Synonym
Cyprostat; Cyproteron; Procur; Cyprone; Cyprohexal; Ciproterona; Cyproteronum; Neoproxil; Siterone; SH 714; SH714; SH-714; Androcur; Cyproviron; Cyprostat; CPA; NSC 81430; NSC-81430; NSC81430;
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
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
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 |
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.