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 countries for the treatment of depression but appears to no longer be marketed. 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. It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.
Medical uses
Butriptyline was used in the treatment of depression.
It was usually used at dosages of 150–300 mg/day.
Side effects
Butriptyline is closely related to
amitriptyline, and produces similar effects as other TCAs, but its
like
sedation are said to be reduced in severity and it has a lower risk of
drug interaction with other medications.
Butriptyline has potent antihistamine effects, resulting in sedation and somnolence. It also has potent anticholinergic effects, resulting in side effects like dry mouth, constipation, urinary retention, blurred vision, and cognitive/memory impairment. The drug has relatively weak effects as an alpha-1 blocker and has no effects as a norepinephrine reuptake inhibitor, so is associated with little to no antiadrenergic and adrenergic side effects.
Overdose
Pharmacology
Pharmacodynamics
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| 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. 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.
However, in small , 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. 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).
Its plasma protein binding is greater than 90%.
Chemistry
Butriptyline is a tricyclic compound, specifically a dibenzocycloheptadiene, and possesses three rings fused together with a
side chain attached in its chemical structure.
Other dibenzocycloheptadiene TCAs include
amitriptyline,
nortriptyline, and
protriptyline.
Butriptyline is an analogue of amitriptyline with an
isobutyl side chain instead of a side chain.
It is a
tertiary amine TCA, with its
side chain-
demethylation metabolite norbutriptyline being a
secondary amine.
Other tertiary amine TCAs include
amitriptyline,
imipramine,
clomipramine,
dosulepin (dothiepin),
doxepin, and
trimipramine.
The
chemical name of butriptyline is 3-(10,11-dihydro-5
H-dibenzo
a,
dcycloheptene-5-yl)-
N,
N,2-trimethylpropan-1-amine and its
free base form has a
chemical formula of C
21H
27N with a
molecular weight of 293.446 g/mol.
The drug has been used commercially both as the free base and as the
hydrochloride salt.
The CAS Registry Number of the free base is 15686-37-0 and of the hydrochloride is 5585-73-9.
History
Butriptyline was developed by
Wyeth and introduced in the
United Kingdom in either 1974 or 1975.
Society and culture
Generic names
Butriptyline is the
English language and
French language generic term of the drug and its , , and , while
butriptyline hydrochloride is its and .
Its generic name in
Latin language is
butriptylinum, in
German language is
butriptylin, and in
Spanish language is
butriptylina.
Brand names
Butriptyline has been marketed under the brand names
Evadene,
Evadyne,
Evasidol, and
Centrolese.
Availability
Butriptyline has been marketed in
Europe, including in the
United Kingdom,
Belgium,
Luxembourg,
Austria, and
Italy.