Oxaflozane

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Oxaflozane
Oxaflozane.svg
Systematic (IUPAC) name
4-Propan-2-yl-2-[3-(trifluoromethyl)phenyl]morpholine
Clinical data
Trade names Conflictan
Routes of
administration
Oral
Legal status
  • ℞ (Prescription only)
Identifiers
CAS Number 26629-86-8
26629-86-7 (HCl)
ATC code N06AX10 (WHO)
PubChem CID 432824
ChemSpider 382782
UNII V4WLW77V5Q YesY
KEGG D07340
Synonyms CERM-1766
Chemical data
Formula C14H18F3NO
Molar mass 273.29 g/mol

Oxaflozane (INN) (brand name Conflictan) is an antidepressant and anxiolytic drug that was introduced by Solvay in France in 1982 for the treatment of depression but has since been discontinued.[1][2][3][4] It is a prodrug of flumexadol (N-dealkyloxaflozane; 2-(3-trifluoromethylphenyl)morpholine; CERM-1841 or 1841-CERM), which is reported to act as an agonist of the serotonin 5-HT1A (pKi = 7.1) and 5-HT2C (pKi = 7.5) receptors and, to a much lesser extent, of the 5-HT2A (pKi = 6.0) receptor.[4][5] In addition to its serotonergic properties, oxaflozane may also produce anticholinergic side effects at high doses, such as in overdose.[6]

Flumexadol — the primary metabolite of oxaflozane. It has been described as a non-opioid analgesic.[7][8][9]

See also[edit]

References[edit]

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 909–. ISBN 978-1-4757-2085-3. 
  2. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 766. ISBN 3-88763-075-0. 
  3. ^ Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. p. 1122. ISBN 0-8155-1144-2. 
  4. ^ a b Jean-Pierre Bégué; Daniele Bonnet-Delpon (2 June 2008). Bioorganic and Medicinal Chemistry of Fluorine. John Wiley & Sons. pp. 303–. ISBN 978-0-470-28187-1. 
  5. ^ Leysen DC (February 1999). "Selective 5-HT2C agonists as potential antidepressants". IDrugs : the Investigational Drugs Journal 2 (2): 109–20. PMID 16160946. 
  6. ^ Dutertre JP, Barbier P, Suc AL, Jonville AP, Autret E (1992). "Oxaflozane overdose in a child". Journal of Toxicology. Clinical Toxicology 30 (1): 123–6. doi:10.3109/15563659208994452. PMID 1542141. 
  7. ^ Hache J, Diamantis W, Sofia D, Streichenberger G (1978). "The pharmacology of 1841 CERM, a new analgesic". Arzneimittelforschung 28 (4): 642–5. PMID 312104. 
  8. ^ Kucharczyk, N.; Yang, J. T.; Valia, K. H.; Stiefel, F. J.; Sofia, R. D. (1979). "Metabolites of 2-(3-Trifluoromethylphenyl)Tetrahydro-1,4-Oxazine (Cerm 1841) in Rats and Dogs". Xenobiotica 9 (11): 703–711. doi:10.3109/00498257909042338. ISSN 0049-8254. 
  9. ^ Nilsson, Björn M. (2006). "5-Hydroxytryptamine 2C (5-HT2C) Receptor Agonists as Potential Antiobesity Agents". Journal of Medicinal Chemistry 49 (14): 4023–4034. doi:10.1021/jm058240i. ISSN 0022-2623. 

Further reading[edit]

  • Rascol A, Maurel H, David J, Layani M (1974). "[Preliminary clinical results of a new non tricyclic antidepressive drug: oxaflozane]". Thérapie (in French) 29 (1): 95–9. PMID 4603757. 
  • Hache J, Duchene-Marullaz P, Streichenberger G (1974). "[Pharmacological profile of a new non tricyclic antidepressant: oxaflozane (1,766 Cerm)]". Thérapie (in French) 29 (1): 81–93. PMID 4849381. 
  • Constantin M, Pognat JF (1979). "Comparative study of oxaflozane urinary metabolism in man, the dog and the rat. Identification of the principal metabolites". Arzneimittel-Forschung 29 (1): 109–14. PMID 582104. 
  • Bertolino A, palermo M, Porro V (1985). "Oxaflozane, a new nontricyclic antidepressant in the treatment of anxiety-depressions syndromes.". Acta Ther (11): 209–218. 
  • Aguglia E (1986). "On the therapetic value of axaflozane: Its application in the treatment of emotional disturbances of the anxious-depressive type accompanied by somatic manifestations.". Acta Ther (12): 259–267.