Description
Ethynodiol diacetate is a synthetic progestogen. It prevents the development of osteoporosis in ovariectomized rats when administered at a dose of 9 μg/animal per day. Ethynodiol diacetate inhibits copulatory ovulation in rabbits. Formulations containing ethynodiol diacetate have been used as oral contraceptives.
Originator
Lutometrodiol,Searle,France,1965
Uses
Ethynodiol Diacetate is used as a hormonal contraceptive, birth control.
Definition
ChEBI: Ethynodiol diacetate is a steroid ester and a terminal acetylenic compound. It has a role as an estrogen receptor modulator, a contraceptive drug and a synthetic oral contraceptive. It is functionally related to an ethynodiol.
Manufacturing Process
A mixture of 30 parts of 17α-ethynyl-19-norandrost-4-ene-3β,17β-diol, 360
parts of dry pyridine, and 111 parts of acetic anhydride, under nitrogen, is
stirred and heated at the reflux temperature for about 5 hours. This reaction
mixture is cooled, then poured into approximately 3,500 parts of cold water
and the resulting aqueous mixture is stirred at room temperature for about
0.5 hour. The precipitate which forms is collected by filtration, then is washed
on the filter with water and dried in air. This solid material is extracted into
ether, and the ether solution is washed successively with 10% aqueous
Therapeutic Function
Progestin; Oral contraceptive ingredient
General Description
Ethynodiol diacetate, 19-norpregn-4-en-20-yne-3β,17α-diol diacetate, is a prodrug ofnorethindrone. A combination of hydrolysis of both estersand oxidation of the C3 alcohol to the ketone is necessary toprovide the fully active progestin.
Safety Profile
Suspected carcinogen.
Human reproductive effects by ingestion:
menstrual cycle changes. Experimental
reproductive effects. Mutation data
reported. A steroid. When heated to decomposition it emits acrid smoke and
irritating fumes.
References
[1] J M AITKEN J B A E Armstrong. Osteoporosis after oophorectomy in the mature female rat and the effect of oestrogen and-or progestogen replacement therapy in its prevention.[J]. Journal of Endocrinology, 1972, 55 1: 79-87. DOI:
10.1677/joe.0.0550079[2] M SUZUKI K T M Hiroi. Effects of ethynodiol diacetate (SC 11800) on the pregnancy and mating behavior in female rats.[J]. Tohoku Journal of Experimental Medicine, 1972, 107 4: 317-322. DOI:
10.1620/tjem.107.317
