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 syntheticprogestogen, 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 postcoitalhormonal contraceptive.[2][3][4]
Side effects[]
See also: Norethisterone § Side effects, and Progestin § Side effects
Pharmacology[]
See also: Norethisterone § 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]
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 syntheticestranesteroid 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 cyclopentylenol ethergroup has been attached at the C3 position and an acetateester has been attached at the C17β position.[1] Quingestanol acetate is the C17β acetateester 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]
^ abcdefGiannina 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 (New York, N.Y.). 131 (3): 781–9. doi:10.3181/00379727-131-33977. PMID5815452. S2CID12433167.
^ abcdeMischler TW, Rubio B, Larranaga A, Guiloff E, Moggia AV (March 1974). "Further experience with quingestanol acetate as a postcoital oral contraceptive". Contraception. 9 (3): 221–5. doi:10.1016/0010-7824(74)90013-4. PMID4613534.
^ abRaynaud JP, Ojasoo T (1986). "The design and use of sex-steroid antagonists". J. Steroid Biochem. 25 (5B): 811–33. doi:10.1016/0022-4731(86)90313-4. PMID3543501. Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).
^ abDi 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. PMID4853997.
Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites)