Estradiol-17 β -cipionat

Structural formula
General
Surname	Estradiol-17 β -cipionat
other names	Depo-estradiol; Depofemin; Estradep; (17 β ) -3-hydroxyestra-1,3,5 (10) -trien-17-yl-3-cyclopentylpropanoate; 17 β -estradiol-17-cypionate;
Molecular formula	C 26 H 36 O 3
External identifiers / databases
EC number	206-237-8
ECHA InfoCard	100.005.672
PubChem	9403
ChemSpider	9033
DrugBank	DB13954
Wikidata	Q5401760
Drug information
Drug class	Estrogens
properties
Molar mass	396.56 g · mol -1
Physical state	firmly
density	1.2 ± 0.1 g / cm 3
Melting point	152 ° C
boiling point	532.8 ± 50.0 ° C
Vapor pressure	0.0 + 1.5 mmHg at 25 ° C
safety instructions
H and P phrases	H: 302-312-332-350-360
	P: 201-280-308 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Estradiol-17 β- cipionate is a synthetically produced derivative of the naturally occurring sex hormone estradiol . It is its 3-cyclopentylpropanoyl ester . The fixed combination of estradiol-17 β -cipionat with medroxyprogesterone , according to the World Health Organization list of essential medicines classified as important injectable contraceptives.

Estradiol-17 β -cipionate was introduced in 1952 by the Upjohn company in the USA for the pharmaceutical market. It is absorbed more slowly than estradiol. Compared to other intramuscularly used estradiol esters of estradiol-17 has β -cipionat the longest with 11 days duration of action. Estradiol benzoate and estradiol valerate , however, only have a duration of action of 4–5 and 7–8 days, respectively.

Individual evidence

↑ ^a ^b ^c ^d Entry on Estrofem in the ChemSpider database of the Royal Society of Chemistry , accessed on January 15, 2015.
↑ ^a ^b Data sheet β-Estradiol 17-cypionate from Sigma-Aldrich , accessed on January 15, 2015 ( PDF ).
^ RA Hill: Dictionary of Steroids. CRC Press, 1991, ISBN 978-0-412-27060-4 , p. 415 ( limited preview in Google book search).
^ Index Nominum 2000. Taylor & Francis, 2000, ISBN 978-3-887-63075-1 , p. 405 ( limited preview in Google book search).
^ Marshall Sittig: Pharmaceutical Manufacturing Encyclopedia. Noyes Publications, 1988, ISBN 978-0-815-51144-1 , pp. 575-576 ( limited preview in Google Book Search).
↑ Sriram: Medicinal Chemistry. Pearson Education India, 2007, ISBN 978-8-131-70031-0 , p. 427 ( limited preview in Google Book Search).
↑ Oriowo MA, Landgren BM, Stenström B, Diczfalusy E: A comparison of the pharmacokinetic properties of three estradiol esters . In: Contraception . 21, No. 4, April 1980, pp. 415-24. doi : 10.1016 / s0010-7824 (80) 80018-7 . PMID 7389356 .

[chemspider-1] Entry on Estrofem in the ChemSpider database of the Royal Society of Chemistry , accessed on January 15, 2015.

[sigma-2] Data sheet β-Estradiol 17-cypionate from Sigma-Aldrich , accessed on January 15, 2015 ( PDF ).

[Roberts1991-3] RA Hill: Dictionary of Steroids. CRC Press, 1991, ISBN 978-0-412-27060-4 , p. 415 ( limited preview in Google book search).

[Index_Nominum_2000:_International_Drug_Directory-4] Index Nominum 2000. Taylor & Francis, 2000, ISBN 978-3-887-63075-1 , p. 405 ( limited preview in Google book search).

[Sittig1988-5] Marshall Sittig: Pharmaceutical Manufacturing Encyclopedia. Noyes Publications, 1988, ISBN 978-0-815-51144-1 , pp. 575-576 ( limited preview in Google Book Search).

[Sriram-6] Sriram: Medicinal Chemistry. Pearson Education India, 2007, ISBN 978-8-131-70031-0 , p. 427 ( limited preview in Google Book Search).

[pmid7389356-7] Oriowo MA, Landgren BM, Stenström B, Diczfalusy E: A comparison of the pharmacokinetic properties of three estradiol esters . In: Contraception . 21, No. 4, April 1980, pp. 415-24. doi : 10.1016 / s0010-7824 (80) 80018-7 . PMID 7389356 .