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Zimelidine

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Zimelidine chemical structure
Zimelidine

3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-yl-prop-2-en-1-amine
IUPAC name
CAS number
56775-88-3
ATC code

N06AB02

PubChem
41987
DrugBank
[1]
Chemical formula {{{chemical_formula}}}
Molecular weight 317.224
Bioavailability  ?
Metabolism  ?
Elimination half-life 8.4 +/- 2.0 hours (parent compound)
19.4 +/- 3.6 hours (norzimelidine)
Excretion  ?
Pregnancy category  ?
Legal status Withdrawn from market
Routes of administration Oral

Zimelidine (Normud®, Zelmid®) was the first marketed selective serotonin reuptake inhibitor (SSRI) antidepressant. It is a pyridylallylamine, structurally different from other antidepressants. The substance was developed in the early 1980s by the Swedish company AstraZeneca following a search for drugs with structures similar to chlorpheniramine (it is a derivative of brompheniramine), an antihistamine with antidepressant activity. It was then licensed to other drug producers.

Zimelidine has been banned worldwide due to serious, sometimes fatal, cases of central and/or peripheral neuropathy known as Guillain-Barré syndrome and due to a peculiar hypersensitivity reaction involving many organs including skin exanthema, flu-like symptoms, arthralgias, and sometimes eosinophilia. Additionally, zimelidine was charged to cause an increase in suicidal ideation and/or attempts among depressive patients. After its ban, it was succeeded by fluvoxamine and fluoxetine (derived from the antihistamine diphenhydramine) in that order, and the other SSRIs.

Mechanism of action

The mode of action is a strong reuptake inhibition of serotonin from the synaptic cleft. Postsynaptic receptors are not acted upon.

Other uses

Zimelidine was reported by Montplaisir and Godbout to be very effective for cataplexy in 1986, back when this was usually controlled by tricyclic antidepressants, which often had anticholinergic effects.[2] Zimelidine was able to improve cataplexy without causing daytime sleepiness.[3]

Side effects

Most often reported were:

Interactions

Dosage

The former doses were 200 to 400mg daily in outpatients and up to 600mg in inpatients.

References

  1. ^  Caille G, Kouassi E, de Montigny C. (1986). Pharmacokinetic study of zimelidine using a new GLC method. Clinical Pharmacokinetics 8 (6): 530-40. PMID 6228368.
  2. ^  Godbout R, Montplaisir J. (1986). The effect of zimelidine, a serotonin-reuptake blocker, on cataplexy and daytime sleepiness of narcoleptic patients.. Clinical Neuropharmacology 9 (1): 46-51. PMID 2950994.
  3. ^  see Godbout et al. 1986


Antidepressants (ATC N06A) edit
Monoamine oxidase inhibitors (MAOI) Harmaline, Iproclozide, Iproniazid, Isocarboxazid, Nialamide, Phenelzine, Selegiline, Toloxatone, Tranylcypromine
Reversible inhibitor of monoamine oxidase A (RIMA) Brofaromine, Moclobemide
Dopamine reuptake inhibitor (DARI) Amineptine, Phenmetrazine, Vanoxerine, Modafinil
Norepinephrine-dopamine reuptake inhibitors Bupropion
Norepinephrine reuptake inhibitor (NRI) or (NARI) Atomoxetine, Maprotiline, Reboxetine, Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Duloxetine, Milnacipran, Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate, Etoperidone, Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Tricyclic antidepressants (TCA) Amitriptyline, Amoxapine, Butriptyline, Clomipramine, Desipramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Lofepramine, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine
Tetracyclic antidepressants Maprotiline, Mianserin, Nefazodone, Trazodone
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine
fr:zimelidine
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