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Flazalone

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NSAID and cocaine addiction agent. Pharmaceutical compound
Flazalone
Clinical data
Other namesFlumefenine, R-760.
Identifiers
IUPAC name
  • (4-fluorophenyl)-methanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H19F2NO2
Molar mass331.363 g·mol
3D model (JSmol)
SMILES
  • CN1CCC(C(C1)C(=O)C2=CC=C(C=C2)F)(C3=CC=C(C=C3)F)O
InChI
  • InChI=1S/C19H19F2NO2/c1-22-11-10-19(24,14-4-8-16(21)9-5-14)17(12-22)18(23)13-2-6-15(20)7-3-13/h2-9,17,24H,10-12H2,1H3
  • Key:PPQZABOURJVKNI-UHFFFAOYSA-N

Flazalone is an anti-inflammatory substance that has not been approved as a drug.

According to Shaomeng Wang and co-workers, replacement of the para-fluoro halogen with a meta,para-dichloro substitution resulted in dopamine reuptake inhibitors useful in treating cocaine addiction.

References

  1. "Flazalone". Inxight Drugs. The National Center for Advancing Translational Sciences (NCATS).
  2. Wang S, Sakamuri S, Enyedy IJ, Kozikowski AP, Deschaux O, Bandyopadhyay BC, Tella SR, Zaman WA, Johnson KM (February 2000). "Discovery of a novel dopamine transporter inhibitor, 4-hydroxy-1-methyl-4-(4-methylphenyl)-3-piperidyl 4-methylphenyl ketone, as a potential cocaine antagonist through 3D-database pharmacophore searching. Molecular modeling, structure-activity relationships, and behavioral pharmacological studies". Journal of Medicinal Chemistry. 43 (3): 351–60. doi:10.1021/jm990516x. PMID 10669562.
  3. Wang S, Sakamuri S, Enyedy IJ, Kozikowski AP, Zaman WA, Johnson KM (July 2001). "Molecular modeling, structure--activity relationships and functional antagonism studies of 4-hydroxy-1-methyl-4-(4-methylphenyl)-3-piperidyl 4-methylphenyl ketones as a novel class of dopamine transporter inhibitors". Bioorganic & Medicinal Chemistry. 9 (7): 1753–64. doi:10.1016/s0968-0896(01)00090-6. PMID 11425577.


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