Estradiol phenylpropionate

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
Drug class	Estrogen; Estrogen ester
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;

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 Garaffa G, Ralph DJ (12 February 2015). "Female to Male Transsexualism". In Mirone V (ed.). Clinical Uro-Andrology. Springer. pp. 17–. ISBN 978-3-662-45018-5.
^ ^a ^b Hager HH, Kern W, List PH, Roth HJ (29 July 2013). "Oestradiol". 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 A (1989). "Hormonpräparate, die zur Behandlung der Wechseljahre eingesetzt werden". Die Wechseljahre der Frau. pp. 153–164. doi:10.1007/978-3-0348-6676-7_11. ISBN 978-3-7643-1947-2.
^ "MIXOGEN® (Injection)". Archived from the original on 2016-05-30. Retrieved 2016-06-10.
^ Pschyrembeln W (15 June 2011). "Störungen in der Postmenopause". 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): 53–58. 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): 183–186. 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] Garaffa G, Ralph DJ (12 February 2015). "Female to Male Transsexualism". In Mirone V (ed.). Clinical Uro-Andrology. Springer. pp. 17–. ISBN 978-3-662-45018-5.

[HagerKern2013-3] Hager HH, Kern W, List PH, Roth HJ (29 July 2013). "Oestradiol". 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 A (1989). "Hormonpräparate, die zur Behandlung der Wechseljahre eingesetzt werden". Die Wechseljahre der Frau. pp. 153–164. doi:10.1007/978-3-0348-6676-7_11. ISBN 978-3-7643-1947-2.

[Intekom-5] "MIXOGEN® (Injection)". Archived from the original on 2016-05-30. Retrieved 2016-06-10.

[Pschyrembel2011-6] Pschyrembeln W (15 June 2011). "Störungen in der Postmenopause". 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): 53–58. 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): 183–186. doi:10.1016/0378-5122(81)90010-4. PMID 7289888.

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v t e Estradiol
Topics	Estradiol (as a hormone) Estradiol (as a medication) Pharmacodynamics of estradiol Pharmacokinetics of estradiol Estrogen (as a hormone) Estrogen (as a medication) Menopausal hormone therapy Feminizing hormone therapy Estradiol-containing birth control pill Combined injectable birth control High-dose estrogen Hydroxylation of estradiol
Esters	Estradiol acetate Estradiol acetylsalicylate Estradiol anthranilate Estradiol benzoate butyrate Estradiol benzoate cyclooctenyl ether Estradiol benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol diacetate Estradiol dibutyrate Estradiol dienantate Estradiol dipropionate Estradiol distearate Estradiol disulfate Estradiol diundecylate Estradiol diundecylenate Estradiol enantate Estradiol furoate Estradiol glucuronide Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol phenylpropionate Estradiol phosphate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol salicylate Estradiol stearate Estradiol sulfamate Estradiol sulfate Estradiol undecylate Estradiol undecylenate Estradiol valerate Estramustine phosphate (estradiol normustine phosphate) Estrogen ester Polyestradiol phosphate
Related	Estrone Estriol Estetrol Ethinylestradiol Conjugated estrogens Esterified estrogens Estrone sulfate Estropipate (piperazine estrone sulfate)

Estradiol phenylpropionate

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