ZIMELDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H17BrN2
Molecular Weight	317.224
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)C\C=C(\C1=CC=C(Br)C=C1)C2=CN=CC=C2

InChI

InChIKey=OYPPVKRFBIWMSX-SXGWCWSVSA-N

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-

HIDE SMILES / InChI

Description
Sources: Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 21–22, 39–40. ISBN 0-19-515130-5. | https://www.ncbi.nlm.nih.gov/pubmed/3156214 | https://www.drugbank.ca/drugs/DB04832 | https://www.ncbi.nlm.nih.gov/pubmed/26123880

Zimeldine was one of the first selective serotonin reuptake inhibitors to be marketed as an antidepressant under the brand names Zimeldine, Normud, and Zelmid. Zimelidine was developed in the late 1970s and early 1980s by Arvid Carlsson, who was then working for the Swedish company Astra AB. 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 withdrawl from the market.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cataplexy 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2950994	Primary	Withdrawn	zimeldine Approved Use Unknown Launch Date 1981
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6230889	Primary	Withdrawn	zimeldine Approved Use Unknown Launch Date 1981
Ethanol consumption 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6328388	Primary	Withdrawn	zimeldine Approved Use Unknown Launch Date 1981

PubMed

Title	Date	PubMed
An open trial of zimelidine in patients with endogenous depression.	1982	6211416
The specificity of the zimelidine reaction.	1989 Jan	2531772
Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities.	2005 Sep 28	16125150
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis.	2011 Oct	21515356
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.	2013 Dec	24052561

Patents

Sample Use Guides

In Vivo Use Guide

Eleven narcoleptic patients were studied before and one month after treatment with 100 mg daily oral dose of zimelidine. All patients improved with zimelidine. Ten patients had complete suppression of cataplexy.

Route of Administration: Oral

In Vitro Use Guide

Human PC-3, DU-145, and LNCaP cells were each maintained in Leibovitz's L-medium containing 5% fetal bovine serum and antibiotics. Cells were plated in serum-supplemented growth medium at 10,000 cells per well and treated with zimelidine 24 hours later. After 3 days, cell numbers were determined using the MTT assay. Zimelidine demonstrated concentration dependent inhibition against all three prostate carcinoma cell lines. The half maximal concentration for growth inhibition was reported as 15.0, 25.0, and 65.0 micro-M for PC-3, DU-145, and LNCaP respectively.

Name

Type

Language

ZIMELDINE

Official Name

English

(Z)-3-(1-(P-BROMOPHENYL)-3-(DIMETHYLAMINO)PROPENYL)PYRIDINE

Common Name

English

ZIMELDINE [MI]

Common Name

English

ZIMELIDINE

Common Name

English

2-PROPEN-1-AMINE, 3-(4-BROMOPHENYL)-N,N-DIMETHYL-3-(3-PYRIDINYL)-, (Z)-

Systematic Name

English

ZIMELDINE [HSDB]

Common Name

English

zimeldine [INN]

Common Name

English

Zimeldine [WHO-DD]

Common Name

English

CIS-ZIMELIDINE

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN06AB02