Tofenacin

Tofenacin 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. Tofenacin is also 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]

Tofenacin
Clinical data
Trade namesElamol, Tofacine, Tofalin
Other namestofenacin hydrochloride (USAN US)
Routes of
administration		By mouth
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • N-methyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.035.746
Chemical and physical data
FormulaC17H21NO
Molar mass255.361 g·mol−1
3D model (JSmol)
SMILES
  • O(CCNC)C(c1ccccc1)c2ccccc2C
InChI
  • InChI=1S/C17H21NO/c1-14-8-6-7-11-16(14)17(19-13-12-18-2)15-9-4-3-5-10-15/h3-11,17-18H,12-13H2,1-2H3
  • Key:PNYKGCPSFKLFKA-UHFFFAOYSA-N

See also

References
  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. 2013-01-15. 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. doi:10.1177/030006057600400610. PMID 800383. S2CID 40083513.
  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.



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