Topilutamide
Template:Short description Script error: No such module "Distinguish". Template:Short description Page Template:Infobox drug/styles.css has no content.
Page Module:Infobox/styles.css has no content.
| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Clinical data | |
|---|---|
| Trade names | Eucapil |
| Other names | Fluridil; BP-766 |
| Routes of administration | Topical[1][2][3][4][5] |
| Drug class | Nonsteroidal antiandrogen |
| ATC code | Page Template:Plainlist/styles.css has no content.
|
| Identifiers | |
| |
| CAS Number | Page Template:Plainlist/styles.css has no content. |
| PubChem CID | Page Template:Plainlist/styles.css has no content. |
| PubChem SID | Page Template:Plainlist/styles.css has no content. |
| IUPHAR/BPS | Page Template:Plainlist/styles.css has no content. |
| DrugBank | Page Template:Plainlist/styles.css has no content. |
| ChemSpider | Page Template:Plainlist/styles.css has no content. |
| UNII | Page Template:Plainlist/styles.css has no content. |
| KEGG | Page Template:Plainlist/styles.css has no content. |
| ChEBI | Page Template:Plainlist/styles.css has no content. |
| ChEMBL | Page Template:Plainlist/styles.css has no content. |
| NIAID ChemDB | Page Template:Plainlist/styles.css has no content. |
| PDB ligand | Page Template:Plainlist/styles.css has no content. |
| CompTox Dashboard (EPA) | Page Template:Plainlist/styles.css has no content. |
| Chemical and physical data | |
| Formula | C13H11F6N3O5 |
| Molar mass | 403.237 g·mol−1 |
| 3D model (JSmol) | Page Template:Plainlist/styles.css has no content. |
| |
| |
| Data page | |
| Template:Infobox drug/data page link | |
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 belongs to a class of molecules known as perfluoroacylamido-arylpropanamides.[6]
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] The patent for Topilutamide expired in 2020.[6]
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] Topilutamide is approved for cosmetic use in Europe but has not received FDA approval nor approval by the EMA for the treatment of androgenetic alopecia.[8] Finasteride and Minoxidil are currently the only treatments approved for the treatment of this condition.[2]
Available forms
Under the brand name 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] Fluridil binds to the androgen receptor with approximately a 9-15-fold higher affinity than more primitive NSAAs such as bicalutamide and hydroxyflutamide, but more research is required to validate these findings.[6]
| Compound | 3 μM | 10 μM |
|---|---|---|
| BP-766 (Topilutamide) | 41 ± 5 | 95.9 ± 6 |
| BP-521 | 62 ± 7 | 100 |
| BP-34 | 3 ± 4 | 2 ± 2 |
| Bicalutamide | 3 ± 3 | 11 ± 3 |
| Hydroxyflutamide | 2 ± 6 | 6 ± 7 |
Pharmacokinetics
Topilutamide is a topical medication and is applied to the scalp.[1][2][3][4][5] Topilutamide degrades in human serum at 37 °C with a half-life of approximately 6 hours and is undetectable after 48 hours.[6] Perfluoroacylamido-arylpropanamides decompose hydrolytically to BP-34 and their corresponding perfluorocarboxylic acid.[6] In the case of topilutamide, that perfluorocarboxylic acid is trifluoroacetic acid.[6] The two metabolites of topilutamide namely BP-34 and trifluoroacetic acid were undetectable in human serum (below the detection limit of 5 ng/mL) along with the parent compound topilutamide, in human studies.[6] BP-34 was shown to be devoid of anti-androgenic activity.[6]
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 INN.[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
Page Template:Reflist/styles.css has no content.
- ^ a b c d e f g Page Module:Citation/CS1/styles.css has no content.Sovak M, Seligson AL, Kucerova R, Bienova M, Hajduch M, Bucek M (August 2002). "Fluridil, a rationally designed topical agent for androgenetic alopecia: first clinical experience". Dermatologic Surgery. 28 (8): 678–85. doi:10.1046/j.1524-4725.2002.02017.x. PMID 12174057. S2CID 36439600.
- ^ a b c d e f g h Page Module:Citation/CS1/styles.css has no content.Haber RS, Stough DB (2006). Hair Transplantation. Elsevier Health Sciences. pp. 7–. ISBN 1-4160-3104-9.
- ^ a b c d e f g h Page Module:Citation/CS1/styles.css has no content.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).
- ^ a b c d e f g h Page Module:Citation/CS1/styles.css has no content.Avram MR, Rogers NE (30 November 2009). Hair Transplantation. Cambridge University Press. pp. 11–. ISBN 978-1-139-48339-1.
- ^ a b c d e f g Page Module:Citation/CS1/styles.css has no content.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.
- ^ a b c d e f g h i j k l Page Module:Citation/CS1/styles.css has no content.Seligson AL, Campion BK, Brown JW, Terry RC, Kucerova R, Bienova M, Hajduch M, Sovak M (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.
- ^ a b c d Page Module:Citation/CS1/styles.css has no content.Hermkens PH, Kamp S, Lusher S, Veeneman GH (July 2006). "Non-steroidal steroid receptor modulators". IDrugs. 9 (7): 488–94. doi:10.2174/0929867053764671. PMID 16821162.
- ^ a b c Page Module:Citation/CS1/styles.css has no content."Androgenetic Alopecia, Hair loss, Eucapil". www.eucapil.com.
- ^ Page Module:Citation/CS1/styles.css has no content.Chambers M. "ChemIDplus - 260980-89-0 - YCNCRLKXSLARFT-UHFFFAOYSA-N - Topilutamide [INN] - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
- ^ Page Module:Citation/CS1/styles.css has no content."Microsoft Word - final_PL91.doc" (PDF). Retrieved 2018-10-04.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found. Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found. Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found.
