Oxendolone Chemical Properties

Melting point:

152-153℃

alpha 

D +41° (c = 1.0 in ethanol)

Boiling point:

383.47°C (rough estimate)

Density 

1.0434 (rough estimate)

refractive index 

1.4980 (estimate)

pka

15.08±0.60(Predicted)

Safety Information

Toxicity

LD50 in rats, mice (g/kg): >10 orally; 5-10 i.m. and i.p. (Hiraga, 1971)

Oxendolone Usage And Synthesis

Description

Oxendolone can be used as an anti-androgen drug and has an anti-androgen effect. Competitive antagonism occurs directly with male hormones in the prostate, inhibiting the weight of the prostate and seminal vesicles. The specificity of its anti-androgen effect is high, and it directly competes with androgens in the prostate and hardly shows other hormonal effects.

?Acute toxicity

LD50 in rats and mice (g/kg): >10 orally; 5-10 intramuscular injection and intraperitoneal injection

Chemical Properties

Crystallized from diethyl ether, melting point 152-153°C. [α]D +41° (C = 1.0, ethanol). UV absorption maximum (ethanol): 240 nm (ε 15800). Stable to heat, moisture, and light. Converts to 16α- and 17α-isomers under sunlight. Acute toxicity LD50 in rats and mice (g/kg): >10 for oral administration; 5-10 for intramuscular and intraperitoneal injections.

Originator

Prostetin,Takeda, Japan ,1981

Uses

Oxendolone is used as an anti-androgen (benign prostatic hypertrophy).

Definition

ChEBI: Oxendolone is an organic molecular entity.

Manufacturing Process

To a solution of 3.0 g of 16β-ethylestra-4-ene-3,17-dione dissolved in 150 ml of dioxane, are added 15 g of ethyl orthoformate and 0.1 g of ptoluenesulfonic acid, followed by stirring for 2 hours at room temperature. The reaction solution is poured into 300 ml of a 5% aqueous solution of sodium hydrogen carbonate and the resultant mixture is extracted with ether. The ether layer is washed with water and dried, followed by evaporation of the solvent to give crude crystals of 3-ethoxy-16β-ethylestra-3,5-diene-17-one. The crystals are recrystallized from ether to give 3.0 g of the compound melting at 114°C to 115°C
To a solution of 3.0 g of the enol-ether compound obtained above in 50 ml of methanol, is added 1.5 g of sodium borohydride. After standing for 1.5 hours at room temperature, the reaction solution is poured into 300 ml of water. The resulting precipitates are collected by filtration and recrystallized from ether to give 2.8 g of 3-ethoxy-16β-ethylestra-3,5-dien-17β-ol melting at 131°C to 133°C.
To a solution of 2.5 g of 3-ethoxy-16β-ethylestra-3,5-diene-17β-ol dissolved in 50 ml of methanol is added 1.2 ml of concentrated hydrochloric acid, followed by stirring for 10 minutes. The reaction solution is poured into 250 ml of water. The precipitated crystals are collected by filtration and recrystallized from ether to give 2.3 g of 16β-ethyl-17β-hydroxyestra-4-en-one melting at 152°C to 153°C.

Therapeutic Function

Antiandrogen

Oxendolone(33765-68-3)Related Product Information

• ESTR-4-EN-17-ONE
• Estr-4-en-3-one, 17-(1-oxododecyl)oxy-, (17.beta.)-,(17b)-17-[(1-oxododecyl)oxy]-estr-4-en-3-one
• Oxendolone
• 17-Hydroxy-estr-4-en-3-one,Estr-4-en-3-one, 17-hydroxy-, (17b)- (9CI),Estr-4-en-3-one, 17b-hydroxy- (8CI)
• 17-HYDROXY-7,17-DIMETHYL-ESTR-4-EN-3-ONE
• 17β-[(1-Oxoundecyl)oxy]estr-4-en-3-one
• Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-
• Estr-9-en-3-one, 11-[4-(dimethylamino)phenyl]-5,17-dihydroxy-17-(1-propynyl)-, cyclic 1,2-ethanediyl acetal, (5a,11b,17b)-
• Nandrolone Decanoate
• Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-, acetate
• 17β-[(Tricyclo[3.3.1.13,7]dec-1-ylcarbonyl)oxy]estr-4-en-3-one
• 17β-[[(Sodiooxy)sulfonyl]oxy]estr-4-en-3-one,Estr-4-en-3-one, 17-(sulfooxy)-, sodium salt, (17beta)-
• Estr-4-en-3-one, 17alpha-ethyl-17-hydroxy-
• Nandrolone phenylpropionate
• 17beta-hydroxyestr-4-en-3-one 17-(3-cyclohexylpropionate)
• 17beta-hydroxyestr-4-en-3-one 17-[3-(2-furyl)propionate]
• 17β-[(1-Oxohexyl)oxy]estr-4-en-3-one
• 17β-[(1-Oxopentyl)oxy]estr-4-en-3-one