fispemifene

{{Short description|Chemical compound}}

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| IUPAC_name = 2-(2-(4-((1Z)-4-Chloro-1,2-diphenylbut-1-enyl)phenoxy)ethoxy)ethanol

| image = Fispemifene.svg

| width = 250

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| CAS_number = 341524-89-8

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| PubChem = 9954033

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| ChemSpiderID = 8129643

| UNII = 3VZ2833V08

| KEGG = D10008

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| ChEMBL = 2107341

| C=26 | H=27 | Cl=1 | O=3

| SMILES = C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCOCCO)/CCCl

| StdInChI_Ref =

| StdInChI = 1S/C26H27ClO3/c27-16-15-25(21-7-3-1-4-8-21)26(22-9-5-2-6-10-22)23-11-13-24(14-12-23)30-20-19-29-18-17-28/h1-14,28H,15-20H2/b26-25-

| StdInChIKey_Ref =

| StdInChIKey = NKZTZAQIKKGTDB-QPLCGJKRSA-N

| synonyms = HM-101

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Fispemifene (INN, USAN) (developmental code name HM-101) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was developed for the treatment of male hypogonadism but was abandoned and never marketed.{{Cite web |title=Fispemifene |url=https://adisinsight.springer.com/drugs/800013715 |website=AdisInsight |publisher=Springer Nature Switzerland AG}}{{Cite book |url=https://books.google.com/books?id=heJDAAAAQBAJ&pg=PA52 |title=Selective Estrogen Receptor Modulators: A New Brand of Multitarget Drugs |vauthors=Cano A, Calaf i Alsina J, Duenas-Diez JL |date=22 September 2006 |publisher=Springer Science & Business Media |isbn=978-3-540-34742-2 |pages=52–}}{{Cite book |url=https://books.google.com/books?id=iATfLbPgRugC&pg=PA90 |title=Nuclear Receptors as Drug Targets |vauthors=Ottow E, Weinmann H |date=8 September 2008 |publisher=John Wiley & Sons |isbn=978-3-527-62330-3 |pages=90–}} It reached phase II clinical trials for this indication before development was terminated in March 2016. The drug failed to achieve statistical significance on key effectiveness endpoints in clinical trials and was discontinued by its developer for strategic reasons.