17β-Dihydroequilenin

17β-Dihydroequilenin
Clinical data
Other names	β-Dihydroequilenin; Δ6,8-17β-Estradiol; 6,8-Didehydro-17β-estradiol; Estra-1,3,5(10),6,8-pentaen-3,17β-diol
Routes of; administration	By mouth
Drug class	Estrogen
Identifiers
	IUPAC name (13S,14S,17S)-13-methyl-11,12,14,15,16,17-hexahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	1423-97-8;
PubChem CID	3032407;
ChemSpider	2297390;
ChEMBL	ChEMBL123405;
CompTox Dashboard (EPA)	DTXSID40931405 ;
Chemical and physical data
Formula	C18H20O2
Molar mass	268.356 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CCC3=C([C@@H]1CC[C@@H]2O)C=CC4=C3C=CC(=C4)O;
	InChI InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16-17,19-20H,6-9H2,1H3/t16-,17-,18-/m0/s1; Key:RYWZPRVUQHMJFF-BZSNNMDCSA-N;

17β-Dihydroequilenin, or β-dihydroequilenin, also known as δ^6,8-17β-estradiol or 6,8-didehydro-17β-estradiol, as well as estra-1,3,5(10),6,8-pentaen-3,17β-diol, is a naturally occurring steroidal estrogen found in horses which is closely related to equilin, equilenin, and estradiol, and, as the 3-sulfate ester sodium salt, is a minor constituent (0.5%) of conjugated estrogens (Premarin).^[1] 17β-Dihydroequilenin has unexpectedly shown a selective estrogen receptor modulator (SERM)-like profile of estrogenic activity in studies with monkeys, in which beneficial effects on bone and the cardiovascular system were noted but proliferative responses in breast and endometrium were not observed.^[2]

References

^ Fritz MA, Speroff L (28 March 2012). "Postmenopausal Hormone Therapy". Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
^ Cline JM (April 2007). "Assessing the mammary gland of nonhuman primates: effects of endogenous hormones and exogenous hormonal agents and growth factors". Birth Defects Research. Part B, Developmental and Reproductive Toxicology. 80 (2): 126–146. doi:10.1002/bdrb.20112. PMID 17443713.

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Clinical data

Other names	β-Dihydroequilenin; Δ^6,8-17β-Estradiol; 6,8-Didehydro-17β-estradiol; Estra-1,3,5(10),6,8-pentaen-3,17β-diol
Routes of administration	By mouth
Drug class	Estrogen
Identifiers
IUPAC name (13S,14S,17S)-13-methyl-11,12,14,15,16,17-hexahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number	1423-97-8
PubChem CID	3032407
ChemSpider	2297390
ChEMBL	ChEMBL123405
CompTox Dashboard (EPA)	DTXSID40931405
Chemical and physical data
Formula	C₁₈H₂₀O₂
Molar mass	268.356 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC3=C([C@@H]1CC[C@@H]2O)C=CC4=C3C=CC(=C4)O
InChI InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16-17,19-20H,6-9H2,1H3/t16-,17-,18-/m0/s1 Key:RYWZPRVUQHMJFF-BZSNNMDCSA-N