Amitriptylinoxide

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Amitriptylinoxide
Amitriptylinoxide.png
Systematic (IUPAC) name
3-(10,11-dihydro- 5H-dibenzo[a,d]cycloheptene- 5-ylidene)- N,N-dimethyl- 1-propanamine N-oxide
Clinical data
Legal status Prescription only
Routes Oral
Identifiers
CAS number 4317-14-0 YesY
ATC code None
PubChem CID 20313
ChemSpider 19137 YesY
UNII TYR2U59WMA YesY
KEGG D07449 YesY
ChEMBL CHEMBL627 YesY
Chemical data
Formula C20H23NO 
Mol. mass 293.40 g/mol
 YesY (what is this?)  (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][3][4][5][6]

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.[3][7][8]

See also[edit]

References[edit]

  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. 
  3. ^ a b c d 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. ^ 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. 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 0-444-53266-8. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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.