Equilenin

Equilenin
Clinical data
Other names	6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one
Routes of; administration	By mouth
Drug class	Estrogen
Identifiers
	IUPAC name (13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one;
CAS Number	517-09-9 ;
PubChem CID	444865;
DrugBank	DB03515 ;
ChemSpider	392668 ;
UNII	W8FTJ17C4J;
KEGG	C14303 ;
ChEBI	CHEBI:34739;
ChEMBL	ChEMBL225546 ;
CompTox Dashboard (EPA)	DTXSID2052156 ;
ECHA InfoCard	100.007.483
Chemical and physical data
Formula	C18H18O2
Molar mass	266.340 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4[C@]3(CCc1c(ccc2c1ccc(O)c2)[C@@H]3CC4)C;
	InChI InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1 ; Key:PDRGHUMCVRDZLQ-WMZOPIPTSA-N ;
	(what is this?) (verify)

Equilenin, also known as 6,8-didehydroestrone, as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one, is a naturally occurring steroidal estrogen obtained from the urine of pregnant mares.^[1]^[2] It is used as one of the components in conjugated estrogens (brand name Premarin).^[2] It was the first complex natural product to be fully synthesized, in work reported by 1940 by Bachmann and Wilds.^[3]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 494–. ISBN 978-1-4757-2085-3.
^ ^a ^b Fritz MA, Speroff L (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
^ Bachmann WE, Cole W, Wilds AL (1940). "The Total Synthesis of the Sex Hormone Equilenin and Its Stereoisomers". J. Am. Chem. Soc. 62 (4): 824–839. doi:10.1021/ja01861a036.

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 494–. ISBN 978-1-4757-2085-3.

[FritzSperoff2012-2] Fritz MA, Speroff L (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.

[TS-3] Bachmann WE, Cole W, Wilds AL (1940). "The Total Synthesis of the Sex Hormone Equilenin and Its Stereoisomers". J. Am. Chem. Soc. 62 (4): 824–839. doi:10.1021/ja01861a036.

[1]

[2]

[3]

Clinical data

Other names	6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one
Routes of administration	By mouth
Drug class	Estrogen
Identifiers
IUPAC name (13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one
CAS Number	517-09-9^Y
PubChem CID	444865
DrugBank	DB03515^Y
ChemSpider	392668^Y
UNII	W8FTJ17C4J
KEGG	C14303^Y
ChEBI	CHEBI:34739
ChEMBL	ChEMBL225546^Y
CompTox Dashboard (EPA)	DTXSID2052156
ECHA InfoCard	100.007.483
Chemical and physical data
Formula	C₁₈H₁₈O₂
Molar mass	266.340 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C4[C@]3(CCc1c(ccc2c1ccc(O)c2)[C@@H]3CC4)C
InChI InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1^Y Key:PDRGHUMCVRDZLQ-WMZOPIPTSA-N^Y
^NY (what is this?) (verify)