Estrone benzoate

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;
Chemical and physical data
Formula	C25H26O3
Molar mass	374.48 g/mol 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;

Estrone benzoate, or estrone 3-benzoate, is a synthetic estrogen and estrogen ester – specifically, the C3 benzoate ester of estrone – which was discovered in 1931 and was never marketed.[1][2][3] It led to the development in 1933 and marketing in 1936 of the more active estradiol benzoate, the first estradiol ester to be introduced for medical use.[4][5][6][7]

References

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.
A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 512–. ISBN 978-3-642-96158-8.
Butenandt, A.; Hildebrandt, F. (1931). "Über ein zweites Hormonkrystallisat aus Schwangerenharn und seine physiologischen und chemischen Beziehungen zum krystallisierten Follikelhormon. [Untersuchungen über das weibliche Sexualhormon, 6. Mitteilung.]". Hoppe-Seyler's Zeitschrift für physiologische Chemie. 199 (4–6): 243–265. doi:10.1515/bchm2.1931.199.4-6.243. ISSN 0018-4888.
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.
Miescher K, Scholz C, Tschopp E (1938). "The activation of female sex hormones: Mono-esters of alpha-oestradiol". Biochem. J. 32 (8): 1273–80. PMC 1264184. PMID 16746750.
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.
Folley SJ (December 1936). "The effect of oestrogenic hormones on lactation and on the phosphatase of the blood and milk of the lactating cow" (PDF). The Biochemical Journal. 30 (12): 2262–72. doi:10.1042/bj0302262. PMC 1263335. PMID 16746289.

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[Elks2014-1] 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.

[Labhart2012-2] A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 512–. ISBN 978-3-642-96158-8.

[ButenandtHildebrandt1931-3] Butenandt, A.; Hildebrandt, F. (1931). "Über ein zweites Hormonkrystallisat aus Schwangerenharn und seine physiologischen und chemischen Beziehungen zum krystallisierten Follikelhormon. [Untersuchungen über das weibliche Sexualhormon, 6. Mitteilung.]". Hoppe-Seyler's Zeitschrift für physiologische Chemie. 199 (4–6): 243–265. doi:10.1515/bchm2.1931.199.4-6.243. ISSN 0018-4888.

[OettelSchillinger2012-4] 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.

[pmid16746750-5] Miescher K, Scholz C, Tschopp E (1938). "The activation of female sex hormones: Mono-esters of alpha-oestradiol". Biochem. J. 32 (8): 1273–80. PMC 1264184. PMID 16746750.

[RaviñaKubinyi2011-6] 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.

[pmid16746289-7] Folley SJ (December 1936). "The effect of oestrogenic hormones on lactation and on the phosphatase of the blood and milk of the lactating cow" (PDF). The Biochemical Journal. 30 (12): 2262–72. doi:10.1042/bj0302262. PMC 1263335. PMID 16746289.

Estrone benzoate

See also

References