topilutamide

{{Short description|Chemical compound}}

{{Distinguish|Tolbutamide}}

{{Drugbox

| Verifiedfields =

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| IUPAC_name = 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-[(2,2,2-trifluoroacetyl)amino]propanamide

| image = Topilutamide.svg

| width = 250px

| tradename = Eucapil

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| legal_status =

| routes_of_administration = Topical

| class = Nonsteroidal antiandrogen

| bioavailability =

| protein_bound =

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| CAS_number_Ref =

| CAS_number = 260980-89-0

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| ATC_prefix = None

| ATC_suffix =

| PubChem = 44147451

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| ChemSpiderID_Ref =

| ChemSpiderID = 8106619

| UNII = A8EU2FXY13

| synonyms = Fluridil; BP-766

| C=13 | H=11 | F=6 | N=3 | O=5

| SMILES = C[C@@](CNC(=O)C(F)(F)F)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O

| StdInChI = 1S/C13H11F6N3O5/c1-11(25,5-20-10(24)13(17,18)19)9(23)21-6-2-3-8(22(26)27)7(4-6)12(14,15)16/h2-4,25H,5H2,1H3,(H,20,24)(H,21,23)/t11-/m1/s1

| StdInChIKey = YCNCRLKXSLARFT-LLVKDONJSA-N

}}

Topilutamide, known more commonly as fluridil and sold under the brand name Eucapil, is an antiandrogen medication which is used in the treatment of pattern hair loss in men and women.{{cite journal| vauthors = Seligson AL, Campion BK, Brown JW, Terry RC, Kucerova R, Bienova M, Hajduch M, Sovak M |title=Development of fluridil, a topical suppressor of the androgen receptor in androgenetic alopecia|journal=Drug Development Research|volume=59|issue=3|year=2003|pages=292–306|issn=0272-4391|doi=10.1002/ddr.10166|s2cid=98640343|url=https://www.researchgate.net/publication/227651615}}{{cite journal | vauthors = Sovak M, Seligson AL, Kucerova R, Bienova M, Hajduch M, Bucek M | title = Fluridil, a rationally designed topical agent for androgenetic alopecia: first clinical experience | journal = Dermatologic Surgery | volume = 28 | issue = 8 | pages = 678–85 | date = August 2002 | pmid = 12174057 | doi = 10.1046/j.1524-4725.2002.02017.x | s2cid = 36439600 }}{{cite book| vauthors = Haber RS, Stough DB |title=Hair Transplantation|url=https://books.google.com/books?id=PXJMqrbk-fAC&pg=PA7|year=2006|publisher=Elsevier Health Sciences|isbn=1-4160-3104-9|pages=7–}}{{cite book|title=Scripta Medica|url=https://books.google.com/books?id=ynVRAQAAIAAJ|year=2006|pages=45, 53–54|quote=Fluridil was developed as a topical antiandrogen, suitable for the treatment of hyperandrogenic skin syndromes. The cosmetic product Eucapil® containing 2% fluridil in isopropanol was tested in women with AGA in a 9-month open study. [...] In a clinical study conducted at our facility, fluridil in solution (Eucapil®, Interpharma Praha, Czech Republic) has been shown to be effective and safe in the treatment of men with androgenetic alopecia (30, 31).}}{{cite book| vauthors = Avram MR, Rogers NE |title=Hair Transplantation|url=https://books.google.com/books?id=j1XF1bnABFcC&pg=PA11|date=30 November 2009|publisher=Cambridge University Press|isbn=978-1-139-48339-1|pages=11–}}{{cite book|vauthors=Kirby RS, Carson CC, Kirby MG, White A|title=Men's Health, Third Edition|url=https://books.google.com/books?id=e-NyCQAAQBAJ&pg=PA362|date=29 January 2009|publisher=CRC Press|isbn=978-1-4398-0807-8|pages=362–}} It is used as a topical medication and is applied to the scalp. Topilutamide belongs to a class of molecules known as perfluoroacylamido-arylpropanamides.

Topilutamide is a nonsteroidal antiandrogen (NSAA), or an antagonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).

Topilutamide was introduced for medical use in 2003. It is marketed only in the Czech Republic and Slovakia. The patent for Topilutamide expired in 2020.