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Estrofurate

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Estrofurate
Identifiers

IUPAC name [(9S,13S,14S,17S)-17-(furan-3-yl)-17-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-yl] acetate
CAS Number	10322-73-3
PubChem CID	66360
ChemSpider	59738
UNII	0CDE7T54KW
KEGG	D04069
ChEMBL	ChEMBL2104224
CompTox Dashboard (EPA)	DTXSID60883114
Chemical and physical data
Formula	C₂₄H₂₆O₄
Molar mass	378.468 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3=CC2)CCC4(C5=COC=C5)O)C
InChI InChI=1S/C24H26O4/c1-15(25)28-18-4-6-19-16(13-18)3-5-21-20(19)7-10-23(2)22(21)8-11-24(23,26)17-9-12-27-14-17/h4-6,9,12-14,20,22,26H,3,7-8,10-11H2,1-2H3/t20-,22+,23+,24-/m1/s1 Key:AEVUURWLDCELOV-AYVPJYCDSA-N

Estrofurate (INN, USAN) (developmental code name AY-11483), also known as 17α-(3-furyl)-estra-1,3,5(10),7-tetraene-3,17-diol 3-acetate, is a synthetic, steroidal estrogen that was synthesized in 1967 and studied in the late 1960s and early 1970s but was never marketed.^[1]^[2] It is a relatively weak estrogen in bioassays.^[3]

References[edit]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 503. ISBN 978-1-4757-2085-3.

^ Banik UK, Revesz C, Herr F (April 1969). "Orally active oestrogens and progestins in prevention of pregnancy in rats". Journal of Reproduction and Fertility. 18 (3): 509–15. doi:10.1530/jrf.0.0180509. PMID 4182486.

^ Revesz C, Banik UK, Lefebvre Y (June 1970). "AY-11483, a new type of orally active oestrogen". Journal of Reproduction and Fertility. 22 (1): 27–32. doi:10.1530/jrf.0.0220027. PMID 5421116.

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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

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