Compound: Mavoglurant
SMILES: O=C(OC)N1[C@H]2[C@H]([C@](O)(C#Cc3cc(ccc3)C)CCC2)CC1
InChIKey: ZFPZEYHRWGMJCV-ZHALLVOQSA-N
Synonyms: Mavoglurant, 543906-09-8, AFQ056, AFQ-056, GT0I9SV4F6, DTXSID30202777, 1H-Indole-1-carboxylic acid, octahydro-4-hydroxy-4-(2-(3-methylphenyl)ethynyl)-, methyl ester, (3aR,4S,7aR)-, methyl (3aR,4S,7aR)-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate, mavoglurantum, methyl (3aR,4S,7aR)-4-hydroxy-4-(2-(3-methylphenyl)ethynyl)-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate, RefChem:155994, DTXCID60125268, methyl (3aR,4S,7aR)-4-hydroxy-4-(2-(3-methylphenyl)ethynyl)-octahydro-1H-indole-1-carboxylate, Mavoglurant racemate, 1636881-61-2, (3ar,4s,7ar)-octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1h-indole-1-carboxylic acid methyl ester, (3aR,4S,7aR)-Methyl 4-hydroxy-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate, methyl (3aR,4S,7aR)-4-hydroxy-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate, (-)-(3aR,4S,7aR)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester, Methyl (3ar,4s,7ar)-4-Hydroxy-4-[(3-Methylphenyl)ethynyl]octahydro-1h-Indole-1-Carboxylate, Mavoglurant [INN], Mavoglurant [USAN:INN], UNII-GT0I9SV4F6, AFQ 056, MFCD18633263, 4oo9, Mavoglurant, AFQ056, MAVOGLURANT [USAN], Mavoglurant (AFQ 056)?, MAVOGLURANT [WHO-DD], orb198441, SCHEMBL989279, GTPL7586, orb1709192, orb3132236, CHEMBL3087515, SCHEMBL29744485, ZFPZEYHRWGMJCV-ZHALLVOQSA-N, GLXC-15608, EX-A1564, BDBM50443085, AKOS027326541, CS-5245, DB13004, AS-79009, HY-15257, DB-102250, NS00069300, F85319, F85489, Q6589598, BRD-K07790550-001-01-6, (3aR,4S,7aR)-Octahydro-4-hydroxy-4-[(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic Acid Methyl Ester; AFQ 056, 1H-INDOLE-1-CARBOXYLIC ACID, OCTAHYDRO-4-HYDROXY-4-((3-METHYLPHENYL)ETHYNYL)-, METHYL ESTER, (3AR,4S,7AR)-, 2U8, Methyl (3aR,4S,7aR)-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]octahydro-1H-indole-1-carboxylate, methyl (3aR,4S,7aR)-4-hydroxy-4-[2-(m-tolyl)ethynyl]-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate
Theoretical properties:
molecular_formula: C19H23NO3
molecular_weight: 313.4 g/mol
exact_mass: 313.16779360 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 23
topological_polar_surface_area: 49.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: MAVOGLURANT is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Mavoglurant (developmental code name AFQ-056) is an experimental drug candidate for the treatment of fragile X syndrome and other conditions.  It exerts its effect as an antagonist of the metabotropic glutamate receptor 5 (mGluR5).
Mavoglurant was under development by Novartis and reached phase II and phase III clinical trials. Phase IIb/III dose finding and evaluation trials for fragile X-syndrome were discontinued by the end of 2014. Otherwise, it would have been the first drug to treat the underlying disorder instead of the symptoms of fragile X syndrome. Mavoglurant was also in phase II clinical trials for Levodopa-induced dyskinesia. 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. Novartis was conducting a clinical trial with this drug on obsessive–compulsive disorder.
Novartis discontinued development of mavoglurant for fragile X syndrome in April 2014 following disappointing trial results. Development was discontinued for other indications by 2017.
Recently, Stalicla, a biotech company applying artificial intelligence to identify subgroups of high-responder patients, acquired worldwide rights from Novartis to progress the drug for substance-use and neurodevelopmental disorders.