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Amitriptylinoxide

Chemical compound

Chemical compound

Amitriptylinoxide (brand names Amioxid, Ambivalon, Equilibrin), or amitriptyline N-oxide, is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.

Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant. However, it has a faster onset of action and fewer adverse effects, including reduced drowsiness, sedation, anticholinergic symptoms like dry mouth, sweating, and dizziness, orthostatic hypotension, and cardiotoxicity.

In receptor binding assays, amitriptylinoxide was found to have generally equivalent pharmacology to amitriptyline, acting as a serotonin and norepinephrine reuptake inhibitor, serotonin receptor antagonist, and H1 receptor antagonist, among other properties, but with approximately 60-fold lower affinity for the α1-adrenergic receptor, and the weakest affinity of any of the TCAs analyzed for the muscarinic acetylcholine receptors.

Amitriptylinoxide has been said to be a prodrug of amitriptyline.

References

References

  1. Swiss Pharmaceutical Society. (2000). "Index Nominum 2000: International Drug Directory (Book with CD-ROM)". Medpharm Scientific Publishers.
  2. Rapp W. (September 1978). "Comparative trial of amitriptyline-N-oxide and amitriptyline in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica.
  3. (January 1990). "Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline". Pharmacopsychiatry.
  4. (1971). "[Amitriptyline N-oxide. A new antidepressant. A clinical double-blind trial in comparison with amitriptyline]". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry.
  5. Aronson, Jeffrey Kenneth. (2008). "Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects)". Elsevier Science.
  6. (1978). "Central nervous effects of a new tricyclic antidepressant (amitriptylinoxide)". Arzneimittel-Forschung.
  7. Dencker SJ. (1971). "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry.
  8. (September 1985). "Amitriptylinoxide: receptor-binding profile compared with other antidepressant drugs". Pharmacopsychiatry.
  9. (November 1982). "Central action of amitriptyline N-oxide". Pharmacopsychiatria.
  10. (July 1980). "Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites". Acta Pharmacologica et Toxicologica.
  11. (23 February 2012). "Metabolism of Drugs and Other Xenobiotics". John Wiley & Sons.
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amine-oxides dibenzocycloheptenes dimethylamino-compounds muscarinic-antagonists tricyclic-antidepressants
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