C3412

Sigma-Aldrich

Cyproterone acetate

≥98%

Synonym(s):
6-Chloro-1β,2β-dihydro-17-hydroxy-3′H-cyclopropa(1,2)-pregna-1,4,6-triene-3,20-dione acetate
Empirical Formula (Hill Notation):
C24H29ClO4
CAS Number:
Molecular Weight:
416.94
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥98%

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]34C

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

InChI key

UWFYSQMTEOIJJG-FDTZYFLXSA-N

Gene Information

human ... AR(367), NR3C1(2908), PGR(5241)
mouse ... Nr3c1(14815)
rat ... Ar(24208)

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Application

Cyproterone acetate has been used to study its effects on insulin-like growth factor I secretion.

Packaging

250 mg in poly bottle

Biochem/physiol Actions

Cyproterone acetate is a synthetic steroid and an androgen antagonist. It is a potent inhibitor of leukocyte migration through endothethial cell monolayers. Cyproterone acetate acts as a liver tumor promoter in experimental animal model. Liver tumor promotion appears to be female gender-specific, as formation of an active metabolite that forms DNA adducts.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C3412.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

20/21/22-40

Safety Statement

22-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
M J Tucker et al.
Carcinogenesis, 17(7), 1473-1476 (1996-07-01)
The synthetic progestin cyproterone acetate (CPA) has been shown to be a hepatocarcinogen in the rat, but little is known of its effects in mice. A 52 week CPA study in the mouse strain C57Bl/10J has been reported not to...
Cody J Dey et al.
Hormones and behavior, 58(4), 599-605 (2010-07-10)
Proximate mediators of reproductive behaviors in vertebrates have a long history of study. In fishes, relatively few studies have focused on hormonal control of parental care, despite a comprehensive background on the general physiology of fishes, and the frequent occurrence...
R Hofbauer et al.
Fertility and sterility, 72(4), 652-656 (1999-10-16)
To investigate the influence of ethinyl estradiol and cyproterone acetate in oral contraceptives on leukocyte migration through endothelial cell monolayers. Experimental in vitro prospective study. An academic research laboratory. Endothelial cells were cultured on microporous membranes to produce monolayers. Polymorphonuclear...
Cyproterone, norethindrone, medroxyprogesterone and levonorgestrel are less potent local human growth hormone and insulin-like growth factor I secretion stimulators than progesterone in human breast cancer explants expressing the estrogen receptor
Milewicz T, et al.
Gynecological Endocrinology, 16(4), 319-329 (2002)
Lucía Cea-Soriano et al.
Cancer epidemiology, 36(2), 198-205 (2011-09-29)
The aetiology of meningiomas is largely unknown although hormones have been suggested to play a role. A cohort study was performed to evaluate hormone-related factors associated with meningioma. Patients (12-89 years) with a first diagnosis of meningioma (January 1996-June 2008)...
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Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.
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