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Cyproterone

July 24, 2017
Common Name

Cyproterone 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 Cyproterone, 1alpha,2 alpha,9 beta,10 alpha-isomerMeSH

Chemical Formlia

C22H27ClO3 Average Molecliar Weight

374.901 Monoisotopic Molecliar Weight

374.164872437 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 Name

cyproterone CAS Registry Number

2098-66-0 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 Key

DUSHUSLJJMDGTE-ZJPMUUANSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Steroids and steroid derivatives Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives Alternative Parents

  • 20-oxosteroids
  • Halogenated steroids
  • 3-oxosteroids
  • 17-hydroxysteroids
  • Cyclohexenones
  • Tertiary alcohols
  • Alpha-hydroxy ketones
  • Cyclic alcohols and derivatives
  • Vinyl chlorides
  • Chloroalkenes
  • Organochlorides
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxosteroid
  • 6-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Cyclohexenone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Ketone
  • Vinyl halide
  • Vinyl chloride
  • Haloalkene
  • Chloroalkene
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • 17alpha-hydroxy steroid (CHEBI:50742 )
  • 3-oxo Delta(4)-steroid (CHEBI:50742 )
  • 20-oxo steroid (CHEBI:50742 )
  • chlorinated steroid (CHEBI:50742 )

    • Ontology Status

    Expected 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 Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility6.65e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04839

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04839

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04839 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4447594 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cyproterone NuGOwiki Link

    HMDB15587 Metagene Link

    HMDB15587 METLIN ID

    Not Available PubChem Compound

    5284537 PDB ID

    Not Available ChEBI ID

    50742

    Product: Solifenacin (hydrochloride)

    References Synthesis Reference Not 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. [PubMed: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. [PubMed:17016423 ]
    3. Agoulnik IU, Weigel NL: Coactivator selective regulation of androgen receptor activity. Steroids. 2009 Aug;74(8):669-74. doi: 10.1016/j.steroids.2009.02.007. Epub 2009 Mar 9. [PubMed: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. [PubMed: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. [PubMed:15483189 ]

    PMID: 20208034

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