Safinamide
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| Systematic (IUPAC) name | |
|---|---|
|
N2-{4-[(3-fluorobenzyl)oxy]benzyl}-L-alaninamide | |
| Legal status | |
| Legal status |
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| Identifiers | |
| CAS Number |
133865-89-1  202825-46-5 (mesylate) |
| ATC code | none |
| PubChem | CID 131682 |
| ChemSpider |
116349  |
| UNII |
90ENL74SIG |
| KEGG |
D10158 |
| ChEMBL |
CHEMBL396778 |
| Synonyms | (2S)-2-[[4-[(3-Fluorophenyl)methoxy]phenyl] methylamino]propanamide |
| Chemical data | |
| Formula | C17H19FN2O2 |
| Molar mass | 302.34 g/mol |
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| (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
- ↑ Fariello, RG (2007). "Safinamide". Neurotherapeutics 4 (1): 110–116. doi:10.1016/j.nurt.2006.11.011. PMID 17199024.
- ↑ Study of Safinamide in Early Parkinson's Disease as Add-on to Dopamine Agonist (MOTION)
- ↑ Pevarello, P; Bonsignori, A; Dostert, P; Heidempergher, F; Pinciroli, V; Colombo, M; McArthur, RA; Varasi, M (1998). "Synthesis and Anticonvulsant Activity of a New Class of 2-[(Arylalkyl)amino]alkanamide Derivatives". Journal of Medicinal Chemistry 41 (4): 579–590. doi:10.1021/jm970599m. PMID 9484507.
- ↑ Merck Returns Rights for Safinamide to Newron, 21 October 2011.
- ↑ Chazot, PL (2007). "Drug evaluation: Safinamide for the treatment of Parkinson's disease, epilepsy and restless legs syndrome". Current Opinion in Investigational Drugs 8 (7): 570–579. PMID 17659477.
- 1 2 H. Spreitzer (14 April 2014). "Neue Wirkstoffe – Safinamid". Österreichische Apothekerzeitung (in German) (8/2014): 30.
- 1 2 Caccia, C; Maj, R; Calabresi, M; Maestroni, S; Faravelli, L; Curatolo, L; Salvati, P; Fariello, RG (2006). "Safinamide: From molecular targets to a new anti-Parkinson drug". Neurology 67 (7 Suppl 2): S18–23. doi:10.1212/wnl.67.7_suppl_2.s18. PMID 17030736.
- ↑ Merck Serono: Vielversprechende Daten zur kognitiven Wirkung von Safinamid bei Parkinson im Frühstadium. (German) 8 June 2007.
- ↑ Pevarello, P; Bonsignori, A; Caccia, C; Amici, R; Salvati, P; Fariello, RG; McArthur, RA; Varasi, M (1999). "Sodium channel activity and sigma binding of 2-aminopropanamide anticonvulsants". Bioorganic & Medicinal Chemistry Letters 9 (17): 2521–2524. doi:10.1016/s0960-894x(99)00415-1.
- ↑ Lawrence, Janna (2015-01-19). "Safinamide recommended for approval as Parkinson’s disease therapy". The Pharmaceutical Journal (Royal Pharmaceutical Society). Retrieved 2015-01-19.
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