Tofenacin

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Tofenacin
Tofenacin structure.png
Systematic (IUPAC) name
N-methyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanamine
Clinical data
  • (Prescription only)
Identifiers
15301-93-6
10488-36-5 (HCl)
None
PubChem CID 25315
ChemSpider 23647
Chemical data
Formula C17H21NO
255.355 g/mol

Tofenacin (INN; Elamol, Tofacine, Tofalin), or tofenacin hydrochloride (USAN), also sometimes called mono-N-desmethylorphenadrine, is an antidepressant drug with a tricyclic-like structure which was developed and marketed in the United Kingdom and Italy in 1971 and 1981, respectively, by Brocades-Stheeman & Pharmacia (now part of Astellas Pharma).[1][2][3] It acts as a serotonin-norepinephrine reuptake inhibitor,[4] and based on its close relation to orphenadrine, may also possess anticholinergic and antihistamine properties. In addition to its use as a pharmaceutical medication, tofenacin is the major active metabolite of orphenadrine and likely plays a role in its beneficial effects against depressive symptoms seen in Parkinson's disease patients.[5][6]

Synthesis[edit]

Tofenacin synthesis: Harms August Franciscus; Koninklijke Pharma Fab Nv; U.S. Patent 3,407,258 (1964).

According to Lednicer, a second method is to react benzhydrol with ethyl bromoacetate to form α-alkoxyester, saponify, form methylamide, then reduce with LAH.

See also[edit]

References[edit]

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 1041. ISBN 978-3-88763-075-1. Retrieved 19 May 2012. 
  2. ^ J. Buckingham (1996). Dictionary of organic compounds: Chemical Abstracts Service registry number index. CRC Press. p. 6074. ISBN 978-0-412-54090-5. Retrieved 19 May 2012. 
  3. ^ Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. p. 3268. ISBN 978-0-8155-1526-5. Retrieved 19 May 2012. 
  4. ^ Gwynn Pennant Ellis; Geoffrey Buckle West (1 January 1978). Progress in Medicinal Chemistry. Elsevier. p. 284. ISBN 978-0-7204-0655-9. Retrieved 19 May 2012. 
  5. ^ Capstick N, Pudney H (1976). "A comparative trial of orphenadrine and tofenacin in the control of depression and extrapyramidal side-effects associated with fluphenazine decanoate therapy". The Journal of International Medical Research 4 (6): 435–40. PMID 800383. 
  6. ^ Altamura AC, Mauri MC, De Novellis F, Percudani M, Vampini V (November 1989). "Residual neuroleptic-induced parkinsonian symptoms in schizophrenia. A naturalistic study with orphenadrine". Pharmacopsychiatry 22 (6): 246–9. doi:10.1055/s-2007-1014608. PMID 2616635.