Estriol dihexanoate - Misplaced Pages

Chemical compound Pharmaceutical compound

Estriol dihexanoate
Clinical data

Other names	Oestriol dihexanoate; Estriol 3,17β-dihexanoate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dihexanoate
Routes of administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name phenanthren-17-yl] hexanoate
CAS Number	104202-96-2
PubChem CID	128509
ChemSpider	113906
UNII	J2K5XW8K72
CompTox Dashboard (EPA)	DTXSID90908869
Chemical and physical data
Formula	C₃₀H₄₄O₅
Molar mass	484.677 g·mol
3D model (JSmol)	Interactive image
SMILES CCCCCC(=O)O1(C21(CC32CCC4=C3C=CC(=C4)OC(=O)CCCCC)C)O
InChI InChI=1S/C30H44O5/c1-4-6-8-10-27(32)34-21-13-15-22-20(18-21)12-14-24-23(22)16-17-30(3)25(24)19-26(31)29(30)35-28(33)11-9-7-5-2/h13,15,18,23-26,29,31H,4-12,14,16-17,19H2,1-3H3/t23-,24-,25+,26-,29+,30+/m1/s1 Key:ZOVABFBGAYSQTL-AECPDVIXSA-N

Estriol dihexanoate, or estriol 3,17β-dihexanoate, is a synthetic estrogen and estrogen ester – specifically, the C3 and C17β dihexanoate ester of estriol – which was first described in 1963 and was never marketed. Following a single intramuscular injection of 8.90 mg estriol dihexanoate (equivalent to 5.0 mg estriol) in an oil solution, peak levels of estriol occurred after 2.1 to 3.4 days, an elimination half-life of 187 to 221 hours was observed, and estriol levels remained elevated for up to 20 to 50 days. For comparison, the durations of estriol and estriol dipropionate were far shorter.

References

^ Kuhnz W, Blode H, Zimmermann H (6 December 2012). "Pharmacokinetics of exogenous natural and synthetic estrogens and antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 273–. ISBN 978-3-642-60107-1.
Tsuneda K, Yamada J, Yasuda K, Mori H (April 1963). "Preparation of some estriol esters". Chemical & Pharmaceutical Bulletin. 11 (4): 510–514. doi:10.1248/cpb.11.510. PMID 13994597.
^ Heithecker R, Aedo AR, Landgren BM, Cekan SZ (1991). "Plasma estriol levels after intramuscular injection of estriol and two of its esters". Hormone Research. 35 (6): 234–238. doi:10.1159/000181911. PMID 1819548.

Estrogen receptor modulators

ERTooltip Estrogen receptor

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
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

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

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See also

References