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

Imipraminoxide

Clinical data
Trade names	Imiprex, Elepsin
Routes of administration	Oral
ATC code	N06AA03 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	Intravenous: 1.8 hours[2]
Identifiers
IUPAC name 3-(5,6-dihydrobenzo[b][f]benzazepin- 11-yl)- N,N-dimethyl- propan- 1-amine N-oxide
CAS Number	6829-98-7
PubChem CID	65589
ChemSpider	59031
UNII	8MKS280XJW
KEGG	D07334
ChEMBL	ChEMBL1614644
CompTox Dashboard (EPA)	DTXSID40218445
ECHA InfoCard	100.027.188
Chemical and physical data
Formula	C19H24N2O
Molar mass	296.414 g·mol−1

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

• Amitriptylinoxide