Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H23Cl2N3O |
Molecular Weight | 404.333 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN(CCC)C(=O)CC1=C(N=C2C=CC(Cl)=CN12)C3=CC=C(Cl)C=C3
InChI
InChIKey=JRTIDHTUMYMPRU-UHFFFAOYSA-N
InChI=1S/C21H23Cl2N3O/c1-3-11-25(12-4-2)20(27)13-18-21(15-5-7-16(22)8-6-15)24-19-10-9-17(23)14-26(18)19/h5-10,14H,3-4,11-13H2,1-2H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22981367
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22981367
Alpidem is an imidazopyridine anxiolytic acting as a partial agonist at γ-aminobutyric acid A (GABA(A)) receptor. Alpidem is selective for GABAA receptors bearing α1 subunits. Alpidem was briefly marketed for the treatment of anxiety, but was withdrawn because of liver toxicity.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22981367 |
1.67 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ANANXYL Approved UseAlpidem was used in the treatment of various anxiety syndromes |
PubMed
Title | Date | PubMed |
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Effects of single doses of alpidem, lorazepam, and placebo on memory and attention in healthy young and elderly volunteers. | 1990 May |
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Repeated treatment with alpidem, a new anxiolytic, does not induce tolerance or physical dependence. | 1993 Sep |
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[Hepatitis induced by alpidem (Ananxyl). Four cases, one of them fatal]. | 1994 |
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[Subfulminant hepatitis caused by alpidem and treated by liver transplantation]. | 1995 Feb |
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2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands. | 2001 Oct |
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Zolpidem, a clinical hypnotic that affects electronic transfer, alters synaptic activity through potential GABA receptors in the nervous system without significant free radical generation. | 2009 Jan-Mar |
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General and efficient copper-catalyzed three-component coupling reaction towards imidazoheterocycles: one-pot synthesis of alpidem and zolpidem. | 2010 Apr 1 |
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Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease. | 2012 Oct |
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Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22981367
The anxiolytic dose range: 75–150 mg administered in two or three daily doses - i.e., single doses of 25–75 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11602696
At 250 to 500 microM, alpidem prevented calcium-induced mitochondrial permeability transition (MPT) in isolated mitochondria, but caused severe glutathione depletion in hepatocytes that was increased by 3-methylcholanthrene, a cytochrome P4501A inducer, and decreased by cystine, a glutathione precursor. Although cell calcium increased, mitochondrial cytochrome c did not translocate to the cytosol and cells died of necrosis. Cell death was prevented by cystine, but not cyclosporin A, an MPT inhibitor. At low concentrations (25-50 microM), in contrast, alpidem accelerated calcium-induced MPT in mitochondria. It did not deplete glutathione in hepatocytes, but nevertheless caused some cell death that was prevented by cyclosporin A, but not by cystine. Alpidem (10 microM) also increased the toxicity of tumor necrosis factor-alpha (1 ng/ml) in hepatocytes. In conclusion, low concentrations of alpidem increase both calcium-induced MPT in mitochondria, and TNF-alpha toxicity in cells, like other PBR ligands.
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C29756
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C80669
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ACTIVE MOIETY