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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

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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

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)

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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’.

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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
Marta Díaz et al.
The Journal of clinical endocrinology and metabolism, 97(10), 3630-3638 (2012-07-14)
The aim was to compare the effects of a traditional therapy (an oral estroprogestagen) to those of a novel treatment (a low-dose combination of generics) in adolescent girls with androgen excess. In an open-label trial over 1 yr, 34 adolescents
Lourdes Ibáñez et al.
The Journal of clinical endocrinology and metabolism, 96(11), 3361-3366 (2011-08-26)
The aim was to perform a first comparison between the effects of a classic therapy and those of a novel treatment for androgen excess in adolescent girls. We conducted a randomized, open-labeled trial at a university hospital. Thirty-four adolescents with
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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