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Estrazinol

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Estrazinol
Identifiers

IUPAC name (1R,3aR,10bR,12aS)-1-ethynyl-8-methoxy-12a-methyl-1,2,3,3a,5,6,10b,11,12,12a-decahydrocyclopenta[5,6]pyrido[2,1-a]isoquinolin-1-ol
CAS Number	5941-36-6 15179-97-2 (HBr)
PubChem CID	10018368
ChemSpider	8193941
UNII	9KLU2E3573
ChEMBL	ChEMBL2110830
CompTox Dashboard (EPA)	DTXSID10208136
Chemical and physical data
Formula	C₂₀H₂₅NO₂
Molar mass	311.425 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC12CCC3C4=C(CCN3C1CCC2(C#C)O)C=C(C=C4)OC
InChI InChI=1S/C20H25NO2/c1-4-20(22)11-8-18-19(20,2)10-7-17-16-6-5-15(23-3)13-14(16)9-12-21(17)18/h1,5-6,13,17-18,22H,7-12H2,2-3H3/t17-,18-,19+,20+/m1/s1 Key:NTHOJXSFNBUDMY-ZRNYENFQSA-N

Estrazinol (INN), or as estrazinol hydrobromide (USAN) (developmental code name W-4454A), also known as 3-methoxy-8-aza-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, is a synthetic, steroidal estrogen that was synthesized in 1968 and further characterized in 1973 but was never marketed.^[1] It is described as a water-soluble estrogen.^[2]

References[edit]

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

^ Rassaert CL, DiPasquale G, Giannina T, Manning JP, Meli A (1973). "Estrogenic profile on a water-soluble estrogen, estrazinol hydrobromide". Steroids Lipids Res. 4 (5): 333–40. PMID 4368700.

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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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