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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:30 UTC
HMDB IDHMDB15587
Secondary Accession NumbersNone
Metabolite Identification
Common NameCyproterone
DescriptionAn 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
Synonyms
ValueSource
6-Chlor-delta(6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteronChEBI
apo-CyproteroneChEBI
CiproteronaChEBI
CiproteroneChEBI
CyproteronumChEBI
novo-CyproteroneChEBI
6-Chlor-delta(6)-1,2-a-methylen-17-a-hydroxyprogesteronGenerator
6-Chlor-δ(6)-1,2-α-methylen-17-α-hydroxyprogesteronGenerator
6-Chlor-δ(6)-1,2-a-methylen-17-a-hydroxyprogesteronGenerator
Cyproterone acetateHMDB
Chemical FormulaC22H27ClO3
Average Molecular Weight374.901
Monoisotopic Molecular Weight374.164872437
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
Traditional Namecyproterone
CAS Registry Number2098-66-0
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]
InChI Identifier
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
InChI KeyInChIKey=DUSHUSLJJMDGTE-ZJPMUUANSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • 3-oxosteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Androgen Antagonists
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.65e-03 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0066 mg/mLALOGPS
logP3.37ALOGPS
logP3.2ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity102.66 m3·mol-1ChemAxon
Polarizability40.67 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04839
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04839
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04839
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447594
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyproterone
NuGOwiki LinkHMDB15587
Metagene LinkHMDB15587
METLIN IDNot Available
PubChem Compound5284537
PDB IDNot Available
ChEBI ID50742
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [4001026 ]
  2. 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. [4125095 ]
  3. 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. [6227191 ]
  4. 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. [6237971 ]
  5. 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. [12695529 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
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. [19934256 ]
General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9
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. [17139284 ]
  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. [17016423 ]
  3. Agoulnik IU, Weigel NL: Coactivator selective regulation of androgen receptor activity. Steroids. 2009 Aug;74(8):669-74. Epub 2009 Mar 9. [19463689 ]
  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. [15579329 ]
  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. [15483189 ]