Estradiol phenylpropionate: Difference between revisions

Estradiol phenylpropionate
Clinical data
Trade names	Menformon Prolongatum, Dimenformon Prolongatum, Lynandron Prolongatum
Other names	Estradiol phenpropionate; Estradiol benzenepropionate; Estradiol phenylpropanoate; Estradiol benzenepropanoate
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-phenylpropanoate;
CAS Number	26443-03-8;
PubChem CID	68577;
ChemSpider	61847;
UNII	LS956OGN6U;
ChEMBL	ChEMBL1974118;
CompTox Dashboard (EPA)	DTXSID00181040 ;
ECHA InfoCard	100.043.340
Chemical and physical data
Formula	C27H32O3
Molar mass	404.550 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC12CCC3C(C1CCC2OC(=O)CCC4=CC=CC=C4)CCC5=C3C=CC(=C5)O;
	InChI InChI=1S/C27H32O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,9,11,17,22-25,28H,7-8,10,12-16H2,1H3/t22-,23-,24+,25+,27+/m1/s1; Key:LQWSQQKTZLDGME-RYIFMDQWSA-N;

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Revision as of 07:09, 2 June 2019

Estradiol phenylpropionate (EPP), also known as estradiol 17β-phenylpropionate and sold under the brand name Menformon Prolongatum, is an estrogen which is no longer marketed.^[1]^[2]^[3] It is an estrogen ester, specifically the C17β phenylpropionate ester of estradiol.^[1] EPP has been marketed in combination with estradiol benzoate under the brand name Dimenformon Prolongatum in Europe and in combination with estradiol benzoate, testosterone propionate, testosterone phenylpropionate, and testosterone isocaproate under the brand names Mixogen, Estandron Prolongatum, and Lynandron Prolongatum (a balanced mixture of estradiol and testosterone esters) in menopausal hormone therapy.^[4]^[1]^[2]^[5]^[3]^[6]^[7] Both of these medication combinations are long-acting injectables indicated in hormone replacement therapy for women in menopause. Dimenformon Prolongatum has also been investigated as a single injection, "morning after" post-coital contraceptive, and is additionally used as a component of hormone replacement therapy for transgender women.^[2]

The pharmacokinetics of EPP in combination with estradiol benzoate have been studied.^[8]^[9]

References

^ ^a ^b ^c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1.
^ ^a ^b ^c Vincenzo Mirone (12 February 2015). Clinical Uro-Andrology. Springer. pp. 17–. ISBN 978-3-662-45018-5.
^ ^a ^b 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.
^ Saure, Arto (1989). "Hormonpräparate, die zur Behandlung der Wechseljahre eingesetzt werden": 153–164. doi:10.1007/978-3-0348-6676-7_11. {{cite journal}}: Cite journal requires |journal= (help)
^ http://home.intekom.com/pharm/donmed/mixogen.html
^ Willibald Pschyrembel (15 June 2011). Praktische Gynäkologie: für Studierende und Ärzte. Walter de Gruyter. pp. 533–. ISBN 978-3-11-150424-7.
^ Rote Liste: Verzeichnis pharmazeutischer Spezialpräparate. Editio Cantor. 1965. Lynandron Prolongatum ® (Organon -> O 70) Zus. 1 Ampulle zu 1 ml: 1 mg Oestradiolbenzoat, 4 mg Oestradiolphenylpropionat, 20 mg Testosteronpropionat, 40 mg Testosteronphenylpropionat, 40 mg Testosteronisocapronat.
^ Rauramo L, Punnonen R, Kaihola LH, Grönroos M (January 1980). "Serum oestrone, oestradiol and oestriol concentrations in castrated women during intramuscular oestradiol valerate and oestradiolbenzoate-oestradiolphenylpropionate therapy". Maturitas. 2 (1): 53–8. doi:10.1016/0378-5122(80)90060-2. PMID 7402086.
^ Rauramo L, Punnonen R, Grönroos M (August 1981). "Serum concentrations of oestrone, oestradiol and oestriol during various oestrogen treatments". Maturitas. 3 (2): 183–6. doi:10.1016/0378-5122(81)90010-4. PMID 7289888.

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[IndexNominum2000-1] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1.

[Mirone2015-2] Vincenzo Mirone (12 February 2015). Clinical Uro-Andrology. Springer. pp. 17–. ISBN 978-3-662-45018-5.

[HagerKern2013-3] 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.

[Saure1989-4] Saure, Arto (1989). "Hormonpräparate, die zur Behandlung der Wechseljahre eingesetzt werden": 153–164. doi:10.1007/978-3-0348-6676-7_11. {{cite journal}}: Cite journal requires |journal= (help)

[Intekom-5] ttp://home.intekom.com/pharm/donmed/mixogen.html

[Pschyrembel2011-6] Willibald Pschyrembel (15 June 2011). Praktische Gynäkologie: für Studierende und Ärzte. Walter de Gruyter. pp. 533–. ISBN 978-3-11-150424-7.

[EditioCantor1965-7] Rote Liste: Verzeichnis pharmazeutischer Spezialpräparate. Editio Cantor. 1965. Lynandron Prolongatum ® (Organon -> O 70) Zus. 1 Ampulle zu 1 ml: 1 mg Oestradiolbenzoat, 4 mg Oestradiolphenylpropionat, 20 mg Testosteronpropionat, 40 mg Testosteronphenylpropionat, 40 mg Testosteronisocapronat.

[pmid7402086-8] Rauramo L, Punnonen R, Kaihola LH, Grönroos M (January 1980). "Serum oestrone, oestradiol and oestriol concentrations in castrated women during intramuscular oestradiol valerate and oestradiolbenzoate-oestradiolphenylpropionate therapy". Maturitas. 2 (1): 53–8. doi:10.1016/0378-5122(80)90060-2. PMID 7402086.

[pmid7289888-9] Rauramo L, Punnonen R, Grönroos M (August 1981). "Serum concentrations of oestrone, oestradiol and oestriol during various oestrogen treatments". Maturitas. 3 (2): 183–6. doi:10.1016/0378-5122(81)90010-4. PMID 7289888.

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-'''Estradiol phenylpropionate''' ('''EPP'''), also known as '''estradiol 17β-phenylpropionate''' and sold under the brand name '''Menformon Prolongatum''', is an [[estrogen (medication)|estrogen]] which is no longer marketed.<ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA406|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=406–}}</ref><ref name="Mirone2015">{{cite book|author=Vincenzo Mirone|title=Clinical Uro-Andrology|url=https://books.google.com/books?id=1KynBgAAQBAJ&pg=PA17|date=12 February 2015|publisher=Springer|isbn=978-3-662-45018-5|pages=17–}}</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 the C17β [[phenylpropionate]] [[ester]] of [[estradiol (medication)|estradiol]].<ref name="IndexNominum2000" /> EPP has been marketed in combination with [[estradiol benzoate]] under the brand name '''Dimenformon Prolongatum''' in [[Europe]] and in combination with estradiol benzoate, [[testosterone propionate]], [[testosterone phenylpropionate]], and [[testosterone isocaproate]] under the brand names '''Mixogen''' and '''Lynandron Prolongatum''' (a balanced mixture of estradiol and [[testosterone (medication)|testosterone]] esters).<ref name="IndexNominum2000" /><ref name="Mirone2015" /><ref name="Intekom">http://home.intekom.com/pharm/donmed/mixogen.html</ref><ref name="HagerKern2013" /><ref name="Pschyrembel2011">{{cite book|author=Willibald Pschyrembel|title=Praktische Gynäkologie: für Studierende und Ärzte|url=https://books.google.com/books?id=vVaTnHDFzZ0C&pg=PA533|date=15 June 2011|publisher=Walter de Gruyter|isbn=978-3-11-150424-7|pages=533–}}</ref><ref name="EditioCantor1965">{{cite book|title=Rote Liste: Verzeichnis pharmazeutischer Spezialpräparate|url=https://books.google.com/books?id=myhtAAAAMAAJ|year=1965|publisher=Editio Cantor|quote=Lynandron Prolongatum ® (Organon -> O 70) Zus. 1 Ampulle zu 1 ml: 1 mg Oestradiolbenzoat, 4 mg Oestradiolphenylpropionat, 20 mg Testosteronpropionat, 40 mg Testosteronphenylpropionat, 40 mg Testosteronisocapronat.}}</ref> Both of these medication combinations are long-acting [[injectable]]s indicated in [[hormone replacement therapy (menopause)|hormone replacement therapy]] for women in [[menopause]]. Dimenformon Prolongatum has also been investigated as a single injection, "morning after" [[coitus|post-coital]] [[contraceptive]], and is additionally used as a component of [[hormone replacement therapy (male-to-female)|hormone replacement therapy]] for [[transgender women]].<ref name="Mirone2015" />
+'''Estradiol phenylpropionate''' ('''EPP'''), also known as '''estradiol 17β-phenylpropionate''' and sold under the brand name '''Menformon Prolongatum''', is an [[estrogen (medication)|estrogen]] which is no longer marketed.<ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA406|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=406–}}</ref><ref name="Mirone2015">{{cite book|author=Vincenzo Mirone|title=Clinical Uro-Andrology|url=https://books.google.com/books?id=1KynBgAAQBAJ&pg=PA17|date=12 February 2015|publisher=Springer|isbn=978-3-662-45018-5|pages=17–}}</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 the C17β [[phenylpropionate]] [[ester]] of [[estradiol (medication)|estradiol]].<ref name="IndexNominum2000" /> EPP has been marketed in combination with [[estradiol benzoate]] under the brand name '''Dimenformon Prolongatum''' in [[Europe]] and in combination with estradiol benzoate, [[testosterone propionate]], [[testosterone phenylpropionate]], and [[testosterone isocaproate]] under the brand names '''Mixogen''', '''Estandron Prolongatum''', and '''Lynandron Prolongatum''' (a balanced mixture of estradiol and [[testosterone (medication)|testosterone]] esters) in [[menopausal hormone therapy]].<ref name="Saure1989">{{cite journal|last1=Saure|first1=Arto|title=Hormonpräparate, die zur Behandlung der Wechseljahre eingesetzt werden|year=1989|pages=153–164|doi=10.1007/978-3-0348-6676-7_11}}</ref><ref name="IndexNominum2000" /><ref name="Mirone2015" /><ref name="Intekom">http://home.intekom.com/pharm/donmed/mixogen.html</ref><ref name="HagerKern2013" /><ref name="Pschyrembel2011">{{cite book|author=Willibald Pschyrembel|title=Praktische Gynäkologie: für Studierende und Ärzte|url=https://books.google.com/books?id=vVaTnHDFzZ0C&pg=PA533|date=15 June 2011|publisher=Walter de Gruyter|isbn=978-3-11-150424-7|pages=533–}}</ref><ref name="EditioCantor1965">{{cite book|title=Rote Liste: Verzeichnis pharmazeutischer Spezialpräparate|url=https://books.google.com/books?id=myhtAAAAMAAJ|year=1965|publisher=Editio Cantor|quote=Lynandron Prolongatum ® (Organon -> O 70) Zus. 1 Ampulle zu 1 ml: 1 mg Oestradiolbenzoat, 4 mg Oestradiolphenylpropionat, 20 mg Testosteronpropionat, 40 mg Testosteronphenylpropionat, 40 mg Testosteronisocapronat.}}</ref> Both of these medication combinations are long-acting [[injectable]]s indicated in [[hormone replacement therapy (menopause)|hormone replacement therapy]] for women in [[menopause]]. Dimenformon Prolongatum has also been investigated as a single injection, "morning after" [[coitus|post-coital]] [[contraceptive]], and is additionally used as a component of [[hormone replacement therapy (male-to-female)|hormone replacement therapy]] for [[transgender women]].<ref name="Mirone2015" />
 The [[pharmacokinetics]] of EPP in combination with estradiol benzoate have been studied.<ref name="pmid7402086">{{cite journal | vauthors = Rauramo L, Punnonen R, Kaihola LH, Grönroos M | title = Serum oestrone, oestradiol and oestriol concentrations in castrated women during intramuscular oestradiol valerate and oestradiolbenzoate-oestradiolphenylpropionate therapy | journal = Maturitas | volume = 2 | issue = 1 | pages = 53–8 | date = January 1980 | pmid = 7402086 | doi = 10.1016/0378-5122(80)90060-2 | url = }}</ref><ref name="pmid7289888">{{cite journal | vauthors = Rauramo L, Punnonen R, Grönroos M | title = Serum concentrations of oestrone, oestradiol and oestriol during various oestrogen treatments | journal = Maturitas | volume = 3 | issue = 2 | pages = 183–6 | date = August 1981 | pmid = 7289888 | doi = 10.1016/0378-5122(81)90010-4 | url = }}</ref>

Revision as of 07:09, 2 June 2019

See also

References