Quingestanol acetate explained

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.

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 was patented in 1963 and was introduced for medical use in 1972. It was marketed in Italy.

Medical uses

Quingestanol acetate was used as an oral, once-a-month, or postcoital hormonal contraceptive.

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.

Chemistry

See also: List of progestogens, Progestogen ester and List of progestogen esters.

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).

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 and .

Brand names

Quingestanol acetate was marketed under the brand names Demovis, Pilomin, Riglovis, and Unovis.

Notes and References

1. Book: J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 1058–.
2. Giannina T, Steinetz BG, Rassaert CL, McDougall EA, Meli A . Biological profile of quingestanol acetate . Proceedings of the Society for Experimental Biology and Medicine. 131 . 3 . 781–9 . July 1969 . 5815452 . 10.3181/00379727-131-33977. 12433167 .
3. Mischler TW, Rubio B, Larranaga A, Guiloff E, Moggia AV . Further experience with quingestanol acetate as a postcoital oral contraceptive . Contraception . 9 . 3 . 221–5 . March 1974 . 4613534 . 10.1016/0010-7824(74)90013-4.
4. Donde UM, Virkar KD . Biochemical studies with once-a-month contraceptive pill containing quinestrol-quingestanol acetate . Contraception . 11 . 6 . 681–8 . June 1975 . 1137940 . 10.1016/0010-7824(75)90065-7.
5. Raynaud JP, Ojasoo T . The design and use of sex-steroid antagonists . J. Steroid Biochem. . 25 . 5B . 811–33 . 1986 . 3543501 . 10.1016/0022-4731(86)90313-4. Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol)..
6. Di Carlo FJ, Loo JC, Aceto T, Zuleski FR, Barr WH . Quingestanol acetate metabolism in women . Pharmacology . 11 . 5 . 287–303 . 1974 . 4853997 . 10.1159/000136501.
7. Book: Lara Marks. Sexual Chemistry: A History of the Contraceptive Pill. 2010. Yale University Press. 978-0-300-16791-7. 73–.
8. Book: Population Reports: Oral contraceptives. 1975. Department of Medical and Public Affairs, George Washington Univ. Medical Center.. A-64.
9. Book: Janne S. Kowalski. Drug companies & products world guide. 1 August 1988. Sittig & Noyes. 388. 9780800242398.