Estradiol monopropionate

{{Short description|Chemical compound}}

{{Distinguish|Estradiol 3-propionate|Estradiol dipropionate}}

{{Drugbox

| Verifiedfields =

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| 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

| image = Estradiol monopropionate.svg

| width = 250px

| tradename = Acrofollin, Akrofollin, Follhormon

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| routes_of_administration = Intramuscular injection

| class = Estrogen; Estrogen ester

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| CAS_number_Ref =

| CAS_number = 3758-34-7

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| PubChem = 19571

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| ChemSpiderID_Ref =

| ChemSpiderID = 18438

| UNII = K31PC34297

| synonyms = EP; Estradiol monopropionate; Estradiol propanoate; Estradiol 17β-propionate; Estradiol 17β-propanoate; Estra-1,3,5(10)-trien-3,17β-diol 17β-propionate

| C=21 | H=28 | N= | O=3

| SMILES = CCC(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)O)C

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = PQCRZWCSVWBYSC-AGRFSFNASA-N

}}

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.{{cite book| vauthors = Elks J |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}}{{cite book| first = Martin | last = Negwer | name-list-style = vanc |title=Organic-chemical Drugs and Their Synonyms: (an International Survey)|url=https://books.google.com/books?id=ywltAAAAMAAJ|year=1994|publisher=Akademie Verlag|isbn=978-3-05-500156-7|page=1967|quote=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}} It is the C17β propionate ester of estradiol. EP was provided in an oil solution and was administered by intramuscular injection.{{cite book|author=United States. Department of the Treasury|title=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|url=https://books.google.com/books?id=nz3atjVOy5wC|year=1942|publisher=U.S. Government Printing Office|page=135|quote=[...] 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, [...]}}{{cite journal | vauthors = Csillag M, Vaczy L, Turr E | title = Apparent differences between the parenteral and intrauterine administration of estrogen substances | journal = Gynaecologia | volume = 131 | issue = 1 | pages = 9–18 | date = January 1951 | pmid = 14813560 | doi = 10.1159/000311707 | quote = 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. }}{{cite journal | vauthors = Orosz M, Csapó I, Varga B | title = Alteration in the reactivity of hamster cheek pouch arterioles to prostaglandin E2 and noradrenaline during pregnancy or sex steroid treatment | journal = Prostaglandins | volume = 26 | issue = 2 | pages = 165–73 | date = August 1983 | pmid = 6580678 | doi = 10.1016/0090-6980(83)90085-0 | quote = [...] they were treated each second day with 0.2 ml sunflower oil, 0.2 mg/lOO g bw of oestradiol propionate (Akrofollin, Richter), [...] }}{{cite journal | vauthors = Wachnik A, Biró G, Biró L, Korom M, Gergely A, Antal M | title = Effect of sex hormones on copper, zinc, iron nutritional status and hepatic lipid peroxidation in rats | journal = Die Nahrung | volume = 37 | issue = 1 | pages = 28–34 | year = 1993 | pmid = 8464456 | doi = 10.1002/food.19930370106 | quote = injected subcutaneously with oily solution of estradiol propionate (Acrofollin, Richter Gedeon) }} The medication was first marketed by 1938 or 1939.{{cite book|title=Boletín oficial de la propiedad industrial|url=https://books.google.com/books?id=S7Gjg0GUIRUC|year=1938|publisher=Carasa y Cía.|quote=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.}}{{cite journal| vauthors = Dubrauszky V, ((St. Martzy)) |title=Die Wirkung natürlicher und künstlicher Brunststoffe im Tierversuch|trans-title=The effect of natural and artificial compounds in animal experiments|journal=Archiv für Gynäkologie|volume=171|issue=2|year=1941|pages=242–253|issn=0003-9128|doi=10.1007/BF01714680|s2cid=9251783}}

{{Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors}}