WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 315338
CAS#: 427-51-0
Description: Cyproterone acetate is an antiandrogen, i.e. it suppresses the actions of testosterone (and its metabolite dihydrotestosterone) on tissues. It acts by blocking androgen receptors which prevents androgens from binding to them and suppresses luteinizing hormone (which in turn reduces testosterone levels). Its main indications are prostate cancer, benign prostatic hyperplasia, priapism, hypersexuality and other conditions in which androgen action maintains the disease process. Due to its anti-androgen effect, it can also be used to treat hirsutism, and is a common component in hormone therapy for male-to-female transsexual people.
MedKoo Cat#: 315338
Name: Cyproterone acetate
CAS#: 427-51-0
Chemical Formula: C24H29ClO4
Exact Mass: 416.17544
Molecular Weight: 416.93766
Elemental Analysis: C, 69.14; H, 7.01; Cl, 8.50; O, 15.35
Synonym: Androcur, Cyprostat,Cyproteron, Procur, Cyprone, Cyprohexal, Ciproterona, Cyproteronum, Neoproxil, Siterone.
IUPAC/Chemical Name: (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
InChi Key: UWFYSQMTEOIJJG-FDTZYFLXSA-N
InChi Code: 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
SMILES Code: CC(O[C@]1(C(C)=O)CC[C@]2([H])[C@]1(C)CC[C@]3([H])[C@@]4(C)[C@](C5)([H])[C@]5([H])C(C=C4C(Cl)=C[C@@]23[H])=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO.
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 416.93766 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Bessone F, Isabel Lucena M, Roma MG, Stephens C, Medina-Cáliz I, Frider B, Tsariktsian G, Hernández N, Bruguera M, Gualano G, Fassio E, Montero J, Reggiardo MV, Ferretti S, Colombato L, Tanno F, Ferrer J, Zeno L, Tanno H, Andrade RJ. Cyproterone acetate induces a wide spectrum of acute liver damage including corticosteroid-responsive hepatitis: report of 22 cases. Liver Int. 2015 Jun 22. doi: 10.1111/liv.12899. [Epub ahead of print] PubMed PMID: 26104271.
2: Rime H, Nguyen T, Ombredane K, Fostier A, Bobe J. Effects of the anti-androgen cyproterone acetate (CPA) on oocyte meiotic maturation in rainbow trout (Oncorhynchus mykiss). Aquat Toxicol. 2015 Jul;164:34-42. doi: 10.1016/j.aquatox.2015.04.009. Epub 2015 Apr 9. PubMed PMID: 25911576.
3: Ding W, Bishop ME, Pearce MG, Davis KJ, White GA, Lyn-Cook LE, Manjanatha MG. Sex-specific dose-response analysis of genotoxicity in cyproterone acetate-treated F344 rats. Mutat Res Genet Toxicol Environ Mutagen. 2014 Nov 1;774:1-7. doi: 10.1016/j.mrgentox.2014.08.005. Epub 2014 Sep 3. PubMed PMID: 25440904.
4: Messina MF, Aversa T, de Sanctis L, Wasniewska M, Valenzise M, Pajno GB, De Luca F, Lombardo F. Adult height following a combined treatment of ketoconazole - cyproterone acetate - leuprolide depot in a boy with atypical McCune-Albright syndrome. Hormones (Athens). 2015 Feb;14(2):286-92. doi: 10.14310/horm.2002.1515. PubMed PMID: 25402389.
5: Leelaphiwat S, Jongwutiwes T, Lertvikool S, Tabcharoen C, Sukprasert M, Rattanasiri S, Weerakiet S. Comparison of desogestrel/ethinyl estradiol plus spironolactone versus cyproterone acetate/ethinyl estradiol in the treatment of polycystic ovary syndrome: a randomized controlled trial. J Obstet Gynaecol Res. 2015 Mar;41(3):402-10. doi: 10.1111/jog.12543. Epub 2014 Oct 15. PubMed PMID: 25319761.
6: El-Gamal OM, Gameel TA, Ghoneem A, Soliman MG, Abo-El-Enen M, El-Hitham AA, El-Rasheedy M, Elbendary MA, Sabaa M. Perioperative use of cyproterone acetate with transurethral resection of large prostate: preliminary results. J Endourol. 2015 May;29(5):569-74. doi: 10.1089/end.2014.0526. Epub 2014 Dec 22. PubMed PMID: 25316503.
7: Kim JH, Yoo BW, Yang WJ. Hepatic failure induced by cyproterone acetate: A case report and literature review. Can Urol Assoc J. 2014 May;8(5-6):E458-61. doi: 10.5489/cuaj.1753. PubMed PMID: 25024808; PubMed Central PMCID: PMC4081269.
8: Montani D, Bertoletti L, Chaumais MC, Perrin S, Fabre D, Chaouat A, Jaïs X, Simonneau G, Humbert M. Chronic thromboembolic pulmonary hypertension complicating long-term cyproterone acetate therapy. Eur Respir Rev. 2014 Jun;23(132):260-3. doi: 10.1183/09059180.00005913. PubMed PMID: 24881082.
9: Kahraman K, Sükür YE, Atabekoğlu CS, Ateş C, Taşkın S, Cetinkaya SE, Tolunay HE, Ozmen B, Sönmezer M, Berker B. Comparison of two oral contraceptive forms containing cyproterone acetate and drospirenone in the treatment of patients with polycystic ovary syndrome: a randomized clinical trial. Arch Gynecol Obstet. 2014 Aug;290(2):321-8. doi: 10.1007/s00404-014-3217-5. Epub 2014 Mar 28. PubMed PMID: 24676694.
10: Gourbil M, Grandvuillemin A, Beyens MN, Massy N, Gras V, D'Amico A, Miremont-Salamé G, Petitpain N; French Network of Regional Pharmacovigilance Centres. Thromboembolic events in women exposed to hormonal contraception or cyproterone acetate in 2012: a cross-sectional observational study in 30 French public hospitals. Drug Saf. 2014 Apr;37(4):269-82. doi: 10.1007/s40264-014-0149-8. PubMed PMID: 24634164.
