Quingestanol acetate

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Quingestanol acetate
Quingestanol acetate.svg
Clinical data
Trade names Demovis, Pilomin, Riglovis, Unovis
Synonyms W-4540; Norethisterone acetate 3-cyclopentyl enol ether; (17β)-3-(Cyclopentyloxy)-17-ethynylestra-3,5-dien-17-yl acetate
Routes of
administration
By mouth
Drug class Progestogen; Progestogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
ECHA InfoCard 100.019.163
Chemical and physical data
Formula C27H36O3
Molar mass 408.573 g/mol
3D model (JSmol)

Quingestanol acetate (INN, USAN) (brand names Demovis, Pilomin, Riglovis, Unovis), also known as norethisterone acetate 3-cyclopentyl enol ether, is a progestin of the 19-nortestosterone group with additional weak androgenic and estrogenic activity which is used as an oral, once-a-month, or postcoital hormonal contraceptive.[1][2][3][4] It is a prodrug of norethisterone, with both quingestanol and norethisterone acetate serving as intermediates in the transformation.[5][6] The drug was patented in 1963[7] and marketed in Italy in 1972.[8][9]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ Mischler 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. PMID 4613534. 
  4. ^ Donde UM, Virkar KD (June 1975). "Biochemical studies with once-a-month contraceptive pill containing quinestrol-quingestanol acetate". Contraception. 11 (6): 681–8. doi:10.1016/0010-7824(75)90065-7. PMID 1137940. 
  5. ^ Raynaud JP, Ojasoo T (1986). "The design and use of sex-steroid antagonists". J. Steroid Biochem. 25 (5B): 811–33. PMID 3543501. 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 (1974). "Quingestanol acetate metabolism in women". Pharmacology. 11 (5): 287–303. doi:10.1159/000136501. PMID 4853997. 
  7. ^ Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7. 
  8. ^ Population Reports: Oral contraceptives. Department of Medical and Public Affairs, George Washington Univ. Medical Center. 1975. p. A-64. 
  9. ^ Janne S. Kowalski (1 August 1988). Drug companies & products world guide. Sittig & Noyes. p. 388.