Butriptyline
Clinical data | |
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Trade names | Evadyne, others |
Other names | AY-62014[1] |
Routes of administration | Oral |
ATC code | |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Bioavailability | ?[3] |
Protein binding | >90%[3] |
Metabolism | Hepatic (N-demethylation) |
Metabolites | Norbutriptyline[3] |
Elimination half-life | 20 hours[3] |
Identifiers | |
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JSmol) | |
Chirality | Racemic mixture |
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Butriptyline, sold under the brand name Evadyne among others, is a tricyclic antidepressant (TCA) that has been used in the United Kingdom and several other European countries for the treatment of depression but appears to no longer be marketed.[1][4][5][6][7] Along with trimipramine, iprindole, and amoxapine, it has been described as an "atypical" or "second-generation" TCA due to its relatively late introduction and atypical pharmacology.[8][9] It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.[10]
Medical uses
Butriptyline was used in the treatment of depression.[11] It was usually used at dosages of 150–300 mg/day.[12]
Side effects
Butriptyline is closely related to amitriptyline, and produces similar effects as other TCAs, but its side effects like sedation are said to be reduced in severity and it has a lower risk of interactions with other medications.[6][7][10]
Butriptyline has potent
]Overdose
Pharmacology
Pharmacodynamics
Site | Ki (nM) | Species | Ref |
---|---|---|---|
SERT | 1,360 4,300 10,000 ( IC50 ) |
Human Rat Rat |
[16] [18] [19] |
NET | 5,100 990 1,700 (IC50) |
Human Rat Rat |
[16] [18] [19] |
DAT | 3,940 2,800 5,200 (IC50) |
Human Rat Rat |
[16] [18] [19] |
5-HT1A | 7,000 | Human | [20] |
5-HT2A | 380 | Human | [20] |
5-HT2C | ND | ND | ND |
α1 | 570 | Human | [15] |
α2 | 4,800 | Human | [15] |
D2 |
ND | ND | ND |
H1 | 1.1 | Human | [15] |
mACh | 35 | Human | [15] |
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site. |
In vitro, butriptyline is a strong antihistamine and anticholinergic, moderate 5-HT2 and α1-adrenergic receptor antagonist, and very weak or negligible monoamine reuptake inhibitor.[15][20][16][19] These actions appear to confer a profile similar to that of iprindole and trimipramine with serotonin-blocking effects as the apparent predominant mediator of mood-lifting efficacy.[21][19][18]
However, in small clinical trials, using similar doses, butriptyline was found to be similarly effective to amitriptyline and imipramine as an antidepressant, despite the fact that both of these TCAs are far stronger as both 5-HT2 antagonists and serotonin–norepinephrine reuptake inhibitors.[15][20][22] As a result, it may be that butriptyline has a different mechanism of action, or perhaps functions as a prodrug in the body to a metabolite with different pharmacodynamics.
Pharmacokinetics
Therapeutic concentrations of butriptyline are in the range of 60–280 ng/mL (204–954 nmol/L).[23] Its plasma protein binding is greater than 90%.[3]
Chemistry
Butriptyline is a
History
Butriptyline was developed by Wyeth and introduced in the United Kingdom in either 1974 or 1975.[5][30][31]
Society and culture
Generic names
Butriptyline is the
Brand names
Butriptyline has been marketed under the brand names Evadene, Evadyne, Evasidol, and Centrolese.[1][4][5]
Availability
Butriptyline has been marketed in Europe, including in the United Kingdom, Belgium, Luxembourg, Austria, and Italy.[4][5]
References
- ^ ISBN 978-1-4757-2085-3.
- ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
- ^ ISBN 978-3-527-64565-7.
- ^ ISBN 3-88763-075-0.
- ^ ISBN 978-0-8155-1856-3.
- ^ ]
- ^ ISBN 978-0-89862-674-2.
- ISBN 978-81-312-1158-8.
- ISBN 978-81-8147-009-6.
- ^ ISBN 978-0-444-53266-4.
- ^ ISBN 978-94-011-4439-1.
- ISBN 978-0-521-28438-7.
- ^ PMID 17471183.
- ^ ISBN 978-3-7186-5027-9.
- ^ PMID 6086881.
- ^ PMID 9537821.
- ^ Roth BL, Driscol J. "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 14 August 2017.
- ^ PMID 6499924.
- ^ S2CID 8183053.
- ^ PMID 3816971.
- PMID 166748.
- ISBN 978-1-4831-9193-5.
- ISBN 978-3-642-73058-0.
- ^ ISBN 978-94-007-5805-6.
- ISBN 978-1-60913-345-0.
- ISBN 978-0-471-95052-3.
- ISBN 978-3-527-64632-6.
- ISBN 1-56053-470-2.
- ISBN 978-0-19-162675-3.
- ISBN 978-1-4899-3436-9.
- ISBN 978-0-7817-2845-4.