Befloxatone

• CAT Number: M107567
• CAS Number: 134564-82-2
• Molecular Formula: C15H18F3NO5
• Molecular Weight: 349.306
• Purity: ≥95%
• Target: Monoamine Oxidase
• Storage: Desiccate at -20C
• IUPAC Name: (5R)-5-(methoxymethyl)-3-[4-[(3R)-4,4,4-trifluoro-3-hydroxybutoxy]phenyl]-1,3-oxazolidin-2-one
• InChI: InChI=1S/C15H18F3NO5/c1-22-9-12-8-19(14(21)24-12)10-2-4-11(5-3-10)23-7-6-13(20)15(16,17)18/h2-5,12-13,20H,6-9H2,1H3/t12-,13-/m1/s1
• InChIKey: IALVDLPLCLFBCF-CHWSQXEVSA-N
• SMILES: COCC1CN(C(=O)O1)C2=CC=C(C=C2)OCCC(C(F)(F)F)O

Befloxatone, also known as MD-370503, is a potent, selective and reversible inhibitor of monoamine oxidase A. Befloxatone inhibited selectively and competitively monoamine oxidase (MAO)-A in human and rat brain, heart, liver and duodenum homogenates with Ki values ranging from 1.9 to 3.6 nM for MAO-A and from 270 to 900 nM for MAO-B. In vitro, befloxatone was more potent at inhibiting MAO-A activity than reference compounds (befloxatone > harmaline > brofaromine > BW 137OU87 > RS 8359 > toloxatone > moclobemide).

Reference

1:[11C]befloxatone distribution is well correlated to monoamine oxidase A protein levels in the human brain. Zanotti-Fregonara P, Bottlaender M.J Cereb Blood Flow Metab. 2014 Dec;34(12):1951-2. doi: 10.1038/jcbfm.2014.157. Epub 2014 Sep 17. PMID: 25227605 Free PMC Article2:Imaging of monoamine oxidase-A in the human brain with [11C]befloxatone: quantification strategies and correlation with mRNA transcription maps. Zanotti-Fregonara P, Leroy C, Rizzo G, Roumenov D, Trichard C, Martinot JL, Bottlaender M.Nucl Med Commun. 2014 Dec;35(12):1254-61. doi: 10.1097/MNM.0000000000000196. PMID: 25185897 3:Kinetic analysis of [11C]befloxatone in the human brain, a selective radioligand to image monoamine oxidase A. Zanotti-Fregonara P, Leroy C, Roumenov D, Trichard C, Martinot JL, Bottlaender M.EJNMMI Res. 2013 Nov 25;3(1):78. doi: 10.1186/2191-219X-3-78. PMID: 24274579 Free PMC Article4:[¹¹C]befloxatone brain kinetics is not influenced by Bcrp function at the blood-brain barrier: a PET study using Bcrp TGEM knockout rats. Hosten B, Boisgard R, Jacob A, Goutal S, Saubaméa B, Dollé F, Scherrmann JM, Cisternino S, Tournier N.Eur J Pharm Sci. 2013 Nov 20;50(3-4):520-5. doi: 10.1016/j.ejps.2013.08.015. Epub 2013 Aug 24. PMID: 23981334 5:In vivo quantification of monoamine oxidase A in baboon brain: a PET study using [(11)C]befloxatone and the multi-injection approach. Bottlaender M, Valette H, Delforge J, Saba W, Guenther I, Curet O, George P, Dollé F, Grégoire MC.J Cereb Blood Flow Metab. 2010 Apr;30(4):792-800. doi: 10.1038/jcbfm.2009.242. Epub 2009 Nov 18. PMID: 19920845 Free PMC Article6:Cerebral monoamine oxidase A inhibition in tobacco smokers confirmed with PET and [11C]befloxatone. Leroy C, Bragulat V, Berlin I, Grégoire MC, Bottlaender M, Roumenov D, Dollé F, Bourgeois S, Penttilä J, Artiges E, Martinot JL, Trichard C.J Clin Psychopharmacol. 2009 Feb;29(1):86-8. doi: 10.1097/JCP.0b013e31819e98f. PMID: 19142115 7:Befloxatone (Synthelabo). Emilien G.IDrugs. 1999 Mar;2(3):247-53. PMID: 16160936 8:Acute inhibition of cardiac monoamine oxidase A after tobacco smoke inhalation: validation study of [11C]befloxatone in rats followed by a positron emission tomography application in baboons. Valette H, Bottlaender M, Dollé F, Coulon C, Ottaviani M, Syrota A.J Pharmacol Exp Ther. 2005 Jul;314(1):431-6. Epub 2005 Apr 15. PMID: 15833896 Free Article9:Synthesis and in vivo imaging properties of [11C]befloxatone: a novel highly potent positron emission tomography ligand for mono-amine oxidase-A. Dolle F, Valette H, Bramoulle Y, Guenther I, Fuseau C, Coulon C, Lartizien C, Jegham S, George P, Curet O, Pinquier JL, Bottlaender M.Bioorg Med Chem Lett. 2003 May 19;13(10):1771-5. PMID: 12729662 10:Mapping the cerebral monoamine oxidase type A: positron emission tomography characterization of the reversible selective inhibitor [11C]befloxatone. Bottlaender M, Dolle F, Guenther I, Roumenov D, Fuseau C, Bramoulle Y, Curet O, Jegham J, Pinquier JL, George P, Valette H.J Pharmacol Exp Ther. 2003 May;305(2):467-73. Epub 2003 Feb 11. PMID: 12606609 Free Article