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E1001

Sigma-Aldrich

Ethisterone

≥99% (HPLC)

Synonym(s):

17α-Ethynyltestosterone, 17β-Hydroxy-4,17α-pregnen-20-yn-3-one, 4,17α-Pregnen-17β-ol-20-yn-3-one

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About This Item

Empirical Formula (Hill Notation):
C21H28O2
CAS Number:
434-03-7
Molecular Weight:
312.45
Beilstein:
1889895
EC Number:
207-096-5
MDL number:
MFCD00003656
UNSPSC Code:
12352200
PubChem Substance ID:
24894377
NACRES:
NA.77

biological source

synthetic (organic)

sterility

non-sterile

Assay

≥99% (HPLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

technique(s)

cell culture | mammalian: suitable

mp

263-269 °C (lit.)

solubility

chloroform: methanol (1:1): 20 mg/mL, clear to slightly hazy, colorless to light yellow

originator

Novartis

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@@]4(C)[C@H]3CC[C@@]4(O)C#C

InChI

1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI key

CHNXZKVNWQUJIB-CEGNMAFCSA-N

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General description

Ethisterone is a progestogen. It is a danazol derivative.

Application

Ethisterone has been used as a component in Dulbecco′s modified eagle medium (DMEM) to culture the transfected COS-7 cell for transient transfection assay and gene transfection assay.

Biochem/physiol Actions

Ethisterone acts as a progestational agent. It is consumed by pregnant mothers to prevent miscarriage.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H360FD,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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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Ambiguous Genitalia in the Newborn
Avery's Diseases of the Newborn, 1286-1306 (2012)
Evolutionary History and Functional Characterization of Androgen Receptor Genes in Jawed Vertebrates
Ogino Y, et al.
Endocrinology, 150(12), 5415-5427 (2009)
Junsu Kang et al.
Developmental cell, 27(1), 19-31 (2013-10-19)
Precise spatiotemporal regulation of signaling activators and inhibitors can help limit developmental crosstalk between neighboring tissues during morphogenesis, homeostasis, and regeneration. Here, we find that the secreted Wnt inhibitor Dkk1b is abundantly produced by dense regions of androgen-regulated epidermal tubercles
Cloning and expression analysis of androgen receptor gene in chicken embryogenesis
Katoh H, et al.
Febs Letters, 580(6), 1607-1615 (2006)
M Iqbal Choudhary et al.
Steroids, 70(12), 798-802 (2005-08-02)
The microbial transformation of the 17alpha-ethynyl-17beta-hydroxyandrost-4-en-3-one (1) (ethisterone) and 17alpha-ethyl-17beta-hydroxyandrost-4-en-3-one (2) by the fungi Cephalosporium aphidicola and Cunninghamella elegans were investigated. Incubation of compound 1 with C. aphidicola afforded oxidized derivative, 17alpha-ethynyl-17beta-hydroxyandrosta-1,4-dien-3-one (3), while with C. elegans afforded a new
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