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Identification
Name Cyproterone
Accession Number DB04839
Type small molecule
Groups approved
Description

An anti-androgen that, in the form of its acetate (cyproterone acetate), also has progestational properties. It is used in the treatment of hypersexuality in males, as a palliative in prostatic carcinoma, and, in combination with estrogen, for the therapy of severe acne and hirsutism in females. [Pubchem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Cyproterone acetate
Salts Not Available
Brand names
Name Company
Androcur
Apo-cyproterone
CyPat
Gen-Cyproterone
Novo-cyproterone
Brand mixtures
Brand Name Ingredients
Diane-35 Cyproterone Acetate + Ethinyl Estradiol
Categories
  • Androgen Antagonists
CAS number 2098-66-0
Weight Average: 374.901
Monoisotopic: 374.164872437
Chemical Formula C22H27ClO3
InChI Key InChIKey=DUSHUSLJJMDGTE-ZJPMUUANSA-N
InChI
InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1
Plain Text
IUPAC Name
(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0^{2,8}.0^{3,5}.0^{12,16}]octadeca-7,9-dien-6-one
SMILES
[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@]12[H]
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Cyclopropane and Derivatives
  • Halogen Derivatives
  • Alcohols and Polyols
  • Isoprenes
  • Cycloheptenes
  • Cyclohexenes and Derivatives
  • Ketones
Pharmacology
Indication For the palliative treatment of patients with advanced prostatic carcinoma.
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).
Mechanism 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.
Absorption Completely absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
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.
Route of elimination It is excreted approximately 60% in the bile and 33% through the kidneys.
Half life Elimination Following oral or intramuscular administration, the plasma half-life is 38 and 96 hours, respectively.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Liquid Intramuscular
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 6.65e-03 g/l ALOGPS
logP 3.37 ALOGPS
logP 3.2 ChemAxon
logS -4.8 ALOGPS
pKa (strongest acidic) 12.7 ChemAxon
pKa (strongest basic) -3.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 54.37 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 102.66 ChemAxon
polarizability 40.67 ChemAxon
References
Synthesis Reference Not Available
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
External Links
Resource Link
PubChem Compound 5284537 Link_out
PubChem Substance 46506931 Link_out
ChemSpider 4447594 Link_out
ChEBI 50742 Link_out
ChEMBL 50742 Link_out
Therapeutic Targets Database DAP000906 Link_out
PharmGKB PA10049 Link_out
Drug Product Database 704423 Link_out
Wikipedia http://en.wikipedia.org/wiki/Cyproterone Link_out
ATC Codes
  • G03HA01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take after a meal.
Targets

1. Androgen receptor

Pharmacological action: yes
Actions: antagonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3

Organism class: human
UniProt ID: P10275 Link_out
Gene: AR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Agoulnik IU, Weigel NL: Coactivator selective regulation of androgen receptor activity. Steroids. 2009 Aug;74(8):669-74. Epub 2009 Mar 9. Pubmed
  4. Cabeza M, Flores M, Bratoeff E, de la Pena A, Mendez E, Ceballos G: Intracellular Ca2+ stimulates the binding to androgen receptors in platelets. Steroids. 2004 Oct-Nov;69(11-12):767-72. Pubmed
  5. Sonneveld E, Jansen HJ, Riteco JA, Brouwer A, van der Burg B: Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays. Toxicol Sci. 2005 Jan;83(1):136-48. Epub 2004 Oct 13. Pubmed
Enzymes

1. Cytochrome P450 19A1

Actions: inhibitor

Catalyzes the formation of aromatic C18 estrogens from C19 androgens

UniProt ID: P11511 Link_out
Gene: CYP19A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on September 26, 2007 09:23 / Updated on February 08, 2013 16:23