Mavoglurant
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MedKoo CAT#: 319677

CAS#: 543906-09-8

Description: Mavoglurant, aslo known as AFQ056, is an experimental drug candidate for the treatment of fragile X syndrome. Mavoglurant exerts its effect as an antagonist of the metabotropic glutamate receptor 5 (mGLU5). Novartis discontinued development of mavoglurant for fragile X syndrome in April 2014 following disappointing trial results. Currently Novartis is conducting a clinical trial with this drug on obsessive compulsive disorder.


Price and Availability

Size
Price

100mg
USD 1650
Size
Price

200mg
USD 2650
Size
Price

500mg
USD 3950

Mavoglurant, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319677
Name: Mavoglurant
CAS#: 543906-09-8
Chemical Formula: C19H23NO3
Exact Mass: 313.1678
Molecular Weight: 313.397
Elemental Analysis: C, 72.82; H, 7.40; N, 4.47; O, 15.32


Synonym: AFQ056; AFQ-056; AFQ 056; Mavoglurant.

IUPAC/Chemical Name: methyl (3aR,4S,7aR)-4-hydroxy-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate

InChi Key: ZFPZEYHRWGMJCV-ZHALLVOQSA-N

InChi Code: 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

SMILES Code: O=C(N1CC[C@@]2([H])[C@@](C#CC3=CC=CC(C)=C3)(O)CCC[C@@]12[H])OC


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Berry-Kravis E, Des Portes V, Hagerman R, Jacquemont S, Charles P, Visootsak J, Brinkman M, Rerat K, Koumaras B, Zhu L, Barth GM, Jaecklin T, Apostol G, von Raison F. Mavoglurant in fragile X syndrome: Results of two randomized, double-blind, placebo-controlled trials. Sci Transl Med. 2016 Jan 13;8(321):321ra5. doi: 10.1126/scitranslmed.aab4109. PubMed PMID: 26764156.

2: Wendling T, Dumitras S, Ogungbenro K, Aarons L. Application of a Bayesian approach to physiological modelling of mavoglurant population pharmacokinetics. J Pharmacokinet Pharmacodyn. 2015 Dec;42(6):639-57. doi: 10.1007/s10928-015-9430-4. Epub 2015 Aug 1. PubMed PMID: 26231433.

3: Sivasubramanian R, Chakraborty A, Rouzade-Dominguez ML, Neelakantham S, Jakab A, Mensinga T, Legangneux E, Woessner R, Ufer M. Effect of mavoglurant (AFQ056), a selective mGluR5 antagonist, on the pharmacokinetics of a combined oral contraceptive containing ethinyl estradiol and levonorgestrel in healthy women. Int J Clin Pharmacol Ther. 2015 Jul;53(7):550-6. doi: 10.5414/CP202321. PubMed PMID: 25943176.

4: Wendling T, Ogungbenro K, Pigeolet E, Dumitras S, Woessner R, Aarons L. Model-based evaluation of the impact of formulation and food intake on the complex oral absorption of mavoglurant in healthy subjects. Pharm Res. 2015 May;32(5):1764-78. doi: 10.1007/s11095-014-1574-1. Epub 2014 Nov 26. PubMed PMID: 25425054.

5: Vranesic I, Ofner S, Flor PJ, Bilbe G, Bouhelal R, Enz A, Desrayaud S, McAllister K, Kuhn R, Gasparini F. AFQ056/mavoglurant, a novel clinically effective mGluR5 antagonist: identification, SAR and pharmacological characterization. Bioorg Med Chem. 2014 Nov 1;22(21):5790-803. doi: 10.1016/j.bmc.2014.09.033. Epub 2014 Sep 20. PubMed PMID: 25316499.

6: Petrov D, Pedros I, de Lemos ML, Pallàs M, Canudas AM, Lazarowski A, Beas-Zarate C, Auladell C, Folch J, Camins A. Mavoglurant as a treatment for Parkinson's disease. Expert Opin Investig Drugs. 2014 Aug;23(8):1165-79. doi: 10.1517/13543784.2014.931370. Epub 2014 Jun 24. Review. PubMed PMID: 24960254.

7: Gomez-Mancilla B, Berry-Kravis E, Hagerman R, von Raison F, Apostol G, Ufer M, Gasparini F, Jacquemont S. Development of mavoglurant and its potential for the treatment of fragile X syndrome. Expert Opin Investig Drugs. 2014 Jan;23(1):125-34. doi: 10.1517/13543784.2014.857400. Epub 2013 Nov 20. Review. PubMed PMID: 24251408.

8: Kumar R, Hauser RA, Mostillo J, Dronamraju N, Graf A, Merschhemke M, Kenney C. Mavoglurant (AFQ056) in combination with increased levodopa dosages in Parkinson's disease patients. Int J Neurosci. 2016 Jan;126(1):20-4. doi: 10.3109/00207454.2013.841685. Epub 2015 Aug 18. PubMed PMID: 24007304.

9: Walles M, Wolf T, Jin Y, Ritzau M, Leuthold LA, Krauser J, Gschwind HP, Carcache D, Kittelmann M, Ocwieja M, Ufer M, Woessner R, Chakraborty A, Swart P. Metabolism and disposition of the metabotropic glutamate receptor 5 antagonist (mGluR5) mavoglurant (AFQ056) in healthy subjects. Drug Metab Dispos. 2013 Sep;41(9):1626-41. doi: 10.1124/dmd.112.050716. Epub 2013 Jun 17. PubMed PMID: 23775850.

10: Pop AS, Levenga J, de Esch CE, Buijsen RA, Nieuwenhuizen IM, Li T, Isaacs A, Gasparini F, Oostra BA, Willemsen R. Rescue of dendritic spine phenotype in Fmr1 KO mice with the mGluR5 antagonist AFQ056/Mavoglurant. Psychopharmacology (Berl). 2014 Mar;231(6):1227-35. doi: 10.1007/s00213-012-2947-y. Epub 2012 Dec 21. PubMed PMID: 23254376.

11: Gantois I, Pop AS, de Esch CE, Buijsen RA, Pooters T, Gomez-Mancilla B, Gasparini F, Oostra BA, D'Hooge R, Willemsen R. Chronic administration of AFQ056/Mavoglurant restores social behaviour in Fmr1 knockout mice. Behav Brain Res. 2013 Feb 15;239:72-9. doi: 10.1016/j.bbr.2012.10.059. Epub 2012 Nov 6. PubMed PMID: 23142366.

12: Jakab A, Winter S, Raccuglia M, Picard F, Dumitras S, Woessner R, Mistry S, Chudasama J, Guttikar S, Kretz O. Validation of an LC-MS/MS method for the quantitative determination of mavoglurant (AFQ056) in human plasma. Anal Bioanal Chem. 2013 Jan;405(1):215-23. doi: 10.1007/s00216-012-6456-y. Epub 2012 Oct 13. PubMed PMID: 23064707.