Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H17BrN2.2ClH |
Molecular Weight | 390.145 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.CN(C)C\C=C(\C1=CC=C(Br)C=C1)C2=CN=CC=C2
InChI
InChIKey=CXGURXWCQYHDIR-ULPVBNQHSA-N
InChI=1S/C16H17BrN2.2ClH/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/b16-9-;;
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 |
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[Adverse effects and zimelidine therapy. Headache, muscle pain and liver involvement--a new disease entity in zimelidine therapy]. | 1983 Jan 5 |
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Acute effects of maprotiline, doxepin and zimeldine with alcohol in healthy volunteers. | 1988 Jan-Feb |
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The specificity of the zimelidine reaction. | 1989 Jan |
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Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells. | 2007 Mar |
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Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2950994
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7776439
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.
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305352
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ACTIVE MOIETY
SUBSTANCE RECORD