Zimelidine

Zimelidine
Systematic (IUPAC) name
3-(4-bromophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine
Clinical data
Pregnancy cat.  ?
Legal status Rx Only, Withdrawn worldwide
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half-life 8.4 +/- 2.0 hours (parent compound)
19.4 +/- 3.6 hours (norzimelidine)
Excretion  ?
Identifiers
CAS number 56775-88-3 YesY 60525-15-7 (anhydrous dihydrochloride), 61129-30-4 (dihydrochloride monohydrate)
ATC code N06AB02
PubChem CID 5365247
DrugBank DB04832
ChemSpider 4517305 YesY
UNII 3J928617DW N
ChEMBL CHEMBL37744 YesY
Chemical data
Formula C16H17BrN2 
Mol. mass 317.224
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Zimelidine (Zimeldine, Normud, Zelmid) was the first selective serotonin reuptake inhibitor (SSRI) antidepressant to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants.

Zimelidine was developed in the early 1980s by Arvid Carlsson, who was then working for the Swedish company Astra AB. It was discovered following a search for drugs with structures similar to brompheniramine (it is a derivative of brompheniramine), an antihistamine with antidepressant activity. Zimelidine was first sold in 1982.

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.

Contents

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.[1] Zimelidine was able to improve cataplexy without causing daytime sleepiness.[2]

Side effects

Most often reported were:

Interactions

  • MAO inhibitors - severe or life-threatening reactions possible

Dosage

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

See also

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. doi:10.2165/00003088-198308060-00004. 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. doi:10.1097/00002826-198602000-00004. PMID 2950994. 
  3. ^ see Godbout et al. 1986



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