|Trade names||Demovis, Pilomin, others|
|Synonyms||W-4540; Norethisterone acetate 3-cyclopentyl enol ether; 17α-Ethynyl-19-nortestosterone acetate 3-cyclopentyl enol ether; ENTACP; (17β)-3-(Cyclopentyloxy)-17-ethynylestra-3,5-dien-17-yl acetate|
|Drug class||Progestin; Progestogen; Progestogen ester|
|Chemical and physical data|
|Molar mass||408.573 g/mol|
|3D model (JSmol)|
Quingestanol acetate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak androgenic and estrogenic activity and no other important hormonal activity. The medication is a prodrug of norethisterone in the body, with quingestanol and norethisterone acetate occurring as intermediates.
Quingestanol acetate is a progestogen, and also has weak androgenic and estrogenic activity. It is a prodrug of norethisterone, with both quingestanol and norethisterone acetate serving as intermediates in the transformation. Unlike penmesterol (methyltestosterone 3-cyclopentyl enol ether) and quinestrol (ethinylestradiol 3-cyclopentyl ether), quingestanol acetate is not stored in fat and does not have a prolonged duration of action.
Quingestanol acetate, also known as norethisterone 17β-acetate 3-cyclopentyl enol ether or as 17α-ethynyl-19-nortestosterone 17β-acetate 3-cyclopentyl enol ether (ENTACP), as well as 3-(cyclopentyloxy)-17α-ethynylestra-3,5-dien-17β-yl acetate, is a synthetic estrane steroid and a derivative of testosterone. It is specifically a derivative of 19-nortestosterone and 17α-ethynyltestosterone, or of norethisterone (17α-ethynyl-19-nortestosterone), in which a cyclopentyl enol ether group has been attached at the C3 position and an acetate ester has been attached at the C17β position. Quingestanol acetate is the C17β acetate ester of quingestanol (norethisterone 3-cyclopentyl enol ether).
Quingestanol acetate was patented in 1963 and marketed in Italy in 1972.
Society and culture
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- Giannina T, Steinetz BG, Rassaert CL, McDougall EA, Meli A (July 1969). "Biological profile of quingestanol acetate". Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 131 (3): 781–9. doi:10.3181/00379727-131-33977. PMID 5815452.
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Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).
- Di Carlo FJ, Loo JC, Aceto T, Zuleski FR, Barr WH (1974). "Quingestanol acetate metabolism in women". Pharmacology. 11 (5): 287–303. doi:10.1159/000136501. PMID 4853997.
- Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7.
- Population Reports: Oral contraceptives. Department of Medical and Public Affairs, George Washington Univ. Medical Center. 1975. p. A-64.
- Janne S. Kowalski (1 August 1988). Drug companies & products world guide. Sittig & Noyes. p. 388.