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'''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 [[Major depressive disorder|depression]].<ref name="isbn3-88763-075-0">{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | page = 49 | pages = 1932 | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA49&dq=amitriptylinoxide&as_brr=3&pg=PA49#v=onepage&q=&f=false}}</ref>
'''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 [[Major depressive disorder|depression]].<ref name="isbn3-88763-075-0">{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | page = 49 | pages = 1932 | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA49&dq=amitriptylinoxide&as_brr=3&pg=PA49#v=onepage&q=&f=false}}</ref>


Amitriptylinoxide is both an [[analogue]] and [[metabolite]] of [[amitriptyline]], and has similar effects as well as equivalent efficacy as an antidepressant.<ref name="pmid360779">{{cite journal | author = Rapp W | title = Comparative trial of amitriptyline-N-oxide and amitriptyline in the treatment of out-patients with depressive syndromes | journal = Acta Psychiatrica Scandinavica | volume = 58 | issue = 3 | pages = 245–55 | year = 1978 | month = September | pmid = 360779 | doi = | url = }}</ref><ref name="pmid">{{cite journal | author = Tegeler J, Klieser E, Lehmann E, Heinrich K | title = Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline | journal = Pharmacopsychiatry | volume = 23 | issue = 1 | pages = 45–9 | year = 1990 | month = January | pmid = | doi = | url = }}</ref><ref name="pmid4945956">{{cite journal | author = Godt HH, Fredslund-Andersen K, Edlund AH | title = [Amitriptyline N-oxide. A new antidepressant. A clinical double-blind trial in comparison with amitriptyline] | language = Danish | journal = Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry | volume = 25 | issue = 3 | pages = 237–46 | year = 1971 | pmid = 4945956 | doi = | url = }}</ref><ref name="urlMeylers Side Effects of Psychiatric … - Google Books">{{cite web | url = http://books.google.com/books?id=s0XYvuPVgaAC&lpg=PT40&dq=amitriptylinoxide&as_brr=3&pg=PT40#v=onepage&q=amitriptylinoxide&f=false | title = Meyler's Side Effects of Psychiatric … - Google Books}}</ref> However, it has a faster onset of action and fewer [[adverse effect]]s, including reduced [[drowsiness]], [[sedation]], [[anticholinergic]] symptoms like [[dry mouth]], [[sweating]], and [[dizziness]], [[orthostatic hypotension]], and [[cardiotoxicity]].<ref name="pmid360779"/><ref name="pmid"/><ref name="pmid">{{cite journal | author = Wenzl H, Graf E, Sieck A | title = Central nervous effects of a new tricyclic antidepressant (amitriptylinoxide) | journal = Arzneimittel-Forschung | volume = 28 | issue = 10b | pages = 1874–9 | year = 1978 | pmid = | doi = | url = }}</ref><ref name="pmid4945956"/><ref name="urlMeylers Side Effects of Psychiatric … - Google Books"/><ref name="pmid5354541">{{cite journal | author = Jensen PS, Bolwig T | title = [DANO (amitriptyline-N-oxide). A new antidepressive agent. A study with special reference to cardiotoxic effect] | language = Danish | journal = Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry | volume = 23 | issue = 1 | pages = 30–5 | year = 1969 | pmid = 5354541 | doi = | url = }}</ref><ref name="pmid4947298">{{cite journal | author = Dencker SJ | title = [Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide] | language = Swedish | journal = Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry | volume = 25 | issue = 5 | pages = 463–70 | year = 1971 | pmid = 4947298 | doi = | url = }}</ref>
Amitriptylinoxide is both an [[analogue]] and [[metabolite]] of [[amitriptyline]], and has similar effects as well as equivalent efficacy as an antidepressant.<ref name="pmid360779">{{cite journal | author = Rapp W | title = Comparative trial of amitriptyline-N-oxide and amitriptyline in the treatment of out-patients with depressive syndromes | journal = Acta Psychiatrica Scandinavica | volume = 58 | issue = 3 | pages = 245–55 | year = 1978 | month = September | pmid = 360779 | doi = | url = }}</ref><ref name="pmid">{{cite journal | author = Tegeler J, Klieser E, Lehmann E, Heinrich K | title = Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline | journal = Pharmacopsychiatry | volume = 23 | issue = 1 | pages = 45–9 | year = 1990 | month = January | pmid = | doi = | url = }}</ref><ref name="pmid4945956">{{cite journal | author = Godt HH, Fredslund-Andersen K, Edlund AH | title = [Amitriptyline N-oxide. A new antidepressant. A clinical double-blind trial in comparison with amitriptyline] | language = Danish | journal = Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry | volume = 25 | issue = 3 | pages = 237–46 | year = 1971 | pmid = 4945956 | doi = | url = }}</ref><ref name="isbn0-444-53266-8">{{cite book | author = Aronson, Jeffrey Kenneth | title = Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects) | publisher = Elsevier Science | location = Amsterdam | year = 2008 | page = 30 | pages = 512 | isbn = 0-444-53266-8 | oclc = | doi = | url = http://books.google.com/books?id=s0XYvuPVgaAC&lpg=PP1&dq=amitriptylinoxide&as_brr=3&pg=PA30#v=onepage&q=&f=false}}</ref> However, it has a faster onset of action and fewer [[adverse effect]]s, including reduced [[drowsiness]], [[sedation]], [[anticholinergic]] symptoms like [[dry mouth]], [[sweating]], and [[dizziness]], [[orthostatic hypotension]], and [[cardiotoxicity]].<ref name="pmid360779"/><ref name="pmid"/><ref name="pmid">{{cite journal | author = Wenzl H, Graf E, Sieck A | title = Central nervous effects of a new tricyclic antidepressant (amitriptylinoxide) | journal = Arzneimittel-Forschung | volume = 28 | issue = 10b | pages = 1874–9 | year = 1978 | pmid = | doi = | url = }}</ref><ref name="pmid4945956"/><ref name="isbn0-444-53266-8">{{cite book | author = Aronson, Jeffrey Kenneth | title = Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects) | publisher = Elsevier Science | location = Amsterdam | year = 2008 | page = 30 | pages = 512 | isbn = 0-444-53266-8 | oclc = | doi = | url = http://books.google.com/books?id=s0XYvuPVgaAC&lpg=PP1&dq=amitriptylinoxide&as_brr=3&pg=PA30#v=onepage&q=&f=false}}</ref><ref name="pmid4947298">{{cite journal | author = Dencker SJ | title = [Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide] | language = Swedish | journal = Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry | volume = 25 | issue = 5 | pages = 463–70 | year = 1971 | pmid = 4947298 | doi = | url = }}</ref>


In [[receptor (biochemistry)|receptor]] [[binding (molecular)|binding]] assays, amitripylinoxide was found to have generally equivalent [[pharmacology]] to amitriptyline, acting as a [[serotonin reuptake inhibitor|serotonin]] and [[norepinephrine reuptake inhibitor]], [[serotonin receptor antagonist]], and [[H1 receptor antagonist|H<sub>1</sub> receptor antagonist]], among other properties, but with approximately 60-fold lower [[affinity (pharmacology)|affinity]] for the [[alpha-adrenergic receptor|α<sub>1</sub>-adrenergic receptor]], and the weakest affinity of any of the TCAs analyzed for the [[muscarinic acetylcholine receptor]]s.<ref name="pmid">{{cite journal | author = Borbe HO, Zierenberg O | title = Amitriptylinoxide: receptor-binding profile compared with other antidepressant drugs | journal = Pharmacopsychiatry | volume = 18 | issue = 5 | pages = 314–9 | year = 1985 | month = September | pmid = | doi = | url = }}</ref><ref name="pmid6185962">{{cite journal | author = Maj J, Vetulani J, Michaluk J, Rogóz Z, Skuza G | title = Central action of amitriptyline N-oxide | journal = Pharmacopsychiatria | volume = 15 | issue = 6 | pages = 187–91 | year = 1982 | month = November | pmid = 6185962 | doi = | url = }}</ref><ref name="pmid7395525">{{cite journal | author = Hyttel J, Christensen AV, Fjalland B | title = Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites | journal = Acta Pharmacologica Et Toxicologica | volume = 47 | issue = 1 | pages = 53–7 | year = 1980 | month = July | pmid = 7395525 | doi = | url = }}</ref>
In [[receptor (biochemistry)|receptor]] [[binding (molecular)|binding]] assays, amitripylinoxide was found to have generally equivalent [[pharmacology]] to amitriptyline, acting as a [[serotonin reuptake inhibitor|serotonin]] and [[norepinephrine reuptake inhibitor]], [[serotonin receptor antagonist]], and [[H1 receptor antagonist|H<sub>1</sub> receptor antagonist]], among other properties, but with approximately 60-fold lower [[affinity (pharmacology)|affinity]] for the [[alpha-adrenergic receptor|α<sub>1</sub>-adrenergic receptor]], and the weakest affinity of any of the TCAs analyzed for the [[muscarinic acetylcholine receptor]]s.<ref name="pmid">{{cite journal | author = Borbe HO, Zierenberg O | title = Amitriptylinoxide: receptor-binding profile compared with other antidepressant drugs | journal = Pharmacopsychiatry | volume = 18 | issue = 5 | pages = 314–9 | year = 1985 | month = September | pmid = | doi = | url = }}</ref><ref name="pmid6185962">{{cite journal | author = Maj J, Vetulani J, Michaluk J, Rogóz Z, Skuza G | title = Central action of amitriptyline N-oxide | journal = Pharmacopsychiatria | volume = 15 | issue = 6 | pages = 187–91 | year = 1982 | month = November | pmid = 6185962 | doi = | url = }}</ref><ref name="pmid7395525">{{cite journal | author = Hyttel J, Christensen AV, Fjalland B | title = Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites | journal = Acta Pharmacologica Et Toxicologica | volume = 47 | issue = 1 | pages = 53–7 | year = 1980 | month = July | pmid = 7395525 | doi = | url = }}</ref>

Revision as of 22:56, 12 February 2010

Amitriptylinoxide
Clinical data
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
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.119.550 Edit this at Wikidata
Chemical and physical data
FormulaC20H23NO
Molar mass293.40 g/mol
3D model (JSmol)
  • [O-][N+](C)(C)CC/C=C2/c1c(cccc1)CCc3c2cccc3

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

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. {{cite book}}: More than one of |pages= and |page= specified (help)
  2. ^ a b Rapp W (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. PMID 360779. {{cite journal}}: Unknown parameter |month= ignored (help)
  3. ^ a b c d Tegeler J, Klieser E, Lehmann E, Heinrich K (1990). "Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline". Pharmacopsychiatry. 23 (1): 45–9. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) Cite error: The named reference "pmid" was defined multiple times with different content (see the help page).
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. {{cite book}}: More than one of |pages= and |page= specified (help)
  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 (1982). "Central action of amitriptyline N-oxide". Pharmacopsychiatria. 15 (6): 187–91. PMID 6185962. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. ^ Hyttel J, Christensen AV, Fjalland B (1980). "Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites". Acta Pharmacologica Et Toxicologica. 47 (1): 53–7. PMID 7395525. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)



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