Quingestanol

This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see quingestanol acetate.

Quingestanol

Clinical data
Other names	Norethisterone 3-cyclopentyl enol ether; 3-(Cyclopentyloxy)-17α-ethynylestra-3,5-dien-17β-ol
Drug class	Progestin; Progestogen
ATC code	G03AC04 ( WHO ) G03AA02 ( WHO ) (with an estrogen)
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	10592-65-1
PubChem CID	9842127
ChemSpider	8017842
UNII	1A635076CE
CompTox Dashboard (EPA)	DTXSID80147422
ECHA InfoCard	100.031.078
Chemical and physical data
Formula	C25H34O2
Molar mass	366.545 g·mol−1
3D model (JSmol)	Interactive image
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

Quingestanol (INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name), 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]

See also

• List of progestogens

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.