatment of castration-resistant prostate cancer. Future Oncol. 2010 May;6(5):665-79. Review. PubMed PMID: 20465382.

11: Shah S, Ryan C. Abiraterone acetate for castration resistant prostate cancer. Expert Opin Investig Drugs. 2010 Apr;19(4):563-70. Review. PubMed PMID: 20225998.

12: Ryan CJ, Smith MR, Fong L, Rosenberg JE, Kantoff P, Raynaud F, Martins V, Lee G, Kheoh T, Kim J, Molina A, Small EJ. Phase I clinical trial of the CYP17 inhibitor abiraterone acetate demonstrating clinical activity in patients with castration-resistant prostate cancer who received prior ketoconazole therapy. J Clin Oncol. 2010 Mar 20;28(9):1481-8. Epub 2010 Feb 16. PubMed PMID: 20159824; PubMed Central PMCID: PMC2849769.

13: Reid AH, Attard G, Danila DC, Oommen NB, Olmos D, Fong PC, Molife LR, Hunt J, Messiou C, Parker C, Dearnaley D, Swennenhuis JF, Terstappen LW, Lee G, Kheoh T, Molina A, Ryan CJ, Small E, Scher HI, de Bono JS. Significant and sustained antitumor activity in post-docetaxel, castration-resistant prostate cancer with the CYP17 inhibitor abiraterone acetate. J Clin Oncol. 2010 Mar 20;28(9):1489-95. Epub 2010 Feb 16. PubMed PMID: 20159823; PubMed Central PMCID: PMC2849770.

14: Danila DC, Morris MJ, de Bono JS, Ryan CJ, Denmeade SR, Smith MR, Taplin ME, Bubley GJ, Kheoh T, Haqq C, Molina A, Anand A, Koscuiszka M, Larson SM, Schwartz LH, Fleisher M, Scher HI. Phase II multicenter study of abiraterone acetate plus prednisone therapy in patients with docetaxel-treated castration-resistant prostate cancer. J Clin Oncol. 2010 Mar 20;28(9):1496-501. Epub 2010 Feb 16. PubMed PMID: 20159814; PubMed Central PMCID: PMC3040042.

15: Eisenberger MA. Words of wisdom. Re: Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven. Attard G, Reide AHM, Yap TA, Raynaud F, Dowsett M, Settatree S, Barrett M, Parker C, Martins V, Folkerd E, Clark J, Cooper C, Kaye S, Dearnaley D, Lee G, de Bono JS. J Clin Oncol 2008;26:4563-71. Eur Urol. 2009 Jan;55(1):248. PubMed PMID: 20050017.

16: Schmid HP, Engeler DS. Words of wisdom. Re: Selective inhibition of CYP17 with abiraterone acetate is highly active in the treatment of castration-resistant prostate cancer. Eur Urol. 2009 Oct;56(4):744-5. PubMed PMID: 19995526.

17: Vogelzang NJ. Words of wisdom. Re: Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven. Attard G, Reid AH, Yap TA, et al. J Clin Oncol 2008;26:4563-71. Eur Urol. 2009 Jul;56(1):220. PubMed PMID: 19995520.

18: Attard G, Reid AH, A'Hern R, Parker C, Oommen NB, Folkerd E, Messiou C, Molife LR, Maier G, Thompson E, Olmos D, Sinha R, Lee G, Dowsett M, Kaye SB, Dearnaley D, Kheoh T, Molina A, de Bono JS. Selective inhibition of CYP17 with abiraterone acetate is highly active in the treatment of castration-resistant prostate cancer. J Clin Oncol. 2009 Aug 10;27(23):3742-8. Epub 2009 May 26. PubMed PMID: 19470933.

19: Ang JE, Olmos D, de Bono JS. CYP17 blockade by abiraterone: further evidence for frequent continued hormone-dependence in castration-resistant prostate cancer. Br J Cancer. 2009 Mar 10;100(5):671-5. Epub 2009 Feb 17. Review. PubMed PMID: 19223900; PubMed Central PMCID: PMC2653756.

20: Schalken JA. Words of wisdom. Re: phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration- resistant prostate cancer commonly remains hormone driven. Eur Urol. 2008 Dec;54(6):1438-9. PubMed PMID: 19189435.

21: Antonarakis ES, Eisenberger MA. Is abiraterone acetate well tolerated and effective in the treatment of castration-resistant prostate cancer? Nat Clin Pract Oncol. 2009 Jan;6(1):12-3. Epub 2008 Oct 28. PubMed PMID: 18957947.

22: Pinto-Bazurco Mendieta MA, Negri M, Jagusch C, Müller-Vieira U, Lauterbach T, Hartmann RW. Synthesis, biological evaluation, and molecular modeling of abiraterone analogues: novel CYP17 inhibitors for the treatment of prostate cancer. J Med Chem. 2008 Aug 28;51(16):5009-18. Epub 2008 Aug 2. PubMed PMID: 18672868.

23: Attard G, Reid AH, Yap TA, Raynaud F, Dowsett M, Settatree S, Barrett M, Parker C, Martins V, Folkerd E, Clark J, Cooper CS, Kaye SB, Dearnaley D, Lee G, de Bono JS. 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. 2008 Oct 1;26(28):4563-71. Epub 2008 Jul 21. PubMed PMID: 18645193.

24: Martins V, Asad Y, Wilsher N, Raynaud F. A validated liquid chromatographic-tandem mass spectroscopy method for the quantification of abiraterone acetate and abiraterone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Nov 7;843(2):262-7. Epub 2006 Jun 30. PubMed PMID: 16809076.

25: Madan RA, Arlen PM. Abiraterone. Cougar Biotechnology. IDrugs. 2006 Jan;9(1):49-55. PubMed PMID: 16374734.

26: O'Donnell A, Judson I, Dowsett M, Raynaud F, Dearnaley D, Mason M, Harland S, Robbins A, Halbert G, Nutley B, Jarman M. Hormonal impact of the 17alpha-hydroxylase/C(17,20)-lyase inhibitor abiraterone acetate (CB7630) in patients with prostate cancer. Br J Cancer. 2004 Jun 14;90(12):2317-25. PubMed PMID: 15150570; PubMed Central PMCID: PMC2409523.

27: Jarman M, Barrie SE, Llera JM. The 16,17-double bond is needed for irreversible inhibition of human cytochrome p45017alpha by abiraterone (17-(3-pyridyl)androsta-5, 16-dien-3beta-ol) and related steroidal inhibitors. J Med Chem. 1998 Dec 31;41(27):5375-81. PubMed PMID: 9876107.

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