Skip to Content
Merck
All Photos(2)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C24H29ClO4
CAS Number:
427-51-0
Molecular Weight:
416.94
EC Number:
207-048-3
MDL number:
MFCD00864671
UNSPSC Code:
41116107
PubChem Substance ID:
24278309
NACRES:
NA.77

Quality Level

100

Assay

≥98%

form

powder

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)

Looking for similar products? Visit Product Comparison Guide

Application

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

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H312 + H332,H351

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Cara L Benjamin et al.
The Journal of steroid biochemistry and molecular biology, 91(3), 111-119 (2004-07-28)
Skeletal muscle has long been thought to be a target tissue for androgens, eliciting their effect through the androgen receptor. In order to better understand androgen receptor action, a series of mutated androgen receptors were developed and their degree of
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)
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
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
View All Related Papers

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service