Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H17BrN2.2ClH.H2O |
| Molecular Weight | 408.161 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.Cl.CN(C)C\C=C(\C1=CC=C(Br)C=C1)C2=CN=CC=C2
InChI
InChIKey=WFUAVXYXJOQWAZ-GVKRCPFFSA-N
InChI=1S/C16H17BrN2.2ClH.H2O/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;2*1H;1H2/b16-9-;;;
| 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 |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cardiovascular effects of amitriptyline, mianserin and zimelidine in depressed patients. | 1980 |
|
| Event recording in a clinical trial of a new medicine. | 1980 May 3 |
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| Chronic treatment with antidepressants: protentiation of clonidine-induced aggression in mice via noradrenergic mechanism. | 1981 |
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| An open trial of zimelidine in patients with endogenous depression. | 1982 |
|
| Severe headache and disturbed liver function during treatment with zimelidine. | 1982 Nov 13 |
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| Severe headache and disturbed liver function during treatment with zimelidine. | 1982 Oct 9 |
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| A double-blind, controlled evaluation of zimeldine, imipramine and placebo in patients with primary affective disorders. | 1983 |
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| Comparison between zimeldine and amitriptyline of efficacy and adverse symptoms--a combined analysis of four British clinical trials in depression. | 1983 |
|
| [Adverse effects and zimelidine therapy. Headache, muscle pain and liver involvement--a new disease entity in zimelidine therapy]. | 1983 Jan 5 |
|
| Comparison of the (pro)convulsive properties of fluvoxamine and clovoxamine with eight other antidepressants in an animal model. | 1984 |
|
| Increased adult behavioral 'despair' in rats neonatally exposed to desipramine or zimeldine: an animal model of depression? | 1987 Nov |
|
| Acute effects of maprotiline, doxepin and zimeldine with alcohol in healthy volunteers. | 1988 Jan-Feb |
|
| The specificity of the zimelidine reaction. | 1989 Jan |
|
| A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
| Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities. | 2005 Sep 28 |
|
| Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis. | 2011 Oct |
|
| Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
|
| 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 |
Sample Use Guides
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
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
Edited
Fri Dec 15 15:23:42 GMT 2023
by
admin
on
Fri Dec 15 15:23:42 GMT 2023
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| Record UNII |
2T97D1P85R
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| Record Status |
Validated (UNII)
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| Record Version |
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C94725
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NCI_THESAURUS |
C265
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DTXSID7045815
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100000087904
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O-57
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61129-30-4
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SUB05168MIG
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6420041
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C152955
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DBSALT002851
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2T97D1P85R
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CHEMBL37744
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m11595
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PRIMARY | Merck Index |
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |