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17β-Dihydroequilenin

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Chemical compound

Not to be confused with 17α-Dihydroequilin, 17β-Dihydroequilin, or 17α-Dihydroequilenin. Pharmaceutical compound
17β-Dihydroequilenin
Clinical data
Other namesβ-Dihydroequilenin; Δ-17β-Estradiol; 6,8-Didehydro-17β-estradiol; Estra-1,3,5(10),6,8-pentaen-3,17β-diol
Routes of
administration
By mouth
Drug classEstrogen
Identifiers
IUPAC name
  • (13S,14S,17S)-13-methyl-11,12,14,15,16,17-hexahydrocyclopentaphenanthrene-3,17-diol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H20O2
Molar mass268.356 g·mol
3D model (JSmol)
SMILES
  • C12CCC3=C(1CC2O)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-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). 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.

See also

References

  1. 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.
  2. 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.
Estrogens and antiestrogens
Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
See also
Estrogen receptor modulators
Androgens and antiandrogens
Progestogens and antiprogestogens
List of estrogens
Estrogen receptor modulators
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens


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