Imipraminoxide

Imipraminoxide (brand names Imiprex, Elepsin), or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression.[2][3][4][5]

Imipraminoxide
Clinical data
Trade namesImiprex, Elepsin
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-lifeIntravenous: 1.8 hours[1]
Identifiers
IUPAC name
  • 3-(5,6-dihydrobenzo[b][f]benzazepin- 11-yl)- N,N-dimethyl- propan- 1-amine N-oxide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.027.188
Chemical and physical data
FormulaC19H24N2O
Molar mass296.414 g·mol−1

Imipraminoxide is both an analogue and a metabolite of imipramine, and has similar effects.[6][7][8][9] However, in clinical trials, imipraminoxide was found to have a faster onset of action, slightly higher efficacy, and fewer and less marked side effects, including diminished orthostatic hypotension and anticholinergic effects like dry mouth, sweating, dizziness, and fatigue.[6][7][8][9][10][11]

Imipraminoxide's pharmacology has not been well elucidated, but based on its very close relationship with imipramine, it likely acts as a serotonin and norepinephrine reuptake inhibitor and serotonin, adrenenaline, histamine, and muscarinic acetylcholine receptor antagonist, though with weaker antiadrenergic and anticholinergic actions.[10][11]

Imipraminoxide has been said to be a prodrug of imipramine.[12]

See also

References
  1. Florencio Zaragoza Dörwald (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 311–. ISBN 978-3-527-64565-7.
  2. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 546. ISBN 3-88763-075-0.
  3. Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 3877. ISBN 0-412-54090-8.
  4. FAURBYE A, JACOBSEN O, KRISTJANSEN P, MUNKVAD I (September 1963). "Imipramine-N-oxide: preliminary investigation of a new antidepressive drug". The American Journal of Psychiatry. 120 (3): 277–8. doi:10.1176/ajp.120.3.277. PMID 13944543.
  5. Lingjaerde O (November 1971). "[Imiprex "Dumex" (imipramine oxide). A new tricyclic antidepressive agent]". Tidsskrift for den Norske Lægeforening (in Norwegian). 91 (31): 2267–8. PMID 5133241.
  6. Rapp W, Norén MB, Pedersen F (1973). "Comparative trial of imipramine N-oxide and imipramine in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica. 49 (1): 77–90. doi:10.1111/j.1600-0447.1973.tb04400.x. PMID 4572170. S2CID 37508967.
  7. Aronson, Jeffrey Kenneth (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 34. ISBN 978-0-444-53266-4.
  8. Dencker SJ (1971). "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Swedish). 25 (5): 463–70. doi:10.3109/08039487109094696. PMID 4947298.
  9. Beale, John Marlowe; Wilson, Charles Henry; Gisvold, Ole; Block, John H. (2004). Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Hagerstwon, MD: Lippincott Williams & Wilkins. p. 87. ISBN 0-7817-3481-9.
  10. Dencker SJ, Bake B (July 1976). "Investigation of the orthostatic reaction after intravenous administration of imipramine, chlorimipramine, and inimpramine-N-oxide". Acta Psychiatrica Scandinavica. 54 (1): 74–8. doi:10.1111/j.1600-0447.1976.tb00095.x. PMID 952235. S2CID 13172168.
  11. Clemmesen L, Mikkelsen PL, Lund H, Bolwig TG, Rafaelsen OJ (1984). "Assessment of the anticholinergic effects of antidepressants in a single-dose cross-over study of salivation and plasma levels". Psychopharmacology. 82 (4): 348–54. doi:10.1007/BF00427684. PMID 6427827. S2CID 5970487.
  12. Pavel Anzenbacher; Ulrich M. Zanger (23 February 2012). Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 302–. ISBN 978-3-527-64632-6.


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