| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-08-30 21:05:40 UTC |
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| Update Date | 2016-11-09 01:09:09 UTC |
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| Accession Number | CHEM003528 |
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| Identification |
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| Common Name | Ethyl loflazepate |
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| Class | Small Molecule |
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| Description | Ethyl loflazepate (marketed under the brand names Meilax, Ronlax and Victan) is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. In animal studies it was found to have low toxicity, although in rats evidence of pulmonary phospholipidosis occurred with pulmonary foam cells developing with long-term use of very high doses. Its elimination half-life is 51 hours - 103 hours. |
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| Contaminant Sources | - STOFF IDENT Compounds
- T3DB toxins
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| Contaminant Type | - Amide
- Amine
- Drug
- Ester
- Ether
- Organic Compound
- Organochloride
- Organofluoride
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Meilax | Kegg | | Ethyl loflazepic acid | Generator | | Ethyl flucozepate | MeSH | | Victan | MeSH |
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| Chemical Formula | C18H14ClFN2O3 |
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| Average Molecular Mass | 360.767 g/mol |
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| Monoisotopic Mass | 360.068 g/mol |
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| CAS Registry Number | 29177-84-2 |
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| IUPAC Name | ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylate |
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| Traditional Name | ethyl loflazepate |
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| SMILES | CCOC(=O)C1N=C(C2=CC=CC=C2F)C2=C(NC1=O)C=CC(Cl)=C2 |
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| InChI Identifier | InChI=1S/C18H14ClFN2O3/c1-2-25-18(24)16-17(23)21-14-8-7-10(19)9-12(14)15(22-16)11-5-3-4-6-13(11)20/h3-9,16H,2H2,1H3,(H,21,23) |
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| InChI Key | CUCHJCMWNFEYOM-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Alpha amino acid esters |
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| Alternative Parents | |
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| Substituents | - Alpha-amino acid ester
- Benzodiazepine
- 1,4-benzodiazepine
- Fluorobenzene
- Halobenzene
- Aryl chloride
- Aryl fluoride
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- 1,3-dicarbonyl compound
- Carboxamide group
- Carboxylic acid ester
- Secondary carboxylic acid amide
- Ketimine
- Lactam
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Monocarboxylic acid or derivatives
- Imine
- Organooxygen compound
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organofluoride
- Organic oxide
- Organohalogen compound
- Organochloride
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 196°C | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0019000000-709f2c6e1d2bcd811d84 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02t9-1119000000-d25b4aa73f3205570971 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kr-2796000000-9d9a2caec19d41eebb10 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0bt9-1019000000-c8f9c8a13f5c64cb6411 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01p9-3098000000-d705fb6543b8a4e0085d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9121000000-0fb98628eaf5c16bd6fd | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0670-1941000000-427495e16cf17300345d | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. |
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| Metabolism | Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound. Ethyl loflazepate was designed to be a prodrug for descarboxyloflazepate, its active metabolite. It is the active metabolite which is responsible for most of the pharmacological effects rather than ethyl loflazepate. The main metabolites of ethyl loflazepate are descarbethoxyloflazepate, loflazepate and 3-hydroxydescarbethoxyloflazepate.[10] Accumulation of the active metabolites of ethyl loflazepate are not affected by those with renal failure or impairment. (Wikipedia) |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Ethyl loflazepate possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. (Wikipedia) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | The symptoms of an overdose of ethyl loflazepate include sleepiness, agitation and ataxia. Hypotonia may also occur in severe cases. These symptoms occur much more frequently and severely in children.[12] Death from therapeutic maintenance doses of ethyl loflazepate taken for 2 – 3 weeks has been reported in 3 elderly patients. The cause of death was asphyxia due to benzodiazepine toxicity. (Wikipedia) |
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| Treatment | General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended. |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB01545 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Ethyl loflazepate |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 3299 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | British Patent 1,538,165. |
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| MSDS | Not Available |
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| General References | Not Available |
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