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Merck
CN

SML4054

Sigma-Aldrich

AFQ056

≥98% (HPLC)

Synonym(s):

(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester, AFQ 056, Mavoglurant

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About This Item

Empirical Formula (Hill Notation):
C19H23NO3
CAS Number:
543906-09-8
Molecular Weight:
313.39
MDL number:
MFCD30534423
UNSPSC Code:
12352200

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

O[C@]1(C#CC2=CC(C)=CC=C2)[C@@]3([H])[C@@](N(C(OC)=O)CC3)([H])CCC1

InChI key

ZFPZEYHRWGMJCV-ZHALLVOQSA-N

Biochem/physiol Actions

Orally active, potent and selective mGluR5 antagonist.

AFQ056 (Mavoglurant) is an orally active, potent and selective antagonist of metabotropic glutamate receptor 5 (mGluR5). AFQ056 was investigated for treatment of fragile X syndrome and for Parkinson′s disease.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000374997
0000374998
0000362350
0000374998
0000374997

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Sébastien Jacquemont et al.
Science translational medicine, 3(64), 64ra1-64ra1 (2011-01-07)
Fragile X syndrome (FXS) is an X-linked condition associated with intellectual disability and behavioral problems. It is caused by expansion of a CGG repeat in the 5' untranslated region of the fragile X mental retardation 1 (FMR1) gene. This mutation
Laurent Grégoire et al.
Parkinsonism & related disorders, 17(4), 270-276 (2011-02-15)
Overactivity of glutamatergic transmission has been implicated in Parkinson's disease (PD) and levodopa (L-Dopa)-induced dyskinesias. Striatal metabotropic glutamate receptors type 5 (mGluR5) are abundant and provide specific targets to modulate glutamatergic activity. This study investigated the acute effects of the
Kirstie A Bennett et al.
The Journal of pharmacology and experimental therapeutics, 377(1), 157-168 (2021-02-06)
The metabotropic glutamate receptor 5 (mGlu5) is a recognized central nervous system therapeutic target for which several negative allosteric modulator (NAM) drug candidates have or are continuing to be investigated for various disease indications in clinical development. Direct measurement of

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