Quingestanol acetate

Quingestanol acetate
Clinical data
Trade namesDemovis, Pilomin, others
Other namesW-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 classProgestogen; Progestin; Progestogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • [(8R,9S,10R,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-2,7,8,9,10,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.163
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Chemical and physical data
FormulaC27H36O3
Molar mass408.582 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O[C@@]5(C#C)CC[C@@H]4[C@]5(C)CC[C@@H]3[C@@H]2C(\C=C(\OC1CCCC1)CC2)=C/C[C@H]34)C
InChI
  • InChI=1S/C27H36O3/c1-4-27(30-18(2)28)16-14-25-24-11-9-19-17-21(29-20-7-5-6-8-20)10-12-22(19)23(24)13-15-26(25,27)3/h1,9,17,20,22-25H,5-8,10-16H2,2-3H3/t22-,23+,24+,25-,26-,27-/m0/s1
  • Key:FLGJKPPXEKYCBY-AKCFYGDASA-N

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. 1 2 3 4 5 6 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. 1 2 3 4 5 6 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 (New York, N.Y.). 131 (3): 781–9. doi:10.3181/00379727-131-33977. PMID 5815452. S2CID 12433167.
  3. 1 2 3 4 5 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. 1 2 3 4 5 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. 1 2 Raynaud 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. PMID 3543501. Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).
  6. 1 2 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. 1 2 3 Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7.
  8. 1 2 3 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. ISBN 9780800242398.
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