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    Cyproterone Acetate
    Cyproterone Acetate

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1768
    CAS #: 427-51-0Purity ≥98%

    Description: Cyproterone acetate (Cyprone, Androcur, Cyprostat,Cyprohexal, Ciproterona, Cyproteron, Procur, Cyproteronum, Neoproxil, Siterone), an analog of 17-hydroxyprogesterone, is an androgen receptor (AR) antagonist with potential antitumor activity. It inhibits AR with an IC50 of 7.1 nM. Cyproterone acetate works by blocking androgen receptors which prevents androgens from binding to them and suppresses luteinizing hormone, which in turn reduces testosterone levels. It is primarily used to treat prostate cancer, benign prostatic hyperplasia, priapism, hypersexuality and other conditions. 

    References: Toxicol Sci. 2005 Jan;83(1):136-48; Mol Cell Endocrinol. 2010 Oct 26;328(1-2):16-21.

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    Molecular Weight (MW)416.94
    FormulaC24H29ClO4
    CAS No.427-51-0
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 83 mg/mL (199.1 mM)
    Water: <1 mg/mL
    Ethanol: 10 mg/mL (24.0 mM)
    Solubility (In vivo)1% DMSO+30% polyethylene glycol+1% Tween 80: 20 mg/mL 
    Other info

    Synonyms: Cyprone, Cyprohexal, Ciproterona, Cyproteronum, Androcur, Cyprostat,Cyproteron, Procur, Neoproxil, Siterone.

    Chemical Name: (2aR,3aS,3bS,3cS,5aS,6R,8aS,8bR)-6-acetyl-10-chloro-3b,5a-dimethyl-2-oxo-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-6-yl acetate

    InChi Key: UWFYSQMTEOIJJG-FDTZYFLXSA-N

    InChi Code: InChI=1S/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-/m0/s1

    SMILES Code: CC(O[[email protected]]1(C(C)=O)CC[[email protected]]2([H])[[email protected]]1(C)CC[[email protected]]3([H])[[email protected]@]4(C)[[email protected]](C5)([H])[[email protected]]5([H])C(C=C4C(Cl)=C[[email protected]@]23[H])=O)=O


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    In Vitro

    In vitro activity: Cyproterone acetate clearly shows antagonistic properties, while being a partial agonist also, showing agonism for the AR, with EC50 of 4.0 μM, at relatively high concentrations. In the presence of 10 nM Testosterone, low concentrations of Cyproterone acetate inhibits T-stimulated transcription of 3XHRE-LUC, but at higher concentrations, transcription is stimulated.

    In VivoLH levels in Cyproterone acetate-treated rats do not dip below pretreatment levels, although they does not increase as much in the rats treated with 3.2 mg Cyproterone acetate/kg/day as in those which received 0.2 mg Cyproterone acetate/kg/day. Cyproterone acetate exhibits direct negative effect on reproductive organs weight and significant reducing effect on sperm count and Ca2+ contents. SOD and GST activities significantly decrease in addition to significant increase in NO, MDA contents reflecting the oxidative status of testis in Cyproterone acetate treated rats. Cyproterone acetate treatment plus artificial long days in autumn has a negative effect on sperm motility and sperm morphology. Androgen receptor occupation by Cyproterone acetate preferentially reduces the levels of spermatidal protamine in testis and spermatozoa involved in nuclear chromatin condensation.  
    Animal modelCastrate male SD rat 
    Formulation & DosageDissolved in ethanol; 0.2 mg /kg/day; s.c administration
    References

    Toxicol Sci. 2005 Jan;83(1):136-48; Mol Cell Endocrinol. 2010 Oct 26;328(1-2):16-21.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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