Ralfinamide

Ralfinamide
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • N2-{4-[(2-Fluorobenzyl)oxy]benzyl}-L-alaninamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.120.272
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Chemical and physical data
FormulaC17H19FN2O2
Molar mass302.349 g·mol−1
3D model (JSmol)
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

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]

It has a relatively complex pharmacology, acting as a mixed voltage-gated sodium channel blocker (including Nav1.7),[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

References

  1. ↑ Pain: New Insights for the Healthcare Professional: 2013 Edition. ScholarlyEditions. 22 July 2013. pp. 506–. ISBN 978-1-4816-6118-8.
  2. 1 2 3 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. 1 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. 1 2 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. S2CID 58186567.
  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. S2CID 207442119.
  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


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