Befiradol

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Befiradol
F-13640 structure.png
Systematic (IUPAC) name
3-chloro-4-fluorophenyl-[4-fluoro-4-([(5-methylpyridin-2-yl)methylamino]methyl)piperidin-1-yl]methanone
Clinical data
Legal status
  • Uncontrolled
Identifiers
CAS Number 208110-64-9 N
ATC code none
PubChem CID: 9865384
IUPHAR/BPS 3925
ChemSpider 8041076 YesY
UNII RAT9OHA1YH YesY
ChEMBL CHEMBL45305 YesY
Chemical data
Formula C20H22ClF2N3O
Molecular mass 393.857 g/mol
  • n2cc(C)ccc2CNCC(F)(CC3)CCN3C(=O)c(cc1Cl)ccc1F
  • InChI=1S/C20H22ClF2N3O/c1-14-2-4-16(25-11-14)12-24-13-20(23)6-8-26(9-7-20)19(27)15-3-5-18(22)17(21)10-15/h2-5,10-11,24H,6-9,12-13H2,1H3 YesY
  • Key:PKZXLMVXBZICTF-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Befiradol (F-13,640; NLX-112) is a very potent and highly selective 5-HT1A receptor full agonist. It has powerful analgesic and antiallodynic effects comparable to those of high doses of opioid painkillers, but with fewer and less prominent side effects, as well as little or no development of tolerance with repeated use.[1][2][3][4][5][6] A SAR study revealed that replacement of the dihalophenyl moiety by 3-benzothienyl increases maximal efficacy from 84% to 124% (Ki=2.7 nM).[7]

Befiradol was discovered and developed by Pierre Fabre Médicament, a French pharmaceuticals company. In September 2013, befiradol was out-licensed to Neurolixis, a California-based biotechnology company. Neurolixis announced that it intends to re-purpose befiradol for the treatment of Levodopa-induced dyskinesia in Parkinson's disease.[8] In support of this indication, preclinical data was published describing the activity of befiradol in animal models of Parkinson's disease.[9][10]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Bernard Vacher, Bernard Bonnaud, Wouter Koek. Pyridin-2-yl-methylamine derivatives, method of preparing and application as medicine. US Patent 6020345, May 21, 1999.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ http://neurolixis.com/images/stories/nlx_pf_license_23sept13.pdf
  9. ↑ NLX-112, a novel 5-HT1A receptor agonist for the treatment of L-DOPA-induced dyskinesia: Behavioral and neurochemical profile in rat. Iderberg H, McCreary AC, Varney MA, Kleven MS, Koek W, Bardin L, Depoortère R, Cenci MA, Newman-Tancredi A. Exp Neurol. 2015 Sep;271:335-50. doi: 10.1016/j.expneurol.2015.05.021. Epub 2015 May 30. PMID: 26037043
  10. ↑ The novel 5-HT1A receptor agonist, NLX-112 reduces l-DOPA-induced abnormal involuntary movements in rat: A chronic administration study with microdialysis measurements. McCreary AC, Varney MA, Newman-Tancredi A. Neuropharmacology. 2016 Jan 9;105:651-660. doi: 10.1016/j.neuropharm.2016.01.013. PMID: 26777281
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