Amitriptylinoxide

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
  • 3-(10,11-dihydro- 5H-dibenzo[a,d]cycloheptene- 5-ylidene)- N,N-dimethyl- 1-propanamine N-oxide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.550 Edit this at Wikidata
Chemical and physical data
FormulaC20H23NO
Molar mass293.410 g·mol−1
3D model (JSmol)
  • [O-][N+](C)(C)CC/C=C2/c1c(cccc1)CCc3c2cccc3
  • InChI=1S/C20H23NO/c1-21(2,22)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3 checkY
  • Key:ZPMKQFOGINQDAM-UHFFFAOYSA-N checkY
  (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]

  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. ^ a b 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. S2CID 12666498.
  3. ^ a b 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. S2CID 956047.
  4. ^ a b 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. doi:10.3109/08039487109094663. PMID 4945956.
  5. ^ a b 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.
  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. doi:10.3109/08039487109094696. 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. S2CID 31927039.
  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. S2CID 25823571.
  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.
  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.