Jump to content

Topilutamide: Difference between revisions

Add links
From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
mNo edit summary
Tags: Reverted Visual edit
m Reverted edits by Fluridil-god (talk) to last revision by Monkbot: not providing a reliable source (WP:CITE, WP:RS)
Line 49: Line 49:
}}
}}


'''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.<ref name="SeligsonCampion2003">{{cite journal|last1=Seligson|first1=Allen L|last2=Campion|first2=Brian K|last3=Brown|first3=Jason W|last4=Terry|first4=Ron C|last5=Kucerova|first5=Renata|last6=Bienova|first6=Martina|last7=Hajduch|first7=Marian|last8=Sovak|first8=Milos|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}}</ref><ref name="pmid12174057">{{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 = Dermatol Surg | volume = 28 | issue = 8 | pages = 678–85 | year = 2002 | pmid = 12174057 | doi = 10.1046/j.1524-4725.2002.02017.x| s2cid = 36439600 }}</ref><ref name="HaberStough2006">{{cite book|author1=Robert S. Haber|author2=Dowling Bluford Stough|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–}}</ref><ref name="ScriptaMedica2006">{{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).}}</ref><ref name="AvramRogers2009">{{cite book|author1=Marc R. Avram|author2=Nicole E. Rogers|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–}}</ref><ref name="KirbyCarson2009">{{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–}}</ref> It is used as a [[topical medication]] and is applied to the [[scalp]].<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" /> Topilutamide belongs to a class of molecules called perfluoroacylamido-arylpropanamides.
'''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.<ref name="SeligsonCampion2003">{{cite journal|last1=Seligson|first1=Allen L|last2=Campion|first2=Brian K|last3=Brown|first3=Jason W|last4=Terry|first4=Ron C|last5=Kucerova|first5=Renata|last6=Bienova|first6=Martina|last7=Hajduch|first7=Marian|last8=Sovak|first8=Milos|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}}</ref><ref name="pmid12174057">{{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 = Dermatol Surg | volume = 28 | issue = 8 | pages = 678–85 | year = 2002 | pmid = 12174057 | doi = 10.1046/j.1524-4725.2002.02017.x| s2cid = 36439600 }}</ref><ref name="HaberStough2006">{{cite book|author1=Robert S. Haber|author2=Dowling Bluford Stough|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–}}</ref><ref name="ScriptaMedica2006">{{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).}}</ref><ref name="AvramRogers2009">{{cite book|author1=Marc R. Avram|author2=Nicole E. Rogers|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–}}</ref><ref name="KirbyCarson2009">{{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–}}</ref> It is used as a [[topical medication]] and is applied to the [[scalp]].<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" />


Topilutamide is a [[nonsteroidal antiandrogen]] (NSAA), or an [[receptor antagonist|antagonist]] of the [[androgen receptor]] (AR), the [[biological target]] of [[androgen]]s like [[testosterone]] and [[dihydrotestosterone]] (DHT).<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" />
Topilutamide is a [[nonsteroidal antiandrogen]] (NSAA), or an [[receptor antagonist|antagonist]] of the [[androgen receptor]] (AR), the [[biological target]] of [[androgen]]s like [[testosterone]] and [[dihydrotestosterone]] (DHT).<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" />


Topilutamide was introduced for medical use in 2003.<ref name="pmid16821162" /> It is marketed only in the [[Czech Republic]] and [[Slovakia]].<ref name="EucapilWebsite" /> The patent for Topilutamide expired in 2020.
Topilutamide was introduced for medical use in 2003.<ref name="pmid16821162" /> It is marketed only in the [[Czech Republic]] and [[Slovakia]].<ref name="EucapilWebsite" />


==Medical uses==
==Medical uses==
Line 64: Line 64:


===Pharmacodynamics===
===Pharmacodynamics===
Topilutamide is an [[receptor antagonist|antagonist]] of the AR, the [[biological target]] of [[androgen]]s like [[testosterone]] and DHT.<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" /> Fluridil binds to the androgen receptor with approximately a 15-fold higher affinity than more primitive NSAAs such as [[bicalutamide]] and [[hydroxyflutamide]], but more research is required to validate these findings.<ref name="SeligsonCampion2003" />
Topilutamide is an [[receptor antagonist|antagonist]] of the AR, the [[biological target]] of [[androgen]]s like [[testosterone]] and DHT.<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" />


===Pharmacokinetics===
===Pharmacokinetics===
Topilutamide is a [[topical medication]] and is applied to the [[scalp]].<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" /> Fluridil degrades in human serum at 37°C with a half-life of approximately 6 hours and is undetectable after 48 hours. <ref name="SeligsonCampion2003" /> Perfluoroacylamido-arylpropanamides decompose [[Hydrolysis|hydrolytically]] to BP-34 and their respective [[Perfluorocarboxylic acid|perfluorocarboxylic]] acid. <ref name="SeligsonCampion2003" />
Topilutamide is a [[topical medication]] and is applied to the [[scalp]].<ref name="pmid12174057" /><ref name="HaberStough2006" /><ref name="ScriptaMedica2006" /><ref name="AvramRogers2009" /><ref name="KirbyCarson2009" />


==Chemistry==
==Chemistry==

Revision as of 08:16, 19 June 2021

Not to be confused with Tolbutamide.
Topilutamide
Clinical data
Trade namesEucapil
Other namesFluridil; BP-766
Routes of
administration		Topical[1][2][3][4][5]
Drug classNonsteroidal antiandrogen
ATC code
  • None
Identifiers
  • 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-[(2,2,2-trifluoroacetyl)amino]propanamide
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.245.367 Edit this at Wikidata
Chemical and physical data
FormulaC13H11F6N3O5
Molar mass403.237 g·mol−1
3D model (JSmol)
  • C[C@@](CNC(=O)C(F)(F)F)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O
  • InChI=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
  • Key: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.[6][1][2][3][4][5] It is used as a topical medication and is applied to the scalp.[1][2][3][4][5]

Topilutamide is a nonsteroidal antiandrogen (NSAA), or an antagonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).[1][2][3][4][5]

Topilutamide was introduced for medical use in 2003.[7] It is marketed only in the Czech Republic and Slovakia.[8]

Medical uses

Topilutamide is used as a topical medication in the treatment of pattern hair loss in men and women.[1][2][3][4][5]

Available forms

As Eucapil, topilutamide is available as a 2% topical formulation intended for application to the scalp.[4]

Pharmacology

Pharmacodynamics

Topilutamide is an antagonist of the AR, the biological target of androgens like testosterone and DHT.[1][2][3][4][5]

Pharmacokinetics

Topilutamide is a topical medication and is applied to the scalp.[1][2][3][4][5]

Chemistry

Topilutamide is a nonsteroidal compound and is closely related to other NSAAs such as flutamide and bicalutamide.[7]

History

Topilutamide was introduced for medical use in 2003.[7]

Society and culture

Generic names

Topilutamide is the generic name of the drug and its INNTooltip International Nonproprietary Name.[9][10][11] It is also known more commonly as fluridil.[6] Topilutamide is also known by its former developmental code name BP-766.[6]

Brand names

Topilutamide is marketed by Interpharma Praha under the brand name Eucapil.[7][3]

Availability

Topilutamide is available only in Europe in the Czech Republic and Slovakia.[8]

See also

References

  1. ^ a b c d e f g Sovak M, Seligson AL, Kucerova R, Bienova M, Hajduch M, Bucek M (2002). "Fluridil, a rationally designed topical agent for androgenetic alopecia: first clinical experience". Dermatol Surg. 28 (8): 678–85. doi:10.1046/j.1524-4725.2002.02017.x. PMID 12174057. S2CID 36439600.
  2. ^ a b c d e f g Robert S. Haber; Dowling Bluford Stough (2006). Hair Transplantation. Elsevier Health Sciences. pp. 7–. ISBN 1-4160-3104-9.
  3. ^ a b c d e f g h Scripta Medica. 2006. pp. 45, 53–54. 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).
  4. ^ a b c d e f g h Marc R. Avram; Nicole E. Rogers (30 November 2009). Hair Transplantation. Cambridge University Press. pp. 11–. ISBN 978-1-139-48339-1.
  5. ^ a b c d e f g Kirby RS, Carson CC, Kirby MG, White A (29 January 2009). Men's Health, Third Edition. CRC Press. pp. 362–. ISBN 978-1-4398-0807-8.
  6. ^ a b c Seligson, Allen L; Campion, Brian K; Brown, Jason W; Terry, Ron C; Kucerova, Renata; Bienova, Martina; Hajduch, Marian; Sovak, Milos (2003). "Development of fluridil, a topical suppressor of the androgen receptor in androgenetic alopecia". Drug Development Research. 59 (3): 292–306. doi:10.1002/ddr.10166. ISSN 0272-4391. S2CID 98640343.
  7. ^ a b c d Hermkens PH, Kamp S, Lusher S, Veeneman GH (2006). "Non-steroidal steroid receptor modulators". IDrugs. 9 (7): 488–94. doi:10.2174/0929867053764671. PMID 16821162.
  8. ^ a b "Androgenetic Alopecia,Hair loss,Eucapil". www.eucapil.com.
  9. ^ Chambers, Michael. "ChemIDplus - 260980-89-0 - YCNCRLKXSLARFT-UHFFFAOYSA-N - Topilutamide [INN] - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
  10. ^ "Microsoft Word - final_PL91.doc" (PDF). Retrieved 2018-10-04.
  11. ^ United States International Trade Commission (2008). Modifications to the Harmonized Tariff Schedule of the United States to Implement the Dominican Republic-Central America-United States Free Trade Agreement With Respect to Costa Rica. DIANE Publishing. pp. 18–. ISBN 978-1-4578-1723-6.
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Topilutamide&oldid=1029324260"