Estrone benzoate

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.[1][2][3][4] It led to the development in 1933 of the more active estradiol benzoate, the first estradiol ester to be introduced for medical use.[5][6][7][8]

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 [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]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^−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]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

See also

• List of estrogen esters § Estrone esters

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.
2. A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 512–. ISBN 978-3-642-96158-8.
3. Parkes AS (February 1938). "Effective Absorption of Hormones". Br Med J. 1 (4024): 371–3. doi:10.1136/bmj.1.4024.371. PMC 2085798. PMID 20781252.
4. Butenandt, Adolf; Störmer, Inge (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.
5. Michael Oettel; Ekkehard Schillinger (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.
6. Miescher K, Scholz C, Tschopp E (1938). "The activation of female sex hormones: Mono-esters of alpha-oestradiol". Biochem. J. 32 (8): 1273–80. doi:10.1042/bj0321273b. PMC 1264184. PMID 16746750.
7. Enrique Raviña; Hugo Kubinyi (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.
8. 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): 2262–72. doi:10.1042/bj0302262. PMC 1263335. PMID 16746289.