Ethisterone Chemical Properties

Melting point:

263-269 °C (lit.)

Boiling point:

392.36°C (rough estimate)

alpha 

D23 +23.8° (dioxane); D25 -32.0° (pyridine)

Density 

1.0697 (rough estimate)

refractive index 

33 ° (C=1, Pyridine)

storage temp. 

room temp

solubility 

Soluble to 0.05 mg/mL (0.16 mM) in DMSO

pka

13.10±0.60(Predicted)

form 

Solid

color 

Light yellow to yellow

biological source

synthetic (organic)

Water Solubility 

soluble in chloroform, DMSO (0.05 mg/ml), acetone (slightly ), ethanol (<1 mg/ml at 25°C), and water (<1 mg/ml at 25°C).

Merck 

14,3741

BRN 

1889895

InChIKey

CHNXZKVNWQUJIB-CEGNMAFCSA-N

CAS DataBase Reference

434-03-7

NIST Chemistry Reference

Ethisterone(434-03-7)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

40-48-61

Safety Statements 

22-24/25-45-53

RIDADR 

UN 2811

WGK Germany 

3

RTECS 

TU5570250

HS Code 

29372390

MSDS

• Language:English Provider:Ethisterone
• Language:English Provider:SigmaAldrich

Ethisterone Usage And Synthesis

Description

Ethisterone is an orally bioavailable synthetic progestin and a derivative of testosterone (Item Nos. ISO60154 | 15645) that binds to progesterone and androgen receptors (EC₅₀s = 23 and 23.1 nM, respectively, in yeast). Ethisterone (1 μM) downregulates progesterone receptors in MCF-7 cells.

Chemical Properties

Off-White Powder

Originator

Lutocyclin,Ciba

Uses

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.

Uses

Synthetic progestogen; metabolite of Danazol; intermediate in the synthesis of Spironolactone

Definition

ChEBI: A 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol.

Manufacturing Process

0.5 part of δ5:6-17-ethinyl-androstendiol-(3:17) is dissolved in 10 parts of dry acetone, the solution is mixed with a solution of 1 part of tertiary aluminum butylate in 40 parts of absolute toluene and the whole is heated to boiling in a reflux apparatus for 21 hours. After the reaction mixture has cooled it is diluted with 100 parts of ether, the solution is washed with dilute mineral acid and with water, dried and the solvent is evaporated. In this manner there is obtained δ5:6-17-ethinyl-androstene-3-one-17-ol (ethisterone); MP: 270°- 272°C; it may be recrystallized from ethyl acetate.

Therapeutic Function

Progestin

General Description

Ethisterone is a?progestogen. It is a danazol derivative.

Biochem/physiol Actions

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

References

[1] L. MCROBB . Structure–activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay[J]. Journal of Steroid Biochemistry and Molecular Biology, 2008, 110 1: Pages 39-47. DOI: 10.1016/j.jsbmb.2007.10.008
[2] J.M. GLEDHILL . Progesterone receptor induction by danazol in cultured cancer cells and the rat uterus[J]. Journal of Steroid Biochemistry and Molecular Biology, 1992, 43 4: Pages 289-296. DOI: 10.1016/0960-0760(92)90163-d

Ethisterone(434-03-7)Related Product Information

• Testosterone
• 4'-Hydroxyacetophenone
• Zearalenone
• Quinocetone
• Androstenedione
• CHLOROPHOSPHONAZO III
• 2'-Hydroxyacetophenone
• Clethodim
• Gestrinone
• Norgestrel
• 6-Methyl-5-hepten-2-one
• 19-NOR-4-ETHISTERONE
• DIMETHISTERONE
• Progesterone
• Acetylene
• Oracon
• 2-hydroxy methylene ethisterone
• 2-(hydroxymethyl)ethisterone