Chemistry:Imipraminoxide

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Short description: Chemical compound
Imipraminoxide
Skeletal formula of imipraminoxide
Ball-and-stick model of the imipraminoxide molecule
Clinical data
Trade namesImiprex, Elepsin
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-lifeIntravenous: 1.8 hours[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC19H24N2O
Molar mass296.414 g·mol−1

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 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. ↑ "Dibenzazepine and Related Tricyclic Compounds". Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. 4 February 2013. pp. 311–. ISBN 978-3-527-64565-7. https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA311. 
  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. https://books.google.com/books?id=5GpcTQD_L2oC&q=imipraminoxide&pg=PA546. 
  3. ↑ Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 3877. ISBN 0-412-54090-8. https://books.google.com/books?id=rWt8RTCJK1EC&q=imipraminoxide&pg=PA3877. 
  4. ↑ "Imipramine-N-oxide: preliminary investigation of a new antidepressive drug". The American Journal of Psychiatry 120 (3): 277–278. September 1963. doi:10.1176/ajp.120.3.277. PMID 13944543. 
  5. ↑ "[Imiprex "Dumex" (imipramine oxide). A new tricyclic antidepressive agent]" (in no). Tidsskrift for den Norske Laegeforening 91 (31): 2267–2268. November 1971. PMID 5133241. 
  6. ↑ 6.0 6.1 "Comparative trial of imipramine N-oxide and imipramine in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica 49 (1): 77–90. 1973. doi:10.1111/j.1600-0447.1973.tb04400.x. PMID 4572170. 
  7. ↑ 7.0 7.1 Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. 2008. p. 34. ISBN 978-0-444-53266-4. https://books.google.com/books?id=s0XYvuPVgaAC&q=imipraminoxide&pg=PA34. 
  8. ↑ 8.0 8.1 "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]" (in sv). Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry 25 (5): 463–470. 1971. doi:10.3109/08039487109094696. PMID 4947298. 
  9. ↑ 9.0 9.1 Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Hagerstown, MD: Lippincott Williams & Wilkins. 2004. p. 87. ISBN 0-7817-3481-9. https://books.google.com/books?id=CeibVy3-LSMC&q=%22imipramine+N-oxide%22&pg=PA87. 
  10. ↑ 10.0 10.1 "Investigation of the orthostatic reaction after intravenous administration of imipramine, chlorimipramine, and inimpramine-N-oxide". Acta Psychiatrica Scandinavica 54 (1): 74–78. July 1976. doi:10.1111/j.1600-0447.1976.tb00095.x. PMID 952235. 
  11. ↑ 11.0 11.1 "Assessment of the anticholinergic effects of antidepressants in a single-dose cross-over study of salivation and plasma levels". Psychopharmacology 82 (4): 348–354. 1984. doi:10.1007/BF00427684. PMID 6427827. 
  12. ↑ "Central Nervous System Drugs". Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. 23 February 2012. pp. 302–. ISBN 978-3-527-64632-6. https://books.google.com/books?id=f-XHh17NfwgC&pg=PA302. 



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