Estradiol monopropionate

Estradiol propionate (EP), also known as estradiol monopropionate or estradiol 17β-propionate and sold under the brand names Acrofollin, Akrofollin, and Follhormon, is an estrogen medication and estrogen ester which is no longer marketed.[1][2] It is the C17β propionate ester of estradiol.[1][2] EP was provided in an oil solution and was administered by intramuscular injection.[3][4][5][6] The medication was first marketed by 1938 or 1939.[7][8]

Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
Estrogen Other names RBA (%)a REP (%)b
ER ERα ERβ
Estradiol E2 100 100 100
Estradiol 3-sulfate E2S; E2-3S  ? 0.02 0.04
Estradiol 3-glucuronide E2-3G  ? 0.02 0.09
Estradiol 17β-glucuronide E2-17G  ? 0.002 0.0002
Estradiol benzoate EB; Estradiol 3-benzoate 10 1.1 0.52
Estradiol 17β-acetate E2-17A 31–45 24  ?
Estradiol diacetate EDA; Estradiol 3,17β-diacetate  ? 0.79  ?
Estradiol propionate EP; Estradiol 17β-propionate 19–26 2.6  ?
Estradiol valerate EV; Estradiol 17β-valerate 2–11 0.04–21  ?
Estradiol cypionate EC; Estradiol 17β-cypionate  ?c 4.0  ?
Estradiol palmitate Estradiol 17β-palmitate 0  ?  ?
Estradiol stearate Estradiol 17β-stearate 0  ?  ?
Estrone E1; 17-Ketoestradiol 11 5.3–38 14
Estrone sulfate E1S; Estrone 3-sulfate 2 0.004 0.002
Estrone glucuronide E1G; Estrone 3-glucuronide  ? <0.001 0.0006
Ethinylestradiol EE; 17α-Ethynylestradiol 100 17–150 129
Mestranol EE 3-methyl ether 1 1.3–8.2 0.16
Quinestrol EE 3-cyclopentyl ether  ? 0.37  ?
Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page.
Not to be confused with Estradiol 3-propionate or Estradiol dipropionate.
Estradiol monopropionate
Clinical data
Trade namesAcrofollin, Akrofollin, Follhormon
Other namesEP; Estradiol monopropionate; Estradiol propanoate; Estradiol 17β-propionate; Estradiol 17β-propanoate; Estra-1,3,5(10)-trien-3,17β-diol 17β-propionate
Routes of
administration		Intramuscular injection
Drug classEstrogen; 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] propanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.021.059
Chemical and physical data
FormulaC21H28O3
Molar mass328.452 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)O)C
InChI
  • InChI=1S/C21H28O3/c1-3-20(23)24-19-9-8-18-17-6-4-13-12-14(22)5-7-15(13)16(17)10-11-21(18,19)2/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19+,21+/m1/s1
  • Key:PQCRZWCSVWBYSC-AGRFSFNASA-N

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.
  2. Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 1967. ISBN 978-3-05-500156-7. Estra-1,3,5(10)-triene-3,17β-diol 17-propionate = 3,17β-Estradiol 17-monopropionate = (17β)-Estra-1,3,5(10)-triene-3,17-diol 17-propanoate (e) S Acrofollin, Akrofollin, Estradiol monopropionate, Follhormon "Saper", Ostradiolmonopropionat, Oestrolum propionicum U Estrogen
  3. United States. Department of the Treasury (1942). Treasury Decisions Under the Customs, Internal Revenue, and Other Laws: Including the Decisions of the Board of General Appraisers and the Court of Customs Appeals. U.S. Government Printing Office. p. 135. [...] T. D. 50714-C, covering akrofollin intramuscular oily solution of estrogenic hormone manufactured by Specific Pharmaceuticals, Inc., New York, N. Y., with the use of imported oestradiol-17-propionate crystals, [...]
  4. Csillag M, Vaczy L, Turr E (January 1951). "Apparent differences between the parenteral and intrauterine administration of estrogen substances". Gynaecologia. 131 (1): 9–18. doi:10.1159/000311707. PMID 14813560. For the following two groups we have chosen estradiol propionate (Akrofollin) in a dose of 3 X 5 mg. In each instance we performed biopsic strip-abrasion on the third day after the termination of intrauterine, resp. intramuscular hormone administration.
  5. Orosz M, Csapó I, Varga B (August 1983). "Alteration in the reactivity of hamster cheek pouch arterioles to prostaglandin E2 and noradrenaline during pregnancy or sex steroid treatment". Prostaglandins. 26 (2): 165–73. doi:10.1016/0090-6980(83)90085-0. PMID 6580678. [...] they were treated each second day with 0.2 ml sunflower oil, 0.2 mg/lOO g bw of oestradiol propionate (Akrofollin, Richter), [...]
  6. Wachnik A, Biró G, Biró L, Korom M, Gergely A, Antal M (1993). "Effect of sex hormones on copper, zinc, iron nutritional status and hepatic lipid peroxidation in rats". Die Nahrung. 37 (1): 28–34. doi:10.1002/food.19930370106. PMID 8464456. injected subcutaneously with oily solution of estradiol propionate (Acrofollin, Richter Gedeon)
  7. Boletín oficial de la propiedad industrial. Carasa y Cía. 1938. Fecha del Fecha de la solicitud de la marca: Abril 13, 1938. Certificado de propiedad: Octubre 23, 1939. Nombre y domicilio del concesionario: Chinoin Fábrica de Productos Farmacéuticos y Química S. A., Ujpest, Hungría. AKROFOLLIN.
  8. Dubrauszky V, St. Martzy (1941). "Die Wirkung natürlicher und künstlicher Brunststoffe im Tierversuch" [The effect of natural and artificial compounds in animal experiments]. Archiv für Gynäkologie. 171 (2): 242–253. doi:10.1007/BF01714680. ISSN 0003-9128. S2CID 9251783.


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