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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) In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	Intravenous: 1.8 hours
Identifiers
IUPAC name 3-(5,6-dihydrobenzobenzazepin- 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

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.

Imipraminoxide is both an analogue and a metabolite of imipramine, and has similar effects. 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.

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.

Imipraminoxide has been said to be a prodrug of imipramine.

See also

• Amitriptylinoxide

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Dörwald FZ (4 February 2013). "Dibenzazepine and Related Tricyclic Compounds". Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 311–. ISBN 978-3-527-64565-7.
3. 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.
4. Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 3877. ISBN 0-412-54090-8.
5. 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): 277–278. doi:10.1176/ajp.120.3.277. PMID 13944543.
6. Lingjaerde O (November 1971). "". Tidsskrift for den Norske Laegeforening (in Norwegian). 91 (31): 2267–2268. PMID 5133241.
7. ^ 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.
8. ^ Aronson JK (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 34. ISBN 978-0-444-53266-4.
9. ^ Dencker SJ (1971). "". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Swedish). 25 (5): 463–470. doi:10.3109/08039487109094696. PMID 4947298.
10. ^ Beale JM, Wilson CH, Gisvold O, Block JH (2004). Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Hagerstown, MD: Lippincott Williams & Wilkins. p. 87. ISBN 0-7817-3481-9.
11. ^ 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): 74–78. doi:10.1111/j.1600-0447.1976.tb00095.x. PMID 952235. S2CID 13172168.
12. ^ 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): 348–354. doi:10.1007/BF00427684. PMID 6427827. S2CID 5970487.
13. Baumann P, Hiemke C (23 February 2012). "Central Nervous System Drugs". In Anzenbacher P, Zanger UM (eds.). Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 302–. ISBN 978-3-527-64632-6.

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