Product Name

Cyproterone Acetate

CAS Number

427-51-0

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Product Name:
Cyproterone Acetate
CAS Number:
427-51-0
Indication:
For the palliative treatment of patients with advanced prostatic carcinoma.
Mode of Action:

The direct antiandrogenic effect of cyproterone is blockage of the binding of dihydrotestosterone to the specific receptors in the prostatic carcinoma cell. In addition, cyproterone exerts a negative feed-back on the hypothalamo-pituitary axis, by inhibiting the secretion of luteinizing hormone resulting in diminished production of testicular testosterone.

Pharmacodynamics:

Cyproterone is an antiandrogen. 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).

Metabolism:

Primarily hepatic. Cyproterone acetate is metabolized by the CYP3A4 enzyme, forming the active metabolite 15beta-hydroxycyproterone acetate, which retains its antiandrogen activity, but has reduced progestational activity.

IUPAC:
(1S, 2S, 3S, 5R, 11R, 12S, 15R, 16S)-15-acetyl-9-chloro-2, 16-dimethyl-6-oxopentacyclo[9.7.0.0², ⁸.0³, ⁵.0¹², ¹⁶]octadeca-7, 9-dien-15-yl acetate
ATC:
G03HA01
PubChem:
5284537
Formula:
C24H29ClO4
Molecular Mass:
416.938
SMILES:
[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](OC(C)=O)(C(C)=O)[C@@]3(C)CC[C@]12[H]
InChi:
InChI=1/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-/s2
General Reference:
General Reference:

 

  1. Giorgi EP, Shirley IM, Grant JK, Stewart JC: Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate. Biochem J. 1973 Mar;132(3):465-74. Pubmed
  2. Pham-Huu-Trung MT, de Smitter N, Bogyo A, Girard F: Effects of cyproterone acetate on adrenal steroidogenesis in vitro. Horm Res. 1984;20(2):108-15. Pubmed
  3. Stadtler FA, Langner V: The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study. Pathol Res Pract. 1985 Mar;179(4-5):493-8. Pubmed
  4. Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, Cornell W, Steele R, Schweitzer R, Schumacher C: Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol Pharmacol. 2003 May;63(5):1012-20. Pubmed
  5. Holdaway IM, Croxson MS, Evans MC, France J, Sheehan A, Wilson T, Ibbertson HK: Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism. Acta Endocrinol (Copenh). 1983 Oct;104(2):222-6. Pubmed

 

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