Zimelidine

Zimelidine
Zimelidine.svg
Clinical data
Trade namesZelmid
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • Withdrawn worldwide
Pharmacokinetic data
Elimination half-life8.4±2 hours (parent compound)
19.4±3.6 hours (norzimelidine)
Identifiers
  • (Z)-3-(4-Bromophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine
CAS Number
  • 56775-88-3 ☒N 60525-15-7 (anhydrous dihydrochloride), 61129-30-4 (dihydrochloride monohydrate)
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H17BrN2
Molar mass317.230 g·mol−1
3D model (JSmol)
  • Brc2ccc(C(=C/CN(C)C)/c1cccnc1)cc2
  • InChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3/b16-9- checkY
  • Key:OYPPVKRFBIWMSX-SXGWCWSVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

Zimelidine was developed in the late 1970s and 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.

While zimelidine had a very favorable safety profile, within a year and a half of its introduction, rare case reports of Guillain–Barré syndrome emerged that appeared to be caused by the drug, prompting its manufacturer to withdraw it from the market. After its withdrawal, 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. Zimelidine was able to improve cataplexy without causing daytime sleepiness.

Side effects

Most often reported were:

Interactions

  • MAO inhibitors — severe or life-threatening reactions possible[medical citation needed]

See also


This page was last updated at 2023-04-05 09:14 UTC. Update now. View original page.

All our content comes from Wikipedia and under the Creative Commons Attribution-ShareAlike License.


Top

If mathematical, chemical, physical and other formulas are not displayed correctly on this page, please useFirefox or Safari