Cyproterone Acetate

Alias: Cyprone, Cyprohexal, Ciproterona, Cyproteronum,Androcur, Cyprostat,Cyproteron, Procur, Neoproxil, Siterone.
Cat No.:V1768 Purity: ≥98%
Cyproterone acetate (Cyprone, Androcur, Cyprostat,Cyprohexal, Ciproterona, Cyproteron, Procur,Cyproteronum, Neoproxil, Siterone), an analog of17-hydroxyprogesterone, is an androgen receptor (AR) antagonist with potential antitumor activity.
Cyproterone Acetate Chemical Structure CAS No.: 427-51-0
Product category: Androgen Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Cyproterone Acetate:

  • Cyproterone acetate-d3
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product 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.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
At moderately high doses, cyproterone acetate, a partial agonist, exhibits agonism for the AR with an EC50 of 4.0 μM[1]. By upregulating death receptor 5, cyproterone acetate increases TRAIL-induced androgen-independent prostate cancer cell apoptosis[3]. Pretreatment with cyproterone acetate (0, 1, 10, or 50 μM) for 24 hours, followed by another 24 hours of cadmium exposure, clearly reduced the rat liver epithelial cell line's sensitivity to cadmium[4].
ln Vivo
The zona fasciculata and zona retjculans of the adrenal cortex of adult male C57 BL/6J mice injected with 0.08 mg/g of cyproterone acetate had an increase in cellular lipid content[5].
Animal Protocol
Dissolved in ethanol; 0.2 mg /kg/day; s.c administration
Castrate male SD rat
References
[1]. Sonneveld, E., et al., Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays. Toxicol Sci, 2005. 83(1): p. 136-48.
[2]. Torri V,. Cyproterone acetate in the therapy of prostate carcinoma. Arch Ital Urol Androl. 2005;77(3):157-163.
[3]. Chen L, et al. Cyproterone acetate enhances TRAIL-induced androgen-independent prostate cancer cell apoptosis via up-regulation of death receptor 5. BMC Cancer. 2017;17(1):179. Published 2017 Mar 7.
[4]. Takiguchi M, et al. Cyproterone acetate induces a cellular tolerance to cadmium in rat liver epithelial cells involving reduced cadmium accumulation. Toxicology. 2001;165(1):13-25.
[5]. Migally N. Effect of cyproterone acetate on the structure of the adrenal cortex. Arch Androl. 1979;2(2):109-115.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C24H29CLO4
Molecular Weight
416.94
CAS #
427-51-0
Related CAS #
Cyproterone acetate-d3;2376035-90-2
SMILES
CC(O[C@]1(C(C)=O)CC[C@]2([H])[C@]1(C)CC[C@]3([H])[C@@]4(C)[C@](C5)([H])[C@]5([H])C(C=C4C(Cl)=C[C@@]23[H])=O)=O
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
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
Synonyms
Cyprone, Cyprohexal, Ciproterona, Cyproteronum,Androcur, Cyprostat,Cyproteron, Procur, Neoproxil, Siterone.
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
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 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3984 mL 11.9921 mL 23.9843 mL
5 mM 0.4797 mL 2.3984 mL 4.7969 mL
10 mM 0.2398 mL 1.1992 mL 2.3984 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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