Medifoxamine

Medifoxamine
Clinical data
Trade namesClédial, Gerdaxyl
Other namesMedifoxamine fumarate; N,N-Dimethyl-2,2-diphenoxyethylamine
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability21%[1][2]
Elimination half-life2.8 hours (acute);[1][2]
4.0 hours (chronic)[3]
Identifiers
  • N,N-dimethyl-2,2-diphenoxyethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.046.359 Edit this at Wikidata
Chemical and physical data
FormulaC16H19NO2
Molar mass257.333 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CN(C)CC(OC1=CC=CC=C1)OC2=CC=CC=C2
  • InChI=1S/C16H19NO2/c1-17(2)13-16(18-14-9-5-3-6-10-14)19-15-11-7-4-8-12-15/h3-12,16H,13H2,1-2H3
  • Key:QNMGHBMGNRQPNL-UHFFFAOYSA-N
  (verify)

Medifoxamine, previously sold under the brand names Clédial and Gerdaxyl, is an atypical antidepressant[4] with additional anxiolytic properties[5] acting via dopaminergic and serotonergic mechanisms which was formerly marketed in France and Spain, as well as Morocco.[6][7][8][9][10] The drug was first introduced in France sometime around 1990.[11] It was withdrawn from the market in 1999 (Morocco) and 2000 (France) following incidences of hepatotoxicity.[10][12][13]

  1. ^ a b Saleh S, Johnston A, Turner P (October 1990). "Absolute bioavailability and pharmacokinetics of medifoxamine in healthy humans". British Journal of Clinical Pharmacology. 30 (4): 621–4. doi:10.1111/j.1365-2125.1990.tb03823.x. PMC 1368255. PMID 2291875.
  2. ^ a b Dörwald FZ (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 259–. ISBN 978-3-527-64565-7.
  3. ^ Gainsborough N, Nelson ML, Maskrey V, Swift CG, Jackson SH (1994). "The pharmacokinetics and pharmacodynamics of medifoxamine after oral administration in healthy elderly volunteers". European Journal of Clinical Pharmacology. 46 (2): 163–6. doi:10.1007/bf00199882. PMID 8039537. S2CID 6978939.
  4. ^ Holroyd-Leduc J, Reddy M (9 March 2012). Evidence-Based Geriatric Medicine. John Wiley & Sons. pp. 299–. ISBN 978-1-118-28181-9.
  5. ^ Annual Reports in Medicinal Chemistry. Vol. 22. Academic Press. 2 September 1987. pp. 323–. ISBN 978-0-08-058366-2.
  6. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 759–. ISBN 978-1-4757-2085-3.
  7. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 638–. ISBN 978-3-88763-075-1.
  8. ^ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9.
  9. ^ Mitchell PB (1995). "Novel French antidepressants not available in the United States". Psychopharmacology Bulletin. 31 (3): 509–19. PMID 8668756.
  10. ^ a b Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments. United Nations Publications. 2003. pp. 135–136. ISBN 978-92-1-130230-1.
  11. ^ Saleh S, Johnston A, Edeki T, Turner P (April 1990). "Tolerability and kinetics of intravenous medifoxamine in healthy volunteers". International Clinical Psychopharmacology. 5 (2): 97–102. doi:10.1097/00004850-199004000-00003. PMID 2380545.
  12. ^ Dumortier G, Cabaret W, Stamatiadis L, Saba G, Benadhira R, Rocamora JF, et al. (2002). "[Hepatic tolerance of atypical antipsychotic drugs]". L'Encéphale (in French). 28 (6 Pt 1): 542–51. PMID 12506267.
  13. ^ Papakostas GI, Fava M (2010). Pharmacotherapy for Depression and Treatment-resistant Depression. World Scientific. pp. 88–. ISBN 978-981-4287-59-3.