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Zimelidine

Catalog No. DB04832 Name DrugBank
CAS Number 56775-88-3 Website http://www.ualberta.ca/
M. F. C16H17BrN2 Telephone (780) 492-3111
M. W. 317.22358 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 4376

SYNONYMS

IUPAC name
[3-(4-bromophenyl)-3-(pyridin-3-yl)prop-2-en-1-yl]dimethylamine
IUPAC Traditional name
zelmid
Synonyms
Cis-zimelidine
(Z)-3-[1-(p-Bromophenyl)-3-(dimethylamino)propenyl]pyridine
Zimeldine
(Z)-3-(4'-Bromophenyl)-3-(3''-pyridyl)dimethylallylamine
(z)-zimelidine

DATABASE IDS

PubChem SID 46504589
PubChem CID 5365247
CAS Number 56775-88-3

PROPERTIES

DETAILS

Description (English)
Item Information
Drug Groups withdrawn
Description 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.
Indication For the treatment of depression.
Pharmacology Zimelidine was the first marketed selective serotonin reuptake inhibitor (SSRI) antidepressant. It is a pyridylallylamine, structurally different from other antidepressants.
Affected Organisms
Humans and other mammals
Half Life 8.4 +/- 2.0 hours for the parent compound and 19.4 +/- 3.6 hours for norzimelidine.
References
Caille G, Kouassi E, de Montigny C: Pharmacokinetic study of zimelidine using a new GLC method. Clin Pharmacokinet. 1983 Nov-Dec;8(6):530-40. [Pubmed]
Godbout R, Montplaisir J: The effect of zimelidine, a serotonin-reuptake blocker, on cataplexy and daytime sleepiness of narcoleptic patients. Clin Neuropharmacol. 1986;9(1):46-51. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Caille G, Kouassi E, de Montigny C: Pharmacokinetic study of zimelidine using a new GLC method. Clin Pharmacokinet. 1983 Nov-Dec;8(6):530-40. Pubmed
  • Godbout R, Montplaisir J: The effect of zimelidine, a serotonin-reuptake blocker, on cataplexy and daytime sleepiness of narcoleptic patients. Clin Neuropharmacol. 1986;9(1):46-51. Pubmed