Estrapronicate

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(8R,9S,13S,14S,17S)-13-Methyl-3-propanoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] pyridine-3-carboxylate

| image = Estrapronicate.svg

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| routes_of_administration = Intramuscular injection

| class = Estrogen; Estrogen ester

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| CAS_number = 4140-20-9

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = BC621AC03L

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| PubChem = 66433

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| ChemSpiderID = 59806

| synonyms = Estradiol propionicotinate; Estradiol propionate nicotinate; Estradiol nicotinate propionate; Estradiol 17β-nicotinate 3-propionate

| C=27 | H=31 | N=1 | O=4

| SMILES = CCC(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4OC(=O)C5=CN=CC=C5)C

| StdInChI = 1S/C27H31NO4/c1-3-25(29)31-19-7-9-20-17(15-19)6-8-22-21(20)12-13-27(2)23(22)10-11-24(27)32-26(30)18-5-4-14-28-16-18/h4-5,7,9,14-16,21-24H,3,6,8,10-13H2,1-2H3/t21-,22-,23+,24+,27+/m1/s1

| StdInChIKey = FXMSQUVSUXBBAB-TXDQRGGKSA-N

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Estrapronicate ({{abbrlink|INN|International Nonproprietary Name}}), also known as estradiol nicotinate propionate is an estrogen medication and estrogen ester which was never 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=PA898|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=898–}} It was studied as a component of the experimental tristeroid combination drug Trophobolene, which contained nandrolone decanoate, estrapronicate, and hydroxyprogesterone heptanoate.{{cite book|title=Excerpta medica. Section 8, Neurology and neurosurgery|url=https://books.google.com/books?id=_qiaAAAAIAAJ|year=1981|page=10}}{{cite book|title=Testosterone Congeners—Advances in Research and Application: 2013 Edition: ScholarlyBrief|url=https://books.google.com/books?id=CR-NH3HzlSkC&pg=PA137|date=21 June 2013|publisher=ScholarlyEditions|isbn=978-1-4816-9288-5|pages=137–}}