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

Molecular Formula	C16H17BrN2
Molecular Weight	317.224
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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Cataplexy 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2950994	Primary	Withdrawn	zimeldine Approved Use Unknown Launch Date 3.78691191E11
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6230889	Primary	Withdrawn	zimeldine Approved Use Unknown Launch Date 3.78691191E11
Ethanol consumption 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6328388	Primary	Withdrawn	zimeldine Approved Use Unknown Launch Date 3.78691191E11

PubMed

Title	Date	PubMed
Cardiovascular effects of amitriptyline, mianserin and zimelidine in depressed patients.	1980	6452647
Event recording in a clinical trial of a new medicine.	1980 May 3	6448650
Chronic treatment with antidepressants: protentiation of clonidine-induced aggression in mice via noradrenergic mechanism.	1981	6458665
An open trial of zimelidine in patients with endogenous depression.	1982	6211416
Severe headache and disturbed liver function during treatment with zimelidine.	1982 Nov 13	6215969
Severe headache and disturbed liver function during treatment with zimelidine.	1982 Oct 9	6215083
A double-blind, controlled evaluation of zimeldine, imipramine and placebo in patients with primary affective disorders.	1983	6230897
Comparison between zimeldine and amitriptyline of efficacy and adverse symptoms--a combined analysis of four British clinical trials in depression.	1983	6230896
[Adverse effects and zimelidine therapy. Headache, muscle pain and liver involvement--a new disease entity in zimelidine therapy].	1983 Jan 5	6220186
Comparison of the (pro)convulsive properties of fluvoxamine and clovoxamine with eight other antidepressants in an animal model.	1984	6442931
Increased adult behavioral 'despair' in rats neonatally exposed to desipramine or zimeldine: an animal model of depression?	1987 Nov	2960986
The specificity of the zimelidine reaction.	1989 Jan	2531772
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.	2005 Feb	15342952
Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities.	2005 Sep 28	16125150
Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells.	2007 Mar	17175557
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis.	2011 Oct	21515356
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014 Jan	24085192

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:16:18 UTC 2023` Edited by `admin` on `Fri Dec 15 17:16:18 UTC 2023`
Record UNII	3J928617DW
Record Status	`Validated (UNII)`
Record Version

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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