DIENESTROL

Chemical properties

Colorless, needles or powder; odorless. Soluble in alcohol; practically insoluble in water; sensitive to light.

Originator

Synestrol,Schering,US,1947

The Uses of DIENESTROL

Dienestrol is a metabolite of Diethylstilbestrol, a non-steroidal synthetic estrogen derivative.

The Uses of DIENESTROL

Medicine (estrogenic hormone).

What are the applications of Application

Dienestrol is A non-steroidal estrogen structurally related to stilbestrol

Definition

ChEBI: An olefinic compound that is hexa-2,4-diene substituted by 4-hydroxyphenyl groups at positions 3 and 4 respectively.

Manufacturing Process

Preparation of γ,δ-Bis-(4-Hydroxylphenyl)-Hexane-γ,δ-Diol: A sodium amalgam is prepared containing 6 grams of sodium and 400 grams of mercury. The amalgam is covered with a solution of 20 grams of 4-hydroxypropiophenone in a mixture of 30 ml of 5 N sodium hydroxide solution and 220 ml of water and the mixture is heated to 28°-30°C and stirred gently. The reduction is accompanied by development of heat and the temperature of the solution rises to 34°-35°C, and then falls slowly. After 5 hours the alkaline solution is separated from the mercury and diluted with 3 or 4 times its volume of water, when, in order to form the benzoyl derivatives of the products, the solution is vigorously stirred, while it is being cooled, with 20 ml of benzoyl chloride, the solution being kept at a temperature of 15°-20°C. When the reaction is completed, the benzoyl derivatives are filtered off, washed with water and recrystallized from a mixture of benzene and alcohol, when a product with a melting point of 195°-215°C is obtained.
Preparation of Dienestrol: In order to obtain dienoestrol, 14.6 grams of dry 4,4'-dibenzoate are refluxed with a mixture of 40 ml of acetic anhydride and 40 ml acetylchloride by heating in an oil-bath at about 90°C for 6 hours after which the bath temperature is increased to 120°C and heating continued for a further 18 hours, after which time the evolution of hydrogen chloride practically ceases. The mixture is allowed to cool for several hours and the crystals which separate are filtered off and recrystallized from an alcoholbenzene mixture when the product melts at 210°-222°C. This product is converted into dienoestrol by adding 10.8 grams of it to 100 ml of 10% (w/v) alcoholic potassium hydroxide solution and then refluxing during 1 hour. After dilution with 200 ml of water and filtration from a small amount of insoluble material, dienoestrol is precipitated from the alkaline solution by treatment with carbon dioxide. It is filtered off, washed with water and recrystallized from dilute alcohol after which it melts at 233°-234°C according to US Patent 2,464,203.

brand name

Avc/dienestrol;Crinohermal fem;D.v.;Dienostrol cream;Dienstrogen;Dinol;Dufemine;Foragynol;Frein;Klianyi forte;Klianyl;Neo-oestrogenine;Ortho (cream);Ortho dienestrol cream.

Therapeutic Function

Estrogen

World Health Organization (WHO)

Dienestrol is a stilbene derivative. See WHO comment for diethylstilbestrol. Vaginal forms of dienestrol, which were introduced in 1947, are currently available in over 35 countries for the management of hypoestrogenic vaginal atrophy. (Reference: (WHODI) WHO Drug Information, 77.1, 16, 1977)

Safety Profile

Suspected human carcinogen. Human mutation data reported. Experimental reproductive effects. Used as a drug for the treatment of postmenopausal symptoms. When heated to decomposition it emits acrid smoke and irritating fumes.