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WAY-166818

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WAY-166818
Identifiers

IUPAC name 2-(4-Hydroxyphenyl)-1,3-benzoxazol-5-ol
ChemSpider	11193037
UNII	9R07VD5I9B
ChEMBL	ChEMBL187392
Chemical and physical data
Formula	C₁₃H₉NO₃
Molar mass	227.219 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC1=CC=C(C=C1)C1=NC2=CC(O)=CC=C2O1
InChI InChI=1S/C13H9NO3/c15-9-3-1-8(2-4-9)13-14-11-7-10(16)5-6-12(11)17-13/h1-7,15-16H Key:DPAMLAKLEWYMGF-UHFFFAOYSA-N

WAY-166818 is a synthetic, nonsteroidal estrogen related to WAY-200070 which is used in scientific research.^[1]^[2] It acts as a highly selective full agonist of the ERβ, with 57- and 164-fold selectivity for the ERβ over the ERα in the rat and mouse, respectively.^[1]^[2] At the human ERβ and ERα, WAY-166818 has IC₅₀ values of 29 nM and 1227 nM (25-fold difference), respectively.^[1] The compound has been verified to cross the blood-brain-barrier in rodents.^[1]^[2]

See also[edit]

References[edit]

^ ^a ^b ^c ^d Malamas MS, Manas ES, McDevitt RE, Gunawan I, Xu ZB, Collini MD, Miller CP, Dinh T, Henderson RA, Keith JC, Harris HA (2004). "Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-beta ligands". J. Med. Chem. 47 (21): 5021–40. doi:10.1021/jm049719y. PMID 15456246.

^ ^a ^b ^c Merchenthaler I, Hoffman GE, Lane MV (2005). "Estrogen and estrogen receptor-{beta} (ER{beta})-selective ligands induce galanin expression within gonadotropin hormone-releasing hormone-immunoreactive neurons in the female rat brain". Endocrinology. 146 (6): 2760–5. doi:10.1210/en.2004-1562. PMID 15790727.

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Estrogen receptor modulators

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMs)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

Agonists

Antagonists

Unknown

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

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