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Imipraminoxide

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical 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)[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Eliminationhalf-lifeIntravenous: 1.8 hours[2]
Identifiers
  • 3-(5,6-dihydrobenzo[b][f]benzazepin- 11-yl)-N,N-dimethyl- propan- 1-amineN-oxide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.027.188Edit this at Wikidata
Chemical and physical data
FormulaC19H24N2O
Molar mass296.414 g·mol−1

Imipraminoxide (brand namesImiprex,Elepsin), orimipramineN-oxide, is atricyclic antidepressant (TCA) that was introduced inEurope in the 1960s for the treatment ofdepression.[3][4][5][6]

Imipraminoxide is both ananalogue and ametabolite ofimipramine, and has similar effects.[7][8][9][10] However, inclinical trials, imipraminoxide was found to have a faster onset of action, slightly higher efficacy, and fewer and less markedside effects, including diminishedorthostatic hypotension andanticholinergic effects likedry mouth,sweating,dizziness, andfatigue.[7][8][9][10][11][12]

Imipraminoxide'spharmacology has not been well elucidated, but based on its very close relationship with imipramine, it likely acts as aserotonin andnorepinephrine reuptake inhibitor andserotonin,adrenenaline,histamine, andmuscarinic acetylcholine receptorantagonist, though with weakerantiadrenergic andanticholinergic actions.[11][12]

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

See also

[edit]

References

[edit]
  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. Retrieved2023-08-16.
  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). "[Imiprex "Dumex" (imipramine oxide). A new tricyclic antidepressive agent]".Tidsskrift for den Norske Laegeforening (in Norwegian).91 (31):2267–2268.PMID 5133241.
  7. ^abRapp 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. ^abAronson JK (2008).Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 34.ISBN 978-0-444-53266-4.
  9. ^abDencker SJ (1971). "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]".Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Swedish).25 (5):463–470.doi:10.3109/08039487109094696.PMID 4947298.
  10. ^abBeale 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. ^abDencker 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. ^abClemmesen 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.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
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SMSTooltip Serotonin modulator and stimulators
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