297-76-7 Usage
Description
Ethynodiol diacetate, also known as 19-norpregn-4-en-20-yne-3β,17α-diol diacetate, is a synthetic progestogen and a prodrug of norethindrone. It is a hormone that plays a crucial role in the regulation of the menstrual cycle and pregnancy. Ethynodiol diacetate is transformed into the fully active progestin through a combination of hydrolysis of both esters and oxidation of the C3 alcohol to the ketone. This synthetic hormone has various applications in the medical field, particularly in contraception and anticonvulsant treatments.
Uses
Used in Contraceptive Applications:
Ethynodiol diacetate is used as a hormonal contraceptive in the form of birth control. It works by inhibiting ovulation, altering the cervical mucus to prevent sperm penetration, and changing the lining of the uterus to reduce the chances of implantation. Formulations containing ethynodiol diacetate have been widely used as oral contraceptives, providing an effective method for family planning and preventing unintended pregnancies.
Used in Anticonvulsant Applications:
Ethynodiol diacetate is also utilized as an anticonvulsant, helping to control and prevent seizures in patients with epilepsy or other seizure disorders. The exact mechanism of action is not fully understood, but it is believed to work by stabilizing the electrical activity in the brain, reducing the likelihood of seizures.
Used in Osteoporosis Prevention:
Ethynodiol diacetate has been shown to prevent the development of osteoporosis in ovariectomized rats when administered at a dose of 9 μg/animal per day. This suggests that it may have potential applications in the prevention and treatment of osteoporosis in humans, particularly in postmenopausal women who are at a higher risk of developing this bone-weakening condition.
Originator
Lutometrodiol,Searle,France,1965
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 297-76-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 7 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 297-76:
(5*2)+(4*9)+(3*7)+(2*7)+(1*6)=87
87 % 10 = 7
So 297-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C24H32O4/c1-5-16-13-22-21-8-6-17-12-18(27-14(2)25)7-9-19(17)20(21)10-11-24(22,4)23(16)28-15(3)26/h1,12,16,18-23H,6-11,13H2,2-4H3/t16-,18+,19?,20?,21?,22?,23+,24+/m1/s1
