Quingestrone

Quingestrone
Clinical data
Trade names	Enol-Luteovis
Other names	W-3399; Progesterone 3-cyclopentyl enol ether; PCPE; 3-Cyclopentyloxypregna-3,5-dien-20-one
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Progestogen ether; Neurosteroid
ATC code	G03A (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 1-[(8S,9S,10R,13S,14S,17S)-3-cyclopentyloxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone;
CAS Number	67-95-8;
PubChem CID	9929903;
ChemSpider	8105534;
UNII	0612VZ9I5Z;
KEGG	D05680;
ChEMBL	ChEMBL2104568;
CompTox Dashboard (EPA)	DTXSID00217196 ;
Chemical and physical data
Formula	C26H38O2
Molar mass	382.588 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(=C4)OC5CCCC5)C)C;
	InChI InChI=1S/C26H38O2/c1-17(27)22-10-11-23-21-9-8-18-16-20(28-19-6-4-5-7-19)12-14-25(18,2)24(21)13-15-26(22,23)3/h8,16,19,21-24H,4-7,9-15H2,1-3H3/t21-,22+,23-,24-,25-,26+/m0/s1; Key:XAVRSHOUEXATJE-FBQZJRKBSA-N;

Quingestrone, also known as progesterone 3-cyclopentyl enol ether (PCPE) and sold under the brand name Enol-Luteovis, is a progestin medication which was previously used in birth control pills in Italy but is now no longer marketed.^[1]^[2]^[3]^[4]^[5] It is taken by mouth.^[6]

Quingestrone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[1]^[7]^[8] It has weak glucocorticoid activity.^[9]^[10]^[11]

Quingestrone was introduced for medical use by 1962.^[6]^[12] It is no longer available.^[13]

^ ^a ^b Elks J, Ganellin CR, eds. (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 1058. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2085-3. OCLC 898564124.
^ International Planned Parenthood Federation. Medical Committee. Oral Advisory Group (1965). Handbook on oral contraception. Little, Brown. p. 18. OCLC 2717593.
^ Larrey D, Geneve J, Pessayre D, Machayekhi JP, Degott C, Benhamou JP (February 1987). "Prolonged cholestasis after cyproheptadine-induced acute hepatitis". Journal of Clinical Gastroenterology. 9 (1): 102–104. doi:10.1097/00004836-198702000-00026. PMID 3559100. She had been taking an oral contraceptive combining ethinylestradiol and quingestrone since 1980.
^ Hawkins DF (1974). Obstetric therapeutics: clinical pharmacology and therapeutics in obstetric practice. Baillière Tindall. pp. 129, 138, 145. ISBN 978-0-7020-0471-1.
^ Bentley PJ (1980). Endocrine Pharmacology: Physiological Basis and Therapeutic Applications. CUP Archive. pp. 274–. ISBN 978-0-521-22673-8.
^ ^a ^b Cite error: The named reference CurrentMedicineAndDrugs1962 was invoked but never defined (see the help page).
^ Cite error: The named reference CaieKlopper1964 was invoked but never defined (see the help page).
^ Cite error: The named reference MeliWolff1965 was invoked but never defined (see the help page).
^ Cite error: The named reference Martini1966 was invoked but never defined (see the help page).
^ Cite error: The named reference SteinetzBeach1965 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid4175595 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid13861933 was invoked but never defined (see the help page).
^ Cite error: The named reference Micromedex was invoked but never defined (see the help page).

[Elks2014-1] Elks J, Ganellin CR, eds. (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 1058. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2085-3. OCLC 898564124.

[Group1965-2] International Planned Parenthood Federation. Medical Committee. Oral Advisory Group (1965). Handbook on oral contraception. Little, Brown. p. 18. OCLC 2717593.

[pmid3559100-3] Larrey D, Geneve J, Pessayre D, Machayekhi JP, Degott C, Benhamou JP (February 1987). "Prolonged cholestasis after cyproheptadine-induced acute hepatitis". Journal of Clinical Gastroenterology. 9 (1): 102–104. doi:10.1097/00004836-198702000-00026. PMID 3559100. She had been taking an oral contraceptive combining ethinylestradiol and quingestrone since 1980.

[Hawkins1974-4] Hawkins DF (1974). Obstetric therapeutics: clinical pharmacology and therapeutics in obstetric practice. Baillière Tindall. pp. 129, 138, 145. ISBN 978-0-7020-0471-1.

[Bentley1980-5] Bentley PJ (1980). Endocrine Pharmacology: Physiological Basis and Therapeutic Applications. CUP Archive. pp. 274–. ISBN 978-0-521-22673-8.

[CurrentMedicineAndDrugs1962-6] Cite error: The named reference CurrentMedicineAndDrugs1962 was invoked but never defined (see the help page).

[CaieKlopper1964-7] Cite error: The named reference CaieKlopper1964 was invoked but never defined (see the help page).

[MeliWolff1965-8] Cite error: The named reference MeliWolff1965 was invoked but never defined (see the help page).

[Martini1966-9] Cite error: The named reference Martini1966 was invoked but never defined (see the help page).

[SteinetzBeach1965-10] Cite error: The named reference SteinetzBeach1965 was invoked but never defined (see the help page).

[pmid4175595-11] Cite error: The named reference pmid4175595 was invoked but never defined (see the help page).

[pmid13861933-12] Cite error: The named reference pmid13861933 was invoked but never defined (see the help page).

[Micromedex-13] Cite error: The named reference Micromedex was invoked but never defined (see the help page).

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Quingestrone

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