Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:26:19 UTC |
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Update Date | 2014-12-24 20:25:50 UTC |
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Accession Number | T3D2717 |
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Identification |
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Common Name | Enflurane |
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Class | Small Molecule |
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Description | Enflurane is only found in individuals that have used or taken this drug. It is an extremely stable inhalation anesthetic that allows rapid adjustments of anesthesia depth with little change in pulse or respiratory rate. [PubChem]Enflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Enflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. It also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Enflurane also binds to and angonizes the GABA receptor, the large conductance Ca2+ activated potassium channel, the glycine receptor, and antagonizes the glutamate receptor receptor. These yield a decreased depolarization and therefore, tissue excitability which results in anesthesia. |
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Compound Type | - Anesthetic
- Anesthetic, Inhalation
- Drug
- General Anesthetic
- Lachrymator
- Metabolite
- Organic Compound
- Organochloride
- Organofluoride
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether | Alyrane | Anesthetic 347 | Anesthetic Compound No. 347 | Compound 347 | Efrane | Endurane | Enfluran | Enflurano | Enfluranum | Ethrane | Methylflurether | Ohio 347 |
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Chemical Formula | C3H2ClF5O |
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Average Molecular Mass | 184.492 g/mol |
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Monoisotopic Mass | 183.971 g/mol |
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CAS Registry Number | 13838-16-9 |
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IUPAC Name | 2-chloro-1-(difluoromethoxy)-1,1,2-trifluoroethane |
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Traditional Name | enflurane |
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SMILES | FC(F)OC(F)(F)C(F)Cl |
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InChI Identifier | InChI=1/C3H2ClF5O/c4-1(5)3(8,9)10-2(6)7/h1-2H |
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InChI Key | InChIKey=JPGQOUSTVILISH-UHFFFAOYNA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as organofluorides. Organofluorides are compounds containing a chemical bond between a carbon atom and a fluorine atom. |
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Kingdom | Organic compounds |
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Super Class | Organohalogen compounds |
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Class | Organofluorides |
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Sub Class | Not Available |
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Direct Parent | Organofluorides |
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Alternative Parents | |
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Substituents | - Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organofluoride
- Organochloride
- Alkyl halide
- Alkyl fluoride
- Alkyl chloride
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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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 | - Cytoplasm
- Extracellular
- Membrane
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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 | Liquid |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | 56.5 | Solubility | 5620 mg/L (at 37°C) | LogP | 2.1 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-9700000000-853b1a9a2c5092ed803f | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00ls-9700000000-b8f66e13b2c7ea3b8afd | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01q9-1900000000-16ebf7410f0a86a95b6b | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02u1-5900000000-156ada188e3d7c93066b | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-cda3ea1a89b8c052a64a | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0159-9700000000-eb38bb16c4ca48ce679e | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9400000000-7192f6a2a8627c6763ea | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-1900000000-4d034b914ffdba24bc4d | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0159-3900000000-ffa0ad51b68a798a19ec | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-3900000000-2afb1bd4a0ff78bf685c | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-f72d585725966be19d66 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-1c338b7673c3ce0b0ba6 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03xr-1900000000-39005ff2a0a05b8ee55b | 2021-09-22 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0gb9-9300000000-03817aefdcc06ee54c49 | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Rapidly absorbed into the circulation via the lungs. |
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Mechanism of Toxicity | Enflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Enflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. It also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Enflurane also binds to and angonizes the GABA receptor, the large conductance Ca2+ activated potassium channel, the glycine receptor, and antagonizes the glutamate receptor receptor. These yield a decreased depolarization and therefore, tissue excitability which results in anesthesia. |
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Metabolism | 2.4% of the dose is slowly metabolized hepatically via oxidation and dehalogenation (primarily through the actions of cytochrome P450 2E1). Leads to low levels of serum fluoride (15 µmol/L). |
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Toxicity Values | LD50: 5.4 ml/kg (oral, rat). |
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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 | Used for the induction and maintenance of general anaesthesia during surgery and cesarean section and also used for analgesia during vaginal delivery. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Symptoms of acute overdose include nausea, vomiting, irritation to the eyes, skin and nose/throat, headache, dizziness, and drowsiness. Symptoms of chronic overdose include hypotension, cardiac arrhythmias, respiratory depression, and liver/kidney dysfunction. |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00228 |
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HMDB ID | HMDB14373 |
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PubChem Compound ID | 3226 |
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ChEMBL ID | CHEMBL1257 |
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ChemSpider ID | 3113 |
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KEGG ID | C07516 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 4792 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Enflurane |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Enflurane |
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References |
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Synthesis Reference | Terrell, R.C.; U.S. Patents 3,469,011; September 23,1969 and 3,527,813; September 8,
1970; both assigned to Air Reduction Company, Incorporated. |
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MSDS | Link |
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General References | - Drugs.com [Link]
- Minrad International Inc. (2005). Compound 347: Enflurane, USP Liquid for Inhalation. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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