Quingestanol

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 (INNTooltip International Nonproprietary Name, BANTooltip 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]

References

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