Befloxatone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326886

CAS#: 134564-82-2

Description: 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).


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Befloxatone is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326886
Name: Befloxatone
CAS#: 134564-82-2
Chemical Formula: C15H18F3NO5
Exact Mass: 349.1137
Molecular Weight: 349.3062
Elemental Analysis: C, 51.58; H, 5.19; F, 16.32; N, 4.01; O, 22.90


Synonym: MD-370503; MD 370503; MD370503; MD-370,503; Befloxatone

IUPAC/Chemical Name: (R)-5-(Methoxymethyl)-3-(p-((R)-4,4,4-trifluoro-3-hydroxybutoxy)phenyl)-2-oxazolidinone

InChi Key: IALVDLPLCLFBCF-CHWSQXEVSA-N

InChi Code: 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

SMILES Code: O=C1O[C@@H](COC)CN1C2=CC=C(OCC[C@@H](O)C(F)(F)F)C=C2


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

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: Zanotti-Fregonara P, Bottlaender M. [11C]befloxatone distribution is well correlated to monoamine oxidase A protein levels in the human brain. J Cereb Blood Flow Metab. 2014 Dec;34(12):1951-2. doi: 10.1038/jcbfm.2014.157. Epub 2014 Sep 17. PubMed PMID: 25227605; PubMed Central PMCID: PMC4269741.

2: Zanotti-Fregonara P, Leroy C, Rizzo G, Roumenov D, Trichard C, Martinot JL, Bottlaender M. Imaging of monoamine oxidase-A in the human brain with [11C]befloxatone: quantification strategies and correlation with mRNA transcription maps. Nucl Med Commun. 2014 Dec;35(12):1254-61. doi: 10.1097/MNM.0000000000000196. PubMed PMID: 25185897.

3: Zanotti-Fregonara P, Leroy C, Roumenov D, Trichard C, Martinot JL, Bottlaender M. Kinetic analysis of [11C]befloxatone in the human brain, a selective radioligand to image monoamine oxidase A. EJNMMI Res. 2013 Nov 25;3(1):78. doi: 10.1186/2191-219X-3-78. PubMed PMID: 24274579; PubMed Central PMCID: PMC4176482.

4: Hosten B, Boisgard R, Jacob A, Goutal S, Saubaméa B, Dollé F, Scherrmann JM, Cisternino S, Tournier N. [¹¹C]befloxatone brain kinetics is not influenced by Bcrp function at the blood-brain barrier: a PET study using Bcrp TGEM knockout rats. Eur J Pharm Sci. 2013 Nov 20;50(3-4):520-5. doi: 10.1016/j.ejps.2013.08.015. Epub 2013 Aug 24. PubMed PMID: 23981334.

5: Bottlaender M, Valette H, Delforge J, Saba W, Guenther I, Curet O, George P, Dollé F, Grégoire MC. In vivo quantification of monoamine oxidase A in baboon brain: a PET study using [(11)C]befloxatone and the multi-injection approach. J Cereb Blood Flow Metab. 2010 Apr;30(4):792-800. doi: 10.1038/jcbfm.2009.242. Epub 2009 Nov 18. PubMed PMID: 19920845; PubMed Central PMCID: PMC2949159.

6: Leroy C, Bragulat V, Berlin I, Grégoire MC, Bottlaender M, Roumenov D, Dollé F, Bourgeois S, Penttilä J, Artiges E, Martinot JL, Trichard C. Cerebral monoamine oxidase A inhibition in tobacco smokers confirmed with PET and [11C]befloxatone. J Clin Psychopharmacol. 2009 Feb;29(1):86-8. doi: 10.1097/JCP.0b013e31819e98f. PubMed PMID: 19142115.

7: Emilien G. Befloxatone (Synthelabo). IDrugs. 1999 Mar;2(3):247-53. PubMed PMID: 16160936.

8: Valette H, Bottlaender M, Dollé F, Coulon C, Ottaviani M, Syrota A. 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. J Pharmacol Exp Ther. 2005 Jul;314(1):431-6. Epub 2005 Apr 15. PubMed PMID: 15833896.

9: Dolle F, Valette H, Bramoulle Y, Guenther I, Fuseau C, Coulon C, Lartizien C, Jegham S, George P, Curet O, Pinquier JL, Bottlaender M. Synthesis and in vivo imaging properties of [11C]befloxatone: a novel highly potent positron emission tomography ligand for mono-amine oxidase-A. Bioorg Med Chem Lett. 2003 May 19;13(10):1771-5. PubMed PMID: 12729662.

10: Bottlaender M, Dolle F, Guenther I, Roumenov D, Fuseau C, Bramoulle Y, Curet O, Jegham J, Pinquier JL, George P, Valette H. Mapping the cerebral monoamine oxidase type A: positron emission tomography characterization of the reversible selective inhibitor [11C]befloxatone. J Pharmacol Exp Ther. 2003 May;305(2):467-73. Epub 2003 Feb 11. PubMed PMID: 12606609.

11: Wouters J, Moureau F, Evrard G, Koenig JJ, Jegham S, George P, Durant F. A reversible monoamine oxidase A inhibitor, befloxatone: structural approach of its mechanism of action. Bioorg Med Chem. 1999 Aug;7(8):1683-93. PubMed PMID: 10482460.

12: Moser PC, Sanger DJ. 5-HT1A receptor antagonists neither potentiate nor inhibit the effects of fluoxetine and befloxatone in the forced swim test in rats. Eur J Pharmacol. 1999 May 14;372(2):127-34. PubMed PMID: 10395092.

13: Rosenzweig P, Patat A, Curet O, Durrieu G, Dubruc C, Zieleniuk I, Legangneux E. Clinical pharmacology of befloxatone: a brief review. J Affect Disord. 1998 Dec;51(3):305-12. PubMed PMID: 10333984.

14: Curet O, Damoiseau-Ovens G, Sauvage C, Sontag N, Avenet P, Depoortere H, Caille D, Bergis O, Scatton B. Preclinical profile of befloxatone, a new reversible MAO-A inhibitor. J Affect Disord. 1998 Dec;51(3):287-303. Review. PubMed PMID: 10333983.

15: Rosenzweig P, Patat A, Zieleniuk I, Cimarosti I, Allain H, Gandon JM. Cognitive performance in elderly subjects after a single dose of befloxatone, a new reversible selective monoamine oxidase A inhibitor. Clin Pharmacol Ther. 1998 Aug;64(2):211-22. PubMed PMID: 9728902.

16: Haddjeri N, De Montigny C, Curet O, Blier P. Effect of the reversible monoamine oxidase-A inhibitor befloxatone on the rat 5-hydroxytryptamine neurotransmission. Eur J Pharmacol. 1998 Feb 19;343(2-3):179-92. PubMed PMID: 9570466.

17: Griebel G, Perrault G, Sanger DJ. Behavioural profiles of the reversible monoamine-oxidase-A inhibitors befloxatone and moclobemide in an experimental model for screening anxiolytic and anti-panic drugs. Psychopharmacology (Berl). 1997 May;131(2):180-6. PubMed PMID: 9201807.

18: Warot D, Berlin I, Patat A, Durrieu G, Zieleniuk I, Puech AJ. Effects of befloxatone, a reversible selective monoamine oxidase-A inhibitor, on psychomotor function and memory in healthy subjects. J Clin Pharmacol. 1996 Oct;36(10):942-50. PubMed PMID: 8930782.

19: Caille D, Bergis OE, Fankhauser C, Gardes A, Adam R, Charieras T, Grosset A, Rovei V, Jarreau FX. Befloxatone, a new reversible and selective monoamine oxidase-A inhibitor. II. Pharmacological profile. J Pharmacol Exp Ther. 1996 Apr;277(1):265-77. PubMed PMID: 8613929.

20: Curet O, Damoiseau G, Aubin N, Sontag N, Rovei V, Jarreau FX. Befloxatone, a new reversible and selective monoamine oxidase-A inhibitor. I. Biochemical profile. J Pharmacol Exp Ther. 1996 Apr;277(1):253-64. PubMed PMID: 8613928.