Quingestanol

Quingestanol (INN, BAN), also known as norethisterone 3-cyclopentyl enol ether, is a progestin of the 19-nortestosterone group which was never marketed.[1] It is a prodrug of norethisterone.[2][3] An acylated derivative, quingestanol acetate, is used as a pharmaceutical drug.[1]

This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see quingestanol acetate.
Quingestanol
Clinical data
Other namesNorethisterone 3-cyclopentyl enol ether; 3-(Cyclopentyloxy)-17α-ethynylestra-3,5-dien-17β-ol
Drug classProgestin; Progestogen
ATC code
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-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.031.078
Chemical and physical data
FormulaC25H34O2
Molar mass366.545 g·mol−1
3D model (JSmol)
SMILES
  • O(\C4=C\C3=C\C[C@@H]2[C@H](CC[C@]1(C)[C@@](C#C)(O)CC[C@H]12)[C@H]3CC4)C5CCCC5
InChI
  • InChI=1S/C25H34O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,8,16,18,20-23,26H,4-7,9-15H2,2H3/t20-,21+,22+,23-,24-,25-/m0/s1
  • Key:PCJFRMOEZQQSAX-AIOSZGMZSA-N

See also

References
  1. Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1721. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
  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).
  3. 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.



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