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]
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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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ECHA InfoCard | 100.019.163 |
Chemical and physical data | |
Formula | C27H36O3 |
Molar mass | 408.582 g·mol−1 |
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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]
Quingestanol acetate was used as an oral, once-a-month, or postcoital hormonal contraceptive.[2][3][4]
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]
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]
Quingestanol acetate was patented in 1963[7] and marketed in Italy in 1972.[8][9]
Quingestanol acetate is the generic name of the drug and its INN and USAN .[1]
Quingestanol acetate was marketed under the brand names Demovis, Pilomin, Riglovis, and Unovis.[1][7]
Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).