Ralfinamide

Ralfinamide (INN) (code names NW-1029, FCE-26742A, PNU-0154339E)[1] is a multimodal drug which is under investigation by Newron Pharmaceuticals for the treatment of neuropathic pain and other pain conditions such as post-operative dental pain.[2][3][4][5]

Not to be confused with Rufinamide.

Ralfinamide

Clinical data
ATC code	None
Identifiers
IUPAC name N^2-{4-[(2-Fluorobenzyl)oxy]benzyl}-L-alaninamide
CAS Number	133865-88-0
PubChem CID	5745207
ChemSpider	4676525
UNII	3LPF0S0GVV
ChEMBL	ChEMBL2107771
CompTox Dashboard (EPA)	DTXSID70158406
ECHA InfoCard	100.120.272
Chemical and physical data
Formula	C17H19FN2O2
Molar mass	302.349 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@@H](C(=O)N)NCc1ccc(cc1)OCc2ccccc2F
InChI InChI=1S/C17H19FN2O2/c1-12(17(19)21)20-10-13-6-8-15(9-7-13)22-11-14-4-2-3-5-16(14)18/h2-9,12,20H,10-11H2,1H3,(H2,19,21)/t12-/m0/s1 Key:BHJIBOFHEFDSAU-LBPRGKRZSA-N

It has a relatively complex pharmacology, acting as a mixed voltage-gated sodium channel blocker (including Na_v1.7),[2][3] N-type calcium channel blocker,[2][3] noncompetitive NMDA receptor antagonist,[6] and monoamine oxidase B inhibitor.[7][8]

It has thus far progressed as far as phase IIb/phase III clinical trials.[5][9] In 2010 it failed a phase II trial for lower back pain.[10] Encouraging Phase II results have been announced for neuropathic pain.[11]

See also

• List of investigational analgesics
• Safinamide, different fluorine position
• Evenamide, structurally-related antipsychotic in development
• Lacosamide, used for partial-onset seizures and diabetic neuropathic pain
• Ziconotide, FDA approved peptide for chronic neuropathic pain

References

1. Pain: New Insights for the Healthcare Professional: 2013 Edition. ScholarlyEditions. 22 July 2013. pp. 506–. ISBN 978-1-4816-6118-8.
2. David M. Simpson; Justin C. McArthur; Robert H. Dworkin (21 June 2012). Neuropathic Pain: Mechanisms, Diagnosis and Treatment. Oxford University Press. pp. 40–. ISBN 978-0-19-539470-2.
3. Raymond S. Sinatra; Jonathan S. Jahr; J. Michael Watkins-Pitchford (14 October 2010). The Essence of Analgesia and Analgesics. Cambridge University Press. pp. 436–. ISBN 978-1-139-49198-3.
4. Annual Reports in Medicinal Chemistry. Academic Press. 17 December 2008. pp. 55–. ISBN 978-0-08-092187-7.
5. Chuang Lu; Albert P. Li (26 January 2010). Enzyme Inhibition in Drug Discovery and Development: The Good and the Bad. John Wiley & Sons. pp. 689–. ISBN 978-0-470-53894-4.
6. Colombo, E.; Curatolo, L.; Caccia, C.; Salvati, P.; Faravelli, L. (2007). "344 Ralfinamide Acts Through Nmda Receptor Complex: A Central Role for Chronic Pain Treatment". European Journal of Pain. 11 (S1): S152–S153. doi:10.1016/j.ejpain.2007.03.359. ISSN 1090-3801.
7. Di Stefano AF, Radicioni MM, Rusca A (May 2013). "Pressor response to oral tyramine and monoamine oxidase inhibition during treatment with ralfinamide (NW-1029)". Neurotox Res. 23 (4): 315–26. doi:10.1007/s12640-012-9344-5. PMID 22872464.
8. Humphrey P. Rang; Maureen M. Dale; James M. Ritter; Rod J. Flower; Graeme Henderson (14 April 2011). Rang & Dale's Pharmacology: with STUDENT CONSULT Online Access. Elsevier Health Sciences. pp. 2476–. ISBN 978-0-7020-4504-2.
9. Valentin K. Gribkoff; Leonard K. Kaczmarek (9 December 2008). Structure, Function and Modulation of Neuronal Voltage-Gated Ion Channels. John Wiley & Sons. pp. 377–. ISBN 978-0-470-42989-1.
10. Newron reports SERENA trial top-line results for ralfinamide
11. Newron Announces Positive Results With Ralfinamide From Phase II Trial in Neuropathic Pain

External links

• Ralfinamide - Newron Pharmaceuticals