سیپروترون استات

سیپروترون استات
نام‌گذاری آیوپاک
	(2aR,3aS,3bS,3cS,5aS,6R,8aS,8bR)-6-acetyl-10-chloro-3b,5a-dimethyl-2-oxo-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-6-yl acetate
اطلاعات درمانی
نام تجاری	Androcur, Androcur Depot, Cyprostat, Siterone, others
AHFS/دراگز	Micromedex Detailed Consumer Information
ردهٔ بارداری	X;
وضعیت قانونی	℞ (Prescription only);
روش مصرف دارو	خوراکی، تزریق عضلانی
اطلاعات فارماکوکینتیک
فراهمی زیستی	خوراکی: ۶۸–۱۰۰٪[1][2]
پیوند پروتئینی	آلبومین (دارو): ۹۳٪; آزاد: ۷٪[3][4][5][6]
سوخت و ساز	کبد (CYP3A4)[7][8]
متابولیت‌ها	• 15β-OH-CPA (عمده)[1][9]; • سیپروترون (جزئی)[10]; • استیک اسید (جزئی)[10]
نیمه‌عمر (داروشناسی)	خوراکی: ۱٫۶–۴٫۳ روز[10][11][12]; IM: ۳–۴٫۳ روز[2][10][12]
دفع	مدفوع: ۷۰٪[10]; ادرار: ۳۰٪[10]
شناسه‌ها
سی‌ای‌اس	427-51-0 ; 2098-66-0 (سیپروترون)
ای‌تی‌سی	G03HA01
پاب‌کم	CID: 9880
IUPHAR/BPS	2865
دراگ‌بنک	DB04839
کم‌اسپایدر	9496
UNII	4KM2BN5JHF
KEGG	D01368
ChEBI	CHEBI:50743
ChEMBL	CHEMBL139835
مترادفs	SH-80714; SH-714; NSC-81430; 1α,2α-Methylene-6-chloro-17α-hydroxy-δ6-progesterone acetate; 1α,2α-Methylene-6-chloro-17α-hydroxypregna-4,6-diene-3,20-dione acetate
اطلاعات شیمیایی
فرمول شیمیایی	C24H29ClO4
وزن مولکولی	۴۱۶٫۹۴ g·mol−1
	شناسه شیمیایی بین‌المللی InChI=1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1 ; Key:UWFYSQMTEOIJJG-FDTZYFLXSA-N ;
اطلاعات فیزیکی
دمای ذوب	۲۰۰ تا ۲۰۱ درجه سلسیوس (۳۹۲ تا ۳۹۴ درجه فارنهایت)
(بررسی)

سیپروترون استات (به انگلیسی: Cyproterone acetate) (CPA)، به تنهایی با نام تجاری Androcur یا با اتینیل‌استرادیول با نام‌های تجاری Diane یا Diane-35 و دیگر نام‌ها فروخته می‌شود، یک داروی ضدآندروژن و پروژستین است که در درمان شرایط وابسته به آندروژن مانند آکنه، رشد بیش از حد مو، بلوغ زودرس، سرطان پروستات و به عنوان مولفه‌ای در هورمون‌درمانی زنانه‌سازی برای زنان تراجنسی، و همچنین در قرص‌های ضدبارداری خوراکی استفاده می‌شود.[13][14][15][16][17] این ماده به تنهایی یا در ترکیب با استروژن فرموله و استفاده می‌شود و برای استفاده به صورت خوراکی در دسترس است. CPA روزانه یک تا سه بار و به شکل خوراکی مصرف می‌شود.

سنتز

روش‌هایی جهت سنتز شیمیایی CPA ابداع شده‌است.[18][19][20] در زیر یکی از این روش‌های سنتز آورده شده‌است:[21][22]

سنتز جزئی CPA، با استفاده از هیدروکسی‌پروژسترون استات به عنوان ماده اولیه، توسط Wiechert & Neumann (1965) و Wiechert (1966).[21][22]

منابع

Huber J, Zeillinger R, Schmidt J, Täuber U, Kuhnz W, Spona J (November 1988). "Pharmacokinetics of cyproterone acetate and its main metabolite 15 beta-hydroxy-cyproterone acetate in young healthy women". Int J Clin Pharmacol Ther Toxicol. 26 (11): 555–61. PMID 2977383.
Bińkowska M, Woroń J (June 2015). "Progestogens in menopausal hormone therapy". Przegla̜d Menopauzalny = Menopause Review. 14 (2): 134–43. doi:10.5114/pm.2015.52154. PMC 4498031. PMID 26327902.
Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins" (PDF). Maturitas. 46 Suppl 1: S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641. Since there is no binding of CPA to SHBG and CBG in the serum, 93% of the compound is bound to serum albumin.
Wakelin, Sarah H.; Maibach, Howard I.; Archer, Clive B. (1 June 2002). Systemic Drug Treatment in Dermatology: A Handbook. CRC Press. pp. 32–. ISBN 978-1-84076-013-2. It is almost exclusively bound to plasma albumin.
Hammond GL, Lähteenmäki PL, Lähteenmäki P, Luukkainen T (October 1982). "Distribution and percentages of non-protein bound contraceptive steroids in human serum". Journal of Steroid Biochemistry. 17 (4): 375–80. doi:10.1016/0022-4731(82)90629-X. PMID 6215538.
Dickman, Andrew (27 September 2012). Drugs in Palliative Care. OUP Oxford. pp. 137–138. ISBN 978-0-19-966039-1.
Boarder, Michael; Newby, David; Navti, Phyllis (25 March 2010). Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach. OUP Oxford. pp. 632–. ISBN 978-0-19-955982-4.
Frith RG, Phillipou G (1985). "15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine". J. Chromatogr. 338 (1): 179–86. doi:10.1016/0378-4347(85)80082-7. PMID 3160716.
Georg F. Weber (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 316–. ISBN 978-3-319-13278-5. The terminal half-life is about 38 h. A portion of the drug is metabolized by hydrolysis to cyproterone and acetic acid. However, in contrast to many other steroid esters hydrolysis is not extensive, and much of the pharmacological activity is exerted by the acetate form. Excretion is about 70% in the feces, mainly in the form of glucuronidated metabolites, and about 30% in the urine, predominantly as non-conjugated metabolites.
AAPL Newsletter (PDF). The Academy. 1998. CPA is 100% bioavailable when taken orally with a half life of 38 hours. The injectable form reaches maximum plasma levels in 82 hours and has a half life of about 72 hours.
Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
Barradell LB, Faulds D (July 1994). "Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer". Drugs Aging. 5 (1): 59–80. doi:10.2165/00002512-199405010-00006. PMID 7919640.
Neumann F (1994). "The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research". Exp. Clin. Endocrinol. 102 (1): 1–32. doi:10.1055/s-0029-1211261. PMID 8005205.
Neumann F (January 1977). "Pharmacology and potential use of cyproterone acetate". Horm. Metab. Res. 9 (1): 1–13. doi:10.1055/s-0028-1093574. PMID 66176.
Neumann F, Töpert M (November 1986). "Pharmacology of antiandrogens". Journal of Steroid Biochemistry. 25 (5B): 885–95. doi:10.1016/0022-4731(86)90320-1. PMID 2949114.
Jürgen Engel; Axel Kleemann; Bernhard Kutscher; Dietmar Reichert (14 May 2014). Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. Thieme. pp. 351–352. ISBN 978-3-13-179275-4.
William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1182–1183. ISBN 978-0-8155-1856-3.
Duang Buddhasukh, Roland Maier, Aranya Manosroi, Jiradej Manosroi, Pattana Sripalakit, Rolf Werner (29 April 2002). "EP1359154A1 Further syntheses of cyproterone acetate". Google Patents.
"Verfahren zur Herstellung von 1, 2alpha-Methylen-delta-17alpha-hydroxy-progesteronen"."Verfahren zur Herstellung von 1, 2alpha-Methylen-delta-17alpha-hydroxy-progesteronen".
"6-chloro-1, 2alpha-methylene-delta6-17alpha-hydroxyprogesterone compounds and compositions"."6-chloro-1, 2alpha-methylene-delta6-17alpha-hydroxyprogesterone compounds and compositions".

مطالعه بیشتر

Neumann F (1971). "Use of cyproterone acetate in animal and clinical trials". Gynecol Invest. 2 (1): 150–79. doi:10.1159/000301860. PMID 4949823.
Neumann, F.; Steinbeck, H. (1974). Androgens II and Antiandrogens / Androgene II und Antiandrogene. pp. 235–484. doi:10.1007/978-3-642-80859-3_6. ISBN 978-3-642-80861-6.
Gräf, K. -J.; Brotherton, J.; Neumann, F. (1974). Androgens II and Antiandrogens / Androgene II und Antiandrogene. pp. 485–542. doi:10.1007/978-3-642-80859-3_7. ISBN 978-3-642-80861-6.
Horn, H. J. (1974). "Administration of Antiandrogens in Hypersexuality and Sexual Deviations". Androgens II and Antiandrogens / Androgene II und Antiandrogene. pp. 543–562. doi:10.1007/978-3-642-80859-3_8. ISBN 978-3-642-80861-6.
Hammerstein J, Meckies J, Leo-Rossberg I, Moltz L, Zielske F (June 1975). "Use of cyproterone acetate (CPA) in the treatment of acne, hirsutism and virilism". J. Steroid Biochem. 6 (6): 827–36. doi:10.1016/0022-4731(75)90311-8. PMID 126335.
Neumann F (January 1977). "Pharmacology and potential use of cyproterone acetate". Horm. Metab. Res. 9 (1): 1–13. doi:10.1055/s-0028-1093574. PMID 66176.
Neumann F (July 1983). "Pharmacological basis for clinical use of antiandrogens". Hormonal Steroids. J. Steroid Biochem. 19. pp. 391–402. doi:10.1016/B978-0-08-030771-8.50055-3. ISBN 9780080307718. PMID 6224971.
Hammerstein J, Moltz L, Schwartz U (July 1983). "Antiandrogens in the treatment of acne and hirsutism". J. Steroid Biochem. 19 (1B): 591–7. doi:10.1016/0022-4731(83)90223-6. PMID 6224974.
Miller JA, Jacobs HS (May 1986). "Treatment of hirsutism and acne with cyproterone acetate". Clin Endocrinol Metab. 15 (2): 373–89. doi:10.1016/S0300-595X(86)80031-7. PMID 2941191.
Neumann F, Wiechert R (March 1988). "Das Antiandrogen Cyproteronacetat: Seine Geschichte von der Entdeckung bis zur Marktreife" [The Antiandrogen Cyproterone Acetate: Its History from Discovery to Marketing]. Pharm Unserer Zeit (به آلمانی). 17 (2): 33–50. doi:10.1002/pauz.19880170202. PMID 2967500.
Tunn UW (1989). "Cyproterone acetate in the management of prostatic cancer". Prog. Clin. Biol. Res. 303: 105–10. PMID 2528734.
Hammerstein, J. (1990). "Antiandrogens: Clinical Aspects". Hair and Hair Diseases. pp. 827–886. doi:10.1007/978-3-642-74612-3_35. ISBN 978-3-642-74614-7.
Mowszowicz I (January 1989). "Les antiandrogènes. Mécanismes et effets paradoxaux" [Antiandrogens. Mechanisms and paradoxical effects]. Annales d'Endocrinologie (Paris) (به فرانسوی). 50 (3): 189–99. ISSN 0003-4266. PMID 2530930.
Schindler AE (October 1990). "[Anti-androgen therapy in the female]". Geburtshilfe Frauenheilkd (به آلمانی). 50 (10): 749–53. doi:10.1055/s-2008-1026359. PMID 1704865.
de Voogt HJ (1990). "Cyproterone acetate as monotherapy in prospective randomized trials". Prog. Clin. Biol. Res. 359: 85–91, discussion 105–7. PMID 2149459.
Namer M (October 1988). "Clinical applications of antiandrogens". J. Steroid Biochem. 31 (4B): 719–29. doi:10.1016/0022-4731(88)90023-4. PMID 2462132.
Goldenberg SL, Bruchovsky N (1991). "Use of cyproterone acetate in prostate cancer". Urol. Clin. North Am. 18 (1): 111–22. PMID 1825143.
Neumann F, Kalmus J (1991). "Cyproterone acetate in the treatment of sexual disorders: pharmacological base and clinical experience". Exp. Clin. Endocrinol. 98 (2): 71–80. doi:10.1055/s-0029-1211103. PMID 1838080.
de Voogt HJ (1992). "The position of cyproterone acetate (CPA), a steroidal anti-androgen, in the treatment of prostate cancer". Prostate Suppl. 4: 91–5. doi:10.1002/pros.2990210514. PMID 1533452. S2CID 22747185.
Schröder FH (1993). "Cyproterone acetate--mechanism of action and clinical effectiveness in prostate cancer treatment". Cancer. 72 (12 Suppl): 3810–5. doi:10.1002/1097-0142(19931215)72:12+<3810::aid-cncr2820721710>3.0.co;2-o. PMID 8252496.
Barradell LB, Faulds D (1994). "Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer". Drugs Aging. 5 (1): 59–80. doi:10.2165/00002512-199405010-00006. PMID 7919640.
Neumann F (1994). "The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research" (PDF). Exp. Clin. Endocrinol. 102 (1): 1–32. doi:10.1055/s-0029-1211261. PMID 8005205.
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Diamanti-Kandarakis E (October 1998). "How actual is the treatment with antiandrogen alone in patients with polycystic ovary syndrome?". J. Endocrinol. Invest. 21 (9): 623–9. doi:10.1007/BF03350788. PMID 9856417. S2CID 46484837.
Diamanti-Kandarakis E (September 1999). "Current aspects of antiandrogen therapy in women". Curr. Pharm. Des. 5 (9): 707–23. PMID 10495361.
Migliari R, Muscas G, Murru M, Verdacchi T, De Benedetto G, De Angelis M (December 1999). "Antiandrogens: a summary review of pharmacodynamic properties and tolerability in prostate cancer therapy". Arch Ital Urol Androl. 71 (5): 293–302. PMID 10673793.
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Reilly DR, Delva NJ, Hudson RW (August 2000). "Protocols for the use of cyproterone, medroxyprogesterone, and leuprolide in the treatment of paraphilia". Can J Psychiatry. 45 (6): 559–63. doi:10.1177/070674370004500608. PMID 10986575.
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[pmid2977383-2] Huber J, Zeillinger R, Schmidt J, Täuber U, Kuhnz W, Spona J (November 1988). "Pharmacokinetics of cyproterone acetate and its main metabolite 15 beta-hydroxy-cyproterone acetate in young healthy women". Int J Clin Pharmacol Ther Toxicol. 26 (11): 555–61. PMID 2977383.

[BińkowskaWoroń2015-3] Bińkowska M, Woroń J (June 2015). "Progestogens in menopausal hormone therapy". Przegla̜d Menopauzalny = Menopause Review. 14 (2): 134–43. doi:10.5114/pm.2015.52154. PMC 4498031. PMID 26327902.

[SchindlerCampagnoli2003-4] Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins" (PDF). Maturitas. 46 Suppl 1: S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641. Since there is no binding of CPA to SHBG and CBG in the serum, 93% of the compound is bound to serum albumin.

[WakelinMaibach2002-5] Wakelin, Sarah H.; Maibach, Howard I.; Archer, Clive B. (1 June 2002). Systemic Drug Treatment in Dermatology: A Handbook. CRC Press. pp. 32–. ISBN 978-1-84076-013-2. It is almost exclusively bound to plasma albumin.

[HammondLähteenmäki1982-6] Hammond GL, Lähteenmäki PL, Lähteenmäki P, Luukkainen T (October 1982). "Distribution and percentages of non-protein bound contraceptive steroids in human serum". Journal of Steroid Biochemistry. 17 (4): 375–80. doi:10.1016/0022-4731(82)90629-X. PMID 6215538.

[Dickman2012-7] Dickman, Andrew (27 September 2012). Drugs in Palliative Care. OUP Oxford. pp. 137–138. ISBN 978-0-19-966039-1.

[BoarderNewby2010-8] Boarder, Michael; Newby, David; Navti, Phyllis (25 March 2010). Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach. OUP Oxford. pp. 632–. ISBN 978-0-19-955982-4.

[pmid3160716-9] Frith RG, Phillipou G (1985). "15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine". J. Chromatogr. 338 (1): 179–86. doi:10.1016/0378-4347(85)80082-7. PMID 3160716.

[Weber2015-10] Georg F. Weber (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 316–. ISBN 978-3-319-13278-5. The terminal half-life is about 38 h. A portion of the drug is metabolized by hydrolysis to cyproterone and acetic acid. However, in contrast to many other steroid esters hydrolysis is not extensive, and much of the pharmacological activity is exerted by the acetate form. Excretion is about 70% in the feces, mainly in the form of glucuronidated metabolites, and about 30% in the urine, predominantly as non-conjugated metabolites.

[BradfordKaye1998-12] AAPL Newsletter (PDF). The Academy. 1998. CPA is 100% bioavailable when taken orally with a half life of 38 hours. The injectable form reaches maximum plasma levels in 82 hours and has a half life of about 72 hours.

[pmid_16112947-13] Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.

[pmid_7919640-14] Barradell LB, Faulds D (July 1994). "Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer". Drugs Aging. 5 (1): 59–80. doi:10.2165/00002512-199405010-00006. PMID 7919640.

[pmid_8005205-15] Neumann F (1994). "The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research". Exp. Clin. Endocrinol. 102 (1): 1–32. doi:10.1055/s-0029-1211261. PMID 8005205.

[pmid_66176-16] Neumann F (January 1977). "Pharmacology and potential use of cyproterone acetate". Horm. Metab. Res. 9 (1): 1–13. doi:10.1055/s-0028-1093574. PMID 66176.

[pmid_2949114-17] Neumann F, Töpert M (November 1986). "Pharmacology of antiandrogens". Journal of Steroid Biochemistry. 25 (5B): 885–95. doi:10.1016/0022-4731(86)90320-1. PMID 2949114.

[EngelKleemann20142-18] Jürgen Engel; Axel Kleemann; Bernhard Kutscher; Dietmar Reichert (14 May 2014). Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. Thieme. pp. 351–352. ISBN 978-3-13-179275-4.

[Publishing20132-19] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1182–1183. ISBN 978-0-8155-1856-3.

[20] Duang Buddhasukh, Roland Maier, Aranya Manosroi, Jiradej Manosroi, Pattana Sripalakit, Rolf Werner (29 April 2002). "EP1359154A1 Further syntheses of cyproterone acetate". Google Patents.

[DE1189991B-21] "Verfahren zur Herstellung von 1, 2alpha-Methylen-delta-17alpha-hydroxy-progesteronen"."Verfahren zur Herstellung von 1, 2alpha-Methylen-delta-17alpha-hydroxy-progesteronen".

[US3234093A-22] "6-chloro-1, 2alpha-methylene-delta6-17alpha-hydroxyprogesterone compounds and compositions"."6-chloro-1, 2alpha-methylene-delta6-17alpha-hydroxyprogesterone compounds and compositions".