Chemistry:Quingestanol acetate
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| Trade names | Demovis, Pilomin, others |
| Other names | 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 |
| Routes of administration | By mouth |
| Drug class | Progestogen; Progestin; Progestogen ester |
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| Formula | C27H36O3 |
| Molar mass | 408.582 g·mol−1 |
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Quingestanol acetate, sold under the brand names Demovis and Pilomin among others, is a progestin medication which was used in birth control pills but is no longer marketed.[1] It is taken by mouth.[2][3][4]
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.[2][3][4] It has weak androgenic and estrogenic activity and no other important hormonal activity.[2][3][4] The medication is a prodrug of norethisterone in the body, with quingestanol and norethisterone acetate occurring as intermediates.[5][6]
Quingestanol acetate was patented in 1963 and was introduced for medical use in 1972.[7][8] It was marketed in Italy.[8]
Medical uses
Quingestanol acetate was used as an oral, once-a-month, or postcoital hormonal contraceptive.[2][3][4]
Side effects
Pharmacology
Quingestanol acetate is a progestogen, and also has weak androgenic and estrogenic activity.[2][3][4] It is a prodrug of norethisterone, with both quingestanol and norethisterone acetate serving as intermediates in the transformation.[5][6] 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.[2]
Chemistry
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.[1] 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.[1] Quingestanol acetate is the C17β acetate ester of quingestanol (norethisterone 3-cyclopentyl enol ether).[1]
History
Quingestanol acetate was patented in 1963[7] and marketed in Italy in 1972.[8][9]
Society and culture
Generic names
Quingestanol acetate is the generic name of the drug and its INN and USAN.[1]
Brand names
Quingestanol acetate was marketed under the brand names Demovis, Pilomin, Riglovis, and Unovis.[1][7]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1058–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1058.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Biological profile of quingestanol acetate". Proceedings of the Society for Experimental Biology and Medicine 131 (3): 781–9. July 1969. doi:10.3181/00379727-131-33977. PMID 5815452.
- ↑ 3.0 3.1 3.2 3.3 3.4 "Further experience with quingestanol acetate as a postcoital oral contraceptive". Contraception 9 (3): 221–5. March 1974. doi:10.1016/0010-7824(74)90013-4. PMID 4613534.
- ↑ 4.0 4.1 4.2 4.3 4.4 "Biochemical studies with once-a-month contraceptive pill containing quinestrol-quingestanol acetate". Contraception 11 (6): 681–8. June 1975. doi:10.1016/0010-7824(75)90065-7. PMID 1137940.
- ↑ 5.0 5.1 "The design and use of sex-steroid antagonists". J. Steroid Biochem. 25 (5B): 811–33. 1986. doi:10.1016/0022-4731(86)90313-4. PMID 3543501. "Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).".
- ↑ 6.0 6.1 "Quingestanol acetate metabolism in women". Pharmacology 11 (5): 287–303. 1974. doi:10.1159/000136501. PMID 4853997.
- ↑ 7.0 7.1 7.2 Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7. https://books.google.com/books?id=_i-s4biQs7MC&pg=PA73.
- ↑ 8.0 8.1 8.2 Population Reports: Oral contraceptives. Department of Medical and Public Affairs, George Washington Univ. Medical Center.. 1975. p. A-64. https://books.google.com/books?id=lqVLAQAAIAAJ.
- ↑ Janne S. Kowalski (1 August 1988). Drug companies & products world guide. Sittig & Noyes. p. 388. ISBN 9780800242398. https://books.google.com/books?id=6i5tAAAAMAAJ.
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