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2098-66-0 molecular structure
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(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one

ChemBase ID: 4383
Molecular Formular: C22H27ClO3
Molecular Mass: 374.90098
Monoisotopic Mass: 374.1648724
SMILES and InChIs

SMILES:
ClC1=C[C@@H]2[C@@H]([C@]3([C@@H]4[C@@H](C4)C(=O)C=C13)C)CC[C@]1([C@H]2CC[C@]1(O)C(=O)C)C
Canonical SMILES:
O=C1C=C2C(=C[C@@H]3[C@@H]([C@]2([C@@H]2[C@H]1C2)C)CC[C@]1([C@H]3CC[C@]1(O)C(=O)C)C)Cl
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
InChIKey:
DUSHUSLJJMDGTE-ZJPMUUANSA-N

Cite this record

CBID:4383 http://www.chembase.cn/molecule-4383.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
(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
IUPAC Traditional name
cyproterone
Brand Name
Androcur
Apo-cyproterone
Gen-Cyproterone
Novo-cyproterone
CyPat
Synonyms
Cyproterone acetate
(1β,2β)-6-Chloro-1,2-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
6-Chloro-6-dehydro-17α-hydroxy-1,2α-methyleneprogesterone
6-Chloro-17-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione
1,2α-Methylene-6-chloro-6-17α-hydroxyprogesterone
Cyproterone acetate
Cyproterone
CAS Number
2098-66-0
PubChem SID
160967815
46506931
PubChem CID
5284537
CHEBI ID
50742
ATC CODE
G03HA01
CHEMBL
142130
Chemspider ID
4447594
DrugBank ID
DB04839
KEGG ID
D07766
Unique Ingredient Identifier
E61Q31EK2F
Wikipedia Title
Cyproterone
Cyproterone_acetate

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
C989090 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.6991005  H Acceptors
H Donor LogD (pH = 5.5) 3.1977315 
LogD (pH = 7.4) 3.1977293  Log P 3.1977315 
Molar Refractivity 102.658 cm3 Polarizability 39.728195 Å3
Polar Surface Area 54.37 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.37  LOG S -4.75 
Solubility (Water) 6.65e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
208-210°C expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
oral, intramuscular expand Show data source
Bioavailability
100% expand Show data source
Excretion
60% bile, 33% renal expand Show data source
Half Life
about 40 hours expand Show data source
Metabolism
hepatic expand Show data source
Protein Bound
96% expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
X expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB04839 external link
Item Information
Drug Groups approved; investigational
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]
Indication For the palliative treatment of patients with advanced prostatic carcinoma.
Pharmacology 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).
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Completely absorbed following oral administration.
Half Life Elimination Following oral or intramuscular administration, the plasma half-life is 38 and 96 hours, respectively.
Elimination It is excreted approximately 60% in the bile and 33% through the kidneys.
References
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]
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]
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]
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]
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
Wikipedia
Toronto Research Chemicals - C989090 external link
An antiandrogen, suppresses Testosterone and its metabolites. Derivatives of Cyproterone are administered to patients suffering from hypersexuality and to help facilitate the sexual transformation of male-to-female transsexuals.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • 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
  • • 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
  • • 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
  • • 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
  • • Gracia, T., et al.: Toxicol. App. Pharmacol., 225, 142 (2007)
  • • Ahlin, G., et al.: J. Med. Chem., 51, 5932 (2007)
  • • Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2007)
  • • Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2007)
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