Imipraminoxide

Chemical compound From Wikipedia, the free encyclopedia

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.[3][4][5][6]

Trade namesImiprex, Elepsin
ATC code
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Quick facts Clinical data, Trade names ...
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)[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-lifeIntravenous: 1.8 hours[2]
Identifiers
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC19H24N2O
Molar mass296.414 g·mol−1
Close

Imipraminoxide is both an analogue and a metabolite of imipramine, and has similar effects.[7][8][9][10] 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.[7][8][9][10][11][12]

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.[11][12]

Imipraminoxide has been said to be a prodrug of imipramine.[13]

See also

References

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