Safinamide

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Safinamide
Safinamide.svg
Systematic (IUPAC) name
N2-{4-[(3-fluorobenzyl)oxy]benzyl}-L-alaninamide
Clinical data
Legal status
  • UK: Authorised
Identifiers
CAS Number 133865-89-1 N
Template:CAS (mesylate)
ATC code none
PubChem CID: 131682
ChemSpider 116349 YesY
UNII 90ENL74SIG YesY
KEGG D10158 N
ChEMBL CHEMBL396778 YesY
Synonyms (2S)-2-[[4-[(3-Fluorophenyl)methoxy]phenyl] methylamino]propanamide
Chemical data
Formula C17H19FN2O2
Molecular mass 302.34 g/mol
  • O=C(N)[C@@H](NCc2ccc(OCc1cccc(F)c1)cc2)C
  • InChI=1S/C17H19FN2O2/c1-12(17(19)21)20-10-13-5-7-16(8-6-13)22-11-14-3-2-4-15(18)9-14/h2-9,12,20H,10-11H2,1H3,(H2,19,21)/t12-/m0/s1 YesY
  • Key:NEMGRZFTLSKBAP-LBPRGKRZSA-N YesY
 NYesY (what is this?)  (verify)

Safinamide (INN; brand name Xadago, former developmental code name EMD-1195686) is a drug indicated for the treatment of Parkinson's disease with multiple methods of action.[1] In 2007, a Phase III clinical trial was started. It was scheduled to run until 2011.[2] The compound was originally discovered at Farmitalia-Carlo Erba, first published in 1998[3] and developed by Newron Pharmaceuticals, which sold the rights to Merck-Serono in 2006. In October 2011 Merck-Serono announced that they would give all rights to develop the compound back to Newron.[4]

Potential additional uses might be restless legs syndrome (RLS) and epilepsy.[5] They were being tested in Phase II trials in 2008, but no results are available.

Adverse effects

Common adverse events in clinical trials were nausea, dizziness, tiredness, headache and backache. There was no significant difference in the occurrence of these effects between safinamide and placebo treated patients.[6]

Methods of action

Parkinson and RLS relevant mechanisms

Safinamide is a reversible and selective monoamine oxidase B inhibitor, reducing degradation of dopamine, and a glutamate release inhibitor.[6][7] It also inhibits dopamine reuptake.[8] Additionally, safinamide blocks sodium and calcium channels.[7][9] Safinamide has been approved by the European Medicines Agency for the treatment of adult patients with idiopathic Parkinson’s disease as add-on therapy to a stable dose of Levodopa (L-dopa) alone or in combination with other PD drugs in patients with mid-to-late-stage fluctuating disease.[10]

See also

  • Ralfinamide, very similar structure (different fluorine position)
  • Evenamide, structurally-related antipsychotic in-development
  • Lacosamide, used for partial-onset seizures and diabetic neuropathic pain
  • Ziconotide, a peptide analgesic

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Study of Safinamide in Early Parkinson's Disease as Add-on to Dopamine Agonist (MOTION)
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Merck Returns Rights for Safinamide to Newron, 21 October 2011.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Merck Serono: Vielversprechende Daten zur kognitiven Wirkung von Safinamid bei Parkinson im Frühstadium. (German) 8 June 2007.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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