Estradiol butyrylacetate: Difference between revisions

Estradiol butyrylacetate
Clinical data
Trade names	Follikosid, Follikoside, Klimanosid
Other names	EBA; Estradiol 17β-butyrylacetate
Routes of; administration	Intramuscular injection
Identifiers
	IUPAC name [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 3-oxohexanoate;
CAS Number	60883-80-9;
PubChem CID	91667672;
ChemSpider	52084153;
UNII	6ADI485E6C;
CompTox Dashboard (EPA)	DTXSID301046408 ;
Chemical and physical data
Formula	C24H32O4
Molar mass	384.516 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(=O)CC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C;
	InChI InChI=1S/C24H32O4/c1-3-4-16(25)14-23(27)28-22-10-9-21-20-7-5-15-13-17(26)6-8-18(15)19(20)11-12-24(21,22)2/h6,8,13,19-22,26H,3-5,7,9-12,14H2,1-2H3/t19-,20-,21+,22+,24+/m1/s1; Key:LLWMXKOTHFASEO-NTYLBUJVSA-N;

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Revision as of 04:29, 9 June 2019

Estradiol butyrylacetate (EBA), sold under the brand names Follikosid and Klimanosid Depot (with testosterone caprinoylacetate), is an estrogen medication which is no longer marketed.^[1]^[2] It is an estrogen ester, specifically, an ester of estradiol.^[1] It is administered by intramuscular injection and a single 10 mg dose has been said to have a duration of action of 2 to 3 weeks.^[3] The excretion of EBA in women has been studied.^[4]^[5]

References

^ ^a ^b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.
^ Hans Hermann Julius Hager; Walther Kern; Paul Heinz List; Hermann Josef Roth (29 July 2013). Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL). Springer-Verlag. pp. 157–. ISBN 978-3-662-25655-8.
^ Heinrich Kahr (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 20–. ISBN 978-3-7091-5694-0.
^ Kaiser R (September 1961). "Die Östrogenausscheidung im Zyklus und nach Injektion von Östradiolestern. Ein Beitrag zur Therapie mit Depotöstrogenen" [Estrogen excretion during the cycle and after injection of estradiol esters. A contribution to therapy with depot estrogens]. Geburtshilfe Frauenheilkd (in German). 21: 868–78. ISSN 0016-5751. PMID 13750804.
^ Kaiser, R. "Über die Oestrogenausscheidung nach Injektion von Oestradiolestern" [Estrogen excretion after injection of estradiol esters]. Gewebs-und Neurohormone: Physiologie des Melanophorenhormons [Tissue and Neurohormones: Physiology of the Melanophore Hormone] (in German). Springer, Berlin, Heidelberg. pp. 227–232. doi:10.1007/978-3-642-86860-3_24. ISBN 978-3-540-02909-0.

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.

[HagerKern2013-2] Hans Hermann Julius Hager; Walther Kern; Paul Heinz List; Hermann Josef Roth (29 July 2013). Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL). Springer-Verlag. pp. 157–. ISBN 978-3-662-25655-8.

[Kahr2013-3] Heinrich Kahr (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 20–. ISBN 978-3-7091-5694-0.

[pmid13750804-4] Kaiser R (September 1961). "Die Östrogenausscheidung im Zyklus und nach Injektion von Östradiolestern. Ein Beitrag zur Therapie mit Depotöstrogenen" [Estrogen excretion during the cycle and after injection of estradiol esters. A contribution to therapy with depot estrogens]. Geburtshilfe Frauenheilkd (in German). 21: 868–78. ISSN 0016-5751. PMID 13750804.

[Kaiser1962-5] Kaiser, R. "Über die Oestrogenausscheidung nach Injektion von Oestradiolestern" [Estrogen excretion after injection of estradiol esters]. Gewebs-und Neurohormone: Physiologie des Melanophorenhormons [Tissue and Neurohormones: Physiology of the Melanophore Hormone] (in German). Springer, Berlin, Heidelberg. pp. 227–232. doi:10.1007/978-3-642-86860-3_24. ISBN 978-3-540-02909-0.

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@@ Line 5: / Line 5: @@
 | IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-17-yl] 3-oxohexanoate
 | image = Estradiol butyrylacetate.svg
-| width =
+| width = 250px
 <!--Clinical data-->
@@ Line 38: / Line 38: @@
 | ChemSpiderID = 52084153
 | UNII = 6ADI485E6C
-| synonyms = EBA
+| synonyms = EBA; Estradiol 17β-butyrylacetate
 <!--Chemical data-->
 | C=24 | H=32 | N= | O=4
-| molecular_weight =
+| molecular_weight = 384.516 g/mol
-| smiles = CCCC(=O)CC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
+| SMILES = CCCC(=O)CC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
 | StdInChI_Ref =
 | StdInChI = 1S/C24H32O4/c1-3-4-16(25)14-23(27)28-22-10-9-21-20-7-5-15-13-17(26)6-8-18(15)19(20)11-12-24(21,22)2/h6,8,13,19-22,26H,3-5,7,9-12,14H2,1-2H3/t19-,20-,21+,22+,24+/m1/s1
@@ Line 50: / Line 50: @@
 }}
-'''Estradiol butyrylacetate''' ('''EBA''') (brand names '''Follikosid''', '''Follikoside''', '''Klimanosid R-Depot''' (with [[testosterone caprinoylacetate]] and [[reserpine]]) is an [[estrogen (medication)|estrogen]] medication which is no longer marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA129|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=898}}</ref><ref name="HagerKern2013">{{cite book|author1=Hans Hermann Julius Hager|author2=Walther Kern|author3=Paul Heinz List|author4=Hermann Josef Roth|title=Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL)|url=https://books.google.com/books?id=a2a0BgAAQBAJ&pg=PA157|date=29 July 2013|publisher=Springer-Verlag|isbn=978-3-662-25655-8|pages=157–}}</ref> It is an [[estrogen ester]], specifically, an [[ester]] of [[estradiol]].<ref name="Elks2014" /> It is administered by [[intramuscular injection]] and a single 10&nbsp;mg dose has been said to have a [[duration of action]] of 2 to 3&nbsp;weeks.<ref name="Kahr2013">{{cite book|author=Heinrich Kahr|title=Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur|url=https://books.google.com/books?id=Hte1BgAAQBAJ&pg=PA20|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-7091-5694-0|pages=20–}}</ref>
+'''Estradiol butyrylacetate''' ('''EBA'''), sold under the brand names '''Follikosid''' and '''Klimanosid Depot''' (with [[testosterone caprinoylacetate]]), is an [[estrogen (medication)|estrogen]] medication which is no longer marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA129|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=898}}</ref><ref name="HagerKern2013">{{cite book|author1=Hans Hermann Julius Hager|author2=Walther Kern|author3=Paul Heinz List|author4=Hermann Josef Roth|title=Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL)|url=https://books.google.com/books?id=a2a0BgAAQBAJ&pg=PA157|date=29 July 2013|publisher=Springer-Verlag|isbn=978-3-662-25655-8|pages=157–}}</ref> It is an [[estrogen ester]], specifically, an [[ester]] of [[estradiol]].<ref name="Elks2014" /> It is administered by [[intramuscular injection]] and a single 10&nbsp;mg dose has been said to have a [[duration of action]] of 2 to 3&nbsp;weeks.<ref name="Kahr2013">{{cite book|author=Heinrich Kahr|title=Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur|url=https://books.google.com/books?id=Hte1BgAAQBAJ&pg=PA20|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-7091-5694-0|pages=20–}}</ref> The [[excretion]] of EBA in women has been studied.<ref name="pmid13750804">{{cite journal | vauthors = Kaiser R | title = Die Östrogenausscheidung im Zyklus und nach Injektion von Östradiolestern. Ein Beitrag zur Therapie mit Depotöstrogenen | trans-title = Estrogen excretion during the cycle and after injection of estradiol esters. A contribution to therapy with depot estrogens | language = German | journal = Geburtshilfe Frauenheilkd | volume = 21 | issue = | pages = 868–78 | date = September 1961 | issn = 0016-5751 | pmid = 13750804 | doi = | url = }}</ref><ref name="Kaiser1962">{{cite book | last1 = Kaiser | first1 = R | chapter = Über die Oestrogenausscheidung nach Injektion von Oestradiolestern | trans-chapter = Estrogen excretion after injection of estradiol esters | pages = 227–232 | doi = 10.1007/978-3-642-86860-3_24 | title = Gewebs-und Neurohormone: Physiologie des Melanophorenhormons | trans-title = Tissue and Neurohormones: Physiology of the Melanophore Hormone | language = German | publisher = Springer, Berlin, Heidelberg | isbn = 978-3-540-02909-0}}</ref>
 ==References==