Estradiol phenylpropionate

Chemical compound
Estradiol phenylpropionate
Clinical data
Trade namesMenformon Prolongatum, Dimenformon Prolongatum, Lynandron Prolongatum
Other namesEstradiol phenpropionate; Estradiol benzenepropionate; Estradiol phenylpropanoate; Estradiol benzenepropanoate
Routes of
administration
Intramuscular injection
Drug classEstrogen; Estrogen ester
Identifiers
  • [(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 Edit this at Wikidata
ECHA InfoCard100.043.340 Edit this at Wikidata
Chemical and physical data
FormulaC27H32O3
Molar mass404.550 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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]

See also

References

  1. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1.
  2. ^ 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.
  3. ^ 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.
  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.
  5. ^ "MIXOGEN® (Injection)". Archived from the original on 2016-05-30. Retrieved 2016-06-10.
  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.
  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.
  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.
  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.
  • v
  • t
  • e
TopicsEsters
Related
  • v
  • t
  • e
Estrogens and antiestrogens
Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
See also
Estrogen receptor modulators
Androgens and antiandrogens
Progestogens and antiprogestogens
List of estrogens
  • v
  • t
  • e
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
Stub icon

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e
Stub icon

This article about a steroid is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e