Estrone benzoate - Misplaced Pages

Chemical compound Pharmaceutical compound

Estrone benzoate
Clinical data

Other names	Ketohydroxyestrin benzoate; Estra-1,3,5(10)-trien-3-ol-17-one 3-benzoate
Routes of administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name phenanthren-3-yl] benzoate
CAS Number	2393-53-5
PubChem CID	15818351
ChemSpider	18553608
UNII	O636LYL5W8
ChEMBL	ChEMBL1628207
CompTox Dashboard (EPA)	DTXSID00946752
Chemical and physical data
Formula	C₂₅H₂₆O₃
Molar mass	374.480 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(1CCC2=O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5
InChI InChI=1S/C25H26O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-22H,7,9,11-14H2,1H3/t20-,21-,22+,25+/m1/s1 Key:HKUKRSLIEVXDMS-APDHKMKFSA-N

Estrone benzoate, or estrone 3-benzoate, is a synthetic estrogen and estrogen ester – specifically, the C3 benzoate ester of estrone – which was first reported in 1932 and was never marketed. It led to the development in 1933 of the more active estradiol benzoate, the first estradiol ester to be introduced for medical use.

References

Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.
Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 512–. ISBN 978-3-642-96158-8.
Parkes AS (February 1938). "Effective Absorption of Hormones". British Medical Journal. 1 (4024): 371–373. doi:10.1136/bmj.1.4024.371. PMC 2085798. PMID 20781252.
Butenandt A, Störmer I (1932). "Über isomere Follikelhormone. Untersuchungen über das weibliche Sexualhormon, 7. Mitteilung" [About isomeric follicle hormones. Studies on the female sex hormone, 7th communication.]. Hoppe-Seyler's Zeitschrift für physiologische Chemie. 208 (4): 129–148. doi:10.1515/bchm2.1932.208.4.129. ISSN 0018-4888.
Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 8–. ISBN 978-3-642-58616-3.
Miescher K, Scholz C, Tschopp E (August 1938). "The activation of female sex hormones: Mono-esters of alpha-oestradiol". The Biochemical Journal. 32 (8): 1273–1280. doi:10.1042/bj0321273b. PMC 1264184. PMID 16746750.
Raviña E, Kubinyi H (16 May 2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 175. ISBN 978-3-527-32669-3. Retrieved 20 May 2012.
Folley SJ (December 1936). "The effect of oestrogenic hormones on lactation and on the phosphatase of the blood and milk of the lactating cow". The Biochemical Journal. 30 (12): 2262–2272. doi:10.1042/bj0302262. PMC 1263335. PMID 16746289.

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