3836-23-5 Usage
Description
17alpha-Ethynyl-19-nortestosterone 17-heptanoate, also known as norethisterone enanthate, is a synthetic steroid hormone derived from testosterone. It is characterized by its chemical structure, which includes an ethynyl group at the 17alpha position and a heptanoate group at the 17 position. 17alpha-Ethynyl-19-nortestosterone 17-heptanoate is known for its chemico-chemical interactions and potential biological functions.
Uses
Used in Pharmaceutical Industry:
17alpha-Ethynyl-19-nortestosterone 17-heptanoate is used as a pharmaceutical compound for its antigonadotropic effects. It serves as a hormonal contraceptive, helping to prevent pregnancy by suppressing ovulation and altering the cervical mucus and the uterine lining.
Used in Research and Development:
In the field of research and development, 17alpha-Ethynyl-19-nortestosterone 17-heptanoate is used as a study compound to understand chemico-chemical interactions. This knowledge aids in predicting the biological functions and potential applications of similar compounds in various fields, including medicine and pharmaceuticals.
Brand Names:
Some of the brand names under which 17alpha-Ethynyl-19-nortestosterone 17-heptanoate is marketed include Binovum, Brevicon, Brevinor, Conceplan, Doryxas, Gesta plan, LG 335, Menonorm, Miconor, Neocon, Nor 50, Norimin, Noristerat, Norlutate acetate, Nor-Q-D, Norquentiel, Norquest FE, Novulon, Nur-Isterate, Orlestrin, Ortho-Novum, Ovcon-50, Ovismen, Ovysmen, and Tri-Norinyl.
Originator
Norigest,Schering
Manufacturing Process
1 g 17-ethinyl-19-nor-testosteron was refluxed with 5 ml of enanthic acid anhydride on an oil bath at temperature 180°C 17 hours. Then the reaction mixture was distilled with water steam to the full disappearence of smell of enantic acid. After that it was washed with 2 N sodium hydroxide and finally with water to neutral, dried over sodium sulfate and evaporated to dryness. The oily residue was rubbed with some drops of methanol and stood at -8°C 24 hours to give the crystals of 3-endol diester; MP: 82°-84°C, 2 g of it was dissolved in 120 ml of methanol and heated with 1.2 ml concentrated hydrochloric acid. The partly saponified product was distilled with water steam
to full disappearence of smell of enantic acid. The residue was mixed with ether, washed with 2 N sulfuric acid, 2 N sodium hydroxide, finally with water to neutral dried over sodium sulfate and evaporated to dryness. The residue was stirred with pentane and cooled for crystallization. Pure enanthate was crystallized after repeated solution in pentane. 17-α-Ethinyl-19nortestosterone enanthate had MP: 68°-71°C.
Therapeutic Function
Progestin
World Health Organization (WHO)
Norethisterone enantate was introduced in 1978 for use as a longacting
injectable contraceptive. Risk-benefit judgements differ significantly from
country to country, having regard to differing national circumstances.
Norethisterone enantate is, however, widely available and is included as a
complementary drug in the WHO Model List of Essential Drugs.
(Reference: (WHODI) WHO Drug Information, 2(1), , 1988)
Safety Profile
An experimental teratogen.Questionable carcinogen with experimental tumorigenicdata. Human systemic effects by intravenous route:increased intraocular pressure. Human reproductiveeffects by intramuscular route: menstrual cycle changes ordisorders, ch
Check Digit Verification of cas no
The CAS Registry Mumber 3836-23-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,8,3 and 6 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3836-23:
(6*3)+(5*8)+(4*3)+(3*6)+(2*2)+(1*3)=95
95 % 10 = 5
So 3836-23-5 is a valid CAS Registry Number.
InChI:InChI=1/C27H38O3/c1-4-6-7-8-9-25(29)30-27(5-2)17-15-24-23-12-10-19-18-20(28)11-13-21(19)22(23)14-16-26(24,27)3/h2,18,21-24H,4,6-17H2,1,3H3
3836-23-5Relevant articles and documents
An Efficient Method for Preparation of Norethisterone Esters
Lal, Kasturi,Kole, P. L.,Ray, Suprabhat
, p. 682 (2007/10/02)
Condensation of norethisterone with fatty acids in the presence of dicyclohexylcarbodiimide and 4-N,N-dimethylaminopyridine gives corresponding esters in excellent yields.This has implication in large scale preparation.
