Chemistry:Amitriptylinoxide

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Short description: Chemical compound
Amitriptylinoxide
Skeletal formula of amitriptylinoxide
Ball-and-stick model of the amitriptylinoxide molecule
Clinical data
Trade namesAmioxid, Ambivalon, Equilibrin
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC20H23NO
Molar mass293.410 g·mol−1
3D model (JSmol)
  (verify)

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.[1]

Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant.[2][3][4][5] 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.[2][3][4][5][6][7]

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.[8][9][10]

Amitriptylinoxide has been said to be a prodrug of amitriptyline.[11]

See also

References

  1. ↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 49. ISBN 3-88763-075-0. https://books.google.com/books?id=5GpcTQD_L2oC&q=amitriptylinoxide&pg=PA49. 
  2. ↑ 2.0 2.1 Rapp W (September 1978). "Comparative trial of amitriptyline-N-oxide and amitriptyline in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica 58 (3): 245–55. doi:10.1111/j.1600-0447.1978.tb06936.x. PMID 360779. 
  3. ↑ 3.0 3.1 "Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline". Pharmacopsychiatry 23 (1): 45–9. January 1990. doi:10.1055/s-2007-1014481. PMID 2179974. 
  4. ↑ 4.0 4.1 "[Amitriptyline N-oxide. A new antidepressant. A clinical double-blind trial in comparison with amitriptyline]" (in da). Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry 25 (3): 237–46. 1971. doi:10.3109/08039487109094663. PMID 4945956. 
  5. ↑ 5.0 5.1 Aronson, Jeffrey Kenneth (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 30. ISBN 978-0-444-53266-4. https://books.google.com/books?id=s0XYvuPVgaAC&q=amitriptylinoxide&pg=PA30. 
  6. ↑ "Central nervous effects of a new tricyclic antidepressant (amitriptylinoxide)". Arzneimittel-Forschung 28 (10b): 1874–9. 1978. PMID 261811. 
  7. ↑ Dencker SJ (1971). "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]" (in sv). Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry 25 (5): 463–70. doi:10.3109/08039487109094696. PMID 4947298. 
  8. ↑ "Amitriptylinoxide: receptor-binding profile compared with other antidepressant drugs". Pharmacopsychiatry 18 (5): 314–9. September 1985. doi:10.1055/s-2007-1017388. PMID 2996040. 
  9. ↑ "Central action of amitriptyline N-oxide". Pharmacopsychiatria 15 (6): 187–91. November 1982. doi:10.1055/s-2007-1019536. PMID 6185962. 
  10. ↑ "Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites". Acta Pharmacologica et Toxicologica 47 (1): 53–7. July 1980. doi:10.1111/j.1600-0773.1980.tb02025.x. PMID 7395525. 
  11. ↑ Pavel Anzenbacher; Ulrich M. Zanger (23 February 2012). Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 302–. ISBN 978-3-527-64632-6. https://books.google.com/books?id=f-XHh17NfwgC&pg=PA302. 



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