Mavoglurant

Mavoglurant
Names
Preferred IUPAC name
Methyl (3aR,4S,7aR)-4-hydroxy-4-[(3-methylphenyl)ethynyl]octahydro-1H-indole-1-carboxylate
Other names
AFQ056
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.219.728
Edit this at Wikidata
PubChem CID
UNII
InChI
  • InChI=1S/C19H23NO3/c1-14-5-3-6-15(13-14)8-11-19(22)10-4-7-17-16(19)9-12-20(17)18(21)23-2/h3,5-6,13,16-17,22H,4,7,9-10,12H2,1-2H3/t16-,17-,19-/m1/s1
    Key: ZFPZEYHRWGMJCV-ZHALLVOQSA-N
  • InChI=1/C19H23NO3/c1-14-5-3-6-15(13-14)8-11-19(22)10-4-7-17-16(19)9-12-20(17)18(21)23-2/h3,5-6,13,16-17,22H,4,7,9-10,12H2,1-2H3/t16-,17-,19-/m1/s1
    Key: ZFPZEYHRWGMJCV-ZHALLVOQBN
SMILES
  • O=C(OC)N3[C@@H]2CCC[C@@](O)(C#Cc1cccc(c1)C)[C@@H]2CC3
Properties
Chemical formula
C19H23NO3
Molar mass 313.397 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mavoglurant (developmental code name AFQ-056) is an experimental drug candidate for the treatment of fragile X syndrome and other conditions which has been discontinued.[1][2] It exerts its effect as an antagonist of the metabotropic glutamate receptor 5 (mGluR5).[3]

Mavoglurant was under development by Novartis and reached phase II and phase III clinical trials.[2][4] Phase IIb/III dose finding and evaluation trials for fragile X-syndrome were discontinued by the end of 2014.[5] Otherwise, it would have been the first drug to treat the underlying disorder instead of the symptoms of fragile X syndrome.[6] Mavoglurant was also in phase II clinical trials for Levodopa-induced dyskinesia.[7][8] In 2007, Norvartis had conducted a clinical study to assess its ability of reducing cigarette smoking, but no results had been published up till now.[9] Novartis was conducting a clinical trial with this drug on obsessive–compulsive disorder.[10]

Novartis discontinued development of mavoglurant for fragile X syndrome in April 2014 following disappointing trial results.[11] Development was discontinued for other indications by 2017.[1]

See also

References

  1. 1 2 "Mavoglurant - AdisInsight".
  2. 1 2 P. Cole (2012). "Mavoglurant". Drugs of the Future. 37 (1): 7–12. doi:10.1358/dof.2012.037.01.1772147.
  3. Levenga, J; Hayashi, S; De Vrij, FM; Koekkoek, SK; Van Der Linde, HC; Nieuwenhuizen, I; Song, C; Buijsen, RA; et al. (2011). "AFQ056, a new mGluR5 antagonist for treatment of fragile X syndrome". Neurobiology of Disease. 42 (3): 311–7. doi:10.1016/j.nbd.2011.01.022. PMID 21316452. S2CID 45389434.
  4. Jacquemont, S.; Curie, A.; Des Portes, V.; Torrioli, M. G.; Berry-Kravis, E.; Hagerman, R. J.; Ramos, F. J.; Cornish, K.; et al. (2011). "Epigenetic Modification of the FMR1 Gene in Fragile X Syndrome is Associated with Differential Response to the mGluR5 Antagonist AFQ056". Science Translational Medicine. 3 (64): 64ra1. doi:10.1126/scitranslmed.3001708. PMID 21209411. S2CID 206677267.
  5. "Novartis Discontinues Development of mavoglurant (AFQ056) for Fragile X Syndrome • Fragile X Research - FRAXA Research Foundation". 2014-04-24.
  6. "AFQ056 drug improves symptoms in Fragile X patients: Study". news-medical.net. January 9, 2011.
  7. Kumar, R; Hauser, R. A.; Mostillo, J; Dronamraju, N; Graf, A; Merschhemke, M; Kenney, C (Sep 2013). "Mavoglurant (AFQ056) in combination with increased levodopa dosages in Parkinson's disease patients". Int J Neurosci. 126 (1): 20–4. doi:10.3109/00207454.2013.841685. PMID 24007304. S2CID 7531940.
  8. "NHI Clinical trials".
  9. "Effects of AFQ056 and Nicotine in Reducing Cigarette Smoking".
  10. "Study to Evaluate the Effect of AFQ056 in Obsessive Compulsive Disorder (OCD)".
  11. FRAXA (2014). "Novartis Discontinues Development of mavoglurant (AFQ056) for Fragile X Syndrome".



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