Cyproterone acetate | CAS#427-51-0 | antiandrogen

Cyproterone acetate
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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.

Chemical Structure

Cyproterone acetate

CAS# 427-51-0

Instruction

Theoretical Analysis

MedKoo Cat#: 315338
Name: Cyproterone acetate
CAS#: 427-51-0
Chemical Formula: C24H29ClO4
Exact Mass: 416.18
Molecular Weight: 416.938
Elemental Analysis: C, 69.14; H, 7.01; Cl, 8.50; O, 15.35

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 450
500mg	USD 650
1g	USD 950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 416.94 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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

2: Mothes C. Cyproterone acetate. Lancet. 1976 Nov 6;2(7993):1020. doi: 10.1016/s0140-6736(76)90851-5. PMID: 62231.

3: Pinganaud G, Chaslerie A, Bourdel Marchasson I, Decamps A, Manciet G, Emeriau JP. Cyproterone-induced hepatotoxicity. Ann Pharmacother. 1995 Jun;29(6):634. doi: 10.1177/106002809502900619. PMID: 7663042.

4: de Voogt HJ. Cyproterone acetate as monotherapy in prospective randomized trials. Prog Clin Biol Res. 1990;359:85-91; discussion 105-7. PMID: 2149459.

5: Goldenberg SL, Bruchovsky N. Use of cyproterone acetate in prostate cancer. Urol Clin North Am. 1991 Feb;18(1):111-22. PMID: 1825143.

6: Paulsen CA. Letter: Cyproterone acetate. Lancet. 1976 Jun 5;1(7971):1246. PMID: 58294.

7: Neumann F, Kalmus J. Cyproterone acetate in the treatment of sexual disorders: pharmacological base and clinical experience. Exp Clin Endocrinol. 1991;98(2):71-80. doi: 10.1055/s-0029-1211103. PMID: 1838080.

8: Neumann F, Wiechert R. Das Antiandrogen Cyproteronacetat. Seine Geschichte von der Entdeckung bis zur Marktreife [The antiandrogen cyproterone acetate. Its history from discovery to marketing]. Pharm Unserer Zeit. 1988 Mar;17(2):33-50. German. doi: 10.1002/pauz.19880170202. PMID: 2967500.

9: Chapman MG, Jeffcoate SL, Dewhurst J. Cyproterone acetate and adrenosuppression. Lancet. 1981 Aug 22;2(8243):417. doi: 10.1016/s0140-6736(81)90853-9. PMID: 6115178.

10: Tunn UW. Cyproterone acetate in the management of prostatic cancer. Prog Clin Biol Res. 1989;303:105-10. PMID: 2528734.

11: de Voogt HJ. The position of cyproterone acetate (CPA), a steroidal anti- androgen, in the treatment of prostate cancer. Prostate Suppl. 1992;4:91-5. doi: 10.1002/pros.2990210514. PMID: 1533452.

12: Miller JA, Jacobs HS. Treatment of hirsutism and acne with cyproterone acetate. Clin Endocrinol Metab. 1986 May;15(2):373-89. doi: 10.1016/s0300-595x(86)80031-7. PMID: 2941191.

13: Greenwood R, Burke B, Brummitt L, Cunliffe WJ. Cyclic cyproterone/ethinyloestradiol for acne. Lancet. 1983 Oct 1;2(8353):796. doi: 10.1016/s0140-6736(83)92331-0. PMID: 6137631.

14: Cooper AJ, Cernovovsky Z. The effects of cyproterone acetate on sleeping and waking penile erections in pedophiles: possible implications for treatment. Can J Psychiatry. 1992 Feb;37(1):33-9. doi: 10.1177/070674379203700108. PMID: 1532338.

15: Davies TS. Cyproterone acetate for male hypersexuality. J Int Med Res. 1974;2(2):159-63. doi: 10.1177/030006057400200211. PMID: 4468912.

16: von Mühlendahl KE, Korth-Schütz S, Müller-Hess R, Helge H, Weber B. Cyproterone acetate and adrenocortical function. Lancet. 1977 May 28;1(8022):1160-1. doi: 10.1016/s0140-6736(77)92426-6. PMID: 68264.

17: Schuppler J, Günzel P. Letter: Cyproterone acetate. Lancet. 1976 Sep 25;2(7987):688. doi: 10.1016/s0140-6736(76)92498-3. PMID: 60545.

18: Byrne A, Brunet B, McGann P. Cyproterone acetate therapy and aggression. Br J Psychiatry. 1992 Feb;160:282-3. doi: 10.1192/bjp.160.2.282. PMID: 1531776.

19: Bercovici JP. Acétate de cyprotérone [Cyproterone acetate]. Ann Endocrinol (Paris). 1983;44(6):385. French. PMID: 6234848.

20: Kauli R, Pertzelan A, Prager-Lewin R, Grünebaum M, Laron Z. Cyproterone acetate in treatment of precocious puberty. Arch Dis Child. 1976 Mar;51(3):202-8. doi: 10.1136/adc.51.3.202. PMID: 952553; PMCID: PMC1545909.

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