Topilutamide

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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 mass403.234 g/mol 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][3]

Available forms

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

Pharmacology

Pharmacodynamics

Topilutamide is a 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.
  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 i 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" (PDF). Drug Development Research. 59 (3): 292–306. doi:10.1002/ddr.10166. ISSN 0272-4391.
  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 Eucapil website
  9. ^ https://chem.nlm.nih.gov/chemidplus/rn/260980-89-0
  10. ^ http://www.who.int/medicines/publications/druginformation/innlists/PL91.pdf
  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.