Amitriptylinoxide

Amitriptylinoxide
Skeletal formula of amitriptylinoxide
Ball-and-stick model of the amitriptylinoxide molecule
Clinical data
Routes of
administration
Oral
ATC code none
Legal status
Legal status
  • ℞ (Prescription only)
Identifiers
CAS Number 4317-14-0 YesY
PubChem (CID) 20313
ChemSpider 19137 YesY
UNII TYR2U59WMA YesY
KEGG D07449 YesY
ChEMBL CHEMBL627 YesY
Chemical and physical data
Formula C20H23NO
Molar mass 293.40 g/mol
3D model (Jmol) Interactive image
  (verify)

Amitriptylinoxide (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, amitripylinoxide 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]

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.
  2. 1 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. 58 (3): 245–55. doi:10.1111/j.1600-0447.1978.tb06936.x. PMID 360779.
  3. 1 2 Tegeler J, Klieser E, Lehmann E, Heinrich K (January 1990). "Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline". Pharmacopsychiatry. 23 (1): 45–9. doi:10.1055/s-2007-1014481. PMID 2179974.
  4. 1 2 Godt HH, Fredslund-Andersen K, Edlund AH (1971). "[Amitriptyline N-oxide. A new antidepressant. A clinical double-blind trial in comparison with amitriptyline]". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Danish). 25 (3): 237–46. PMID 4945956.
  5. 1 2 Aronson, Jeffrey Kenneth (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 30. ISBN 0-444-53266-8.
  6. Wenzl H, Graf E, Sieck A (1978). "Central nervous effects of a new tricyclic antidepressant (amitriptylinoxide)". Arzneimittel-Forschung. 28 (10b): 1874–9. PMID 261811.
  7. Dencker SJ (1971). "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Swedish). 25 (5): 463–70. PMID 4947298.
  8. Borbe HO, Zierenberg O (September 1985). "Amitriptylinoxide: receptor-binding profile compared with other antidepressant drugs". Pharmacopsychiatry. 18 (5): 314–9. doi:10.1055/s-2007-1017388. PMID 2996040.
  9. Maj J, Vetulani J, Michaluk J, Rogóz Z, Skuza G (November 1982). "Central action of amitriptyline N-oxide". Pharmacopsychiatria. 15 (6): 187–91. doi:10.1055/s-2007-1019536. PMID 6185962.
  10. Hyttel J, Christensen AV, Fjalland B (July 1980). "Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites". Acta Pharmacologica et Toxicologica. 47 (1): 53–7. doi:10.1111/j.1600-0773.1980.tb02025.x. PMID 7395525.
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