Details
Stereochemistry | RACEMIC |
Molecular Formula | C3H2ClF5O |
Molecular Weight | 184.492 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC(F)OC(F)(F)C(F)Cl
InChI
InChIKey=JPGQOUSTVILISH-UHFFFAOYSA-N
InChI=1S/C3H2ClF5O/c4-1(5)3(8,9)10-2(6)7/h1-2H
Molecular Formula | C3H2ClF5O |
Molecular Weight | 184.492 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Enflurane (2-chloro-1,1,2,-trifluoroethyl-difluoromethyl ether) is a halogenated ether structural isomer of isoflurane. Developed by Ross Terrell in 1963, it was first used clinically in 1966. It was increasingly used for inhalational anesthesia during the 1970s and 1980s but is no longer in common use. Clinically, enflurane produces a dose-related depression of myocardial contractility with an associated decrease in myocardial oxygen consumption. Between 2% and 5% of the inhaled dose is oxidized in the liver, producing fluoride ions and difluoromethoxy-difluoroacetic acid. This is significantly higher than the metabolism of its structural isomer isoflurane. The exact mechanism of the action of general anesthetics has not been delineated. Enflurane acts as a positive allosteric modulator of the GABAA, glycine, and 5-HT3 receptors, and as a negative allosteric modulator of the AMPA, kainate, and NMDA receptors, as well as of nicotinic acetylcholine receptors.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3392921 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16973644 |
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Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681790 |
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Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681790 |
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Target ID: CHEMBL2109241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681790 |
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Target ID: CHEMBL2094107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16973644 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ETHRANE Approved UseINDICATIONS AND USAGE. ĒTHRANE (enflurane, USP) may be used for induction and maintenance of general anesthesia. Enflurane may be used to provide analgesia for vaginal delivery. Low concentrations of enflurane (see DOSAGE AND ADMINISTRATION) may also be used to supplement other general anesthetic agents during delivery by Cesarean section. Higher concentrations of enflurane may produce uterine relaxation and an increase in uterine bleeding. Launch Date8.3808002E10 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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15 μg/mL |
2 % single, respiratory dose: 2 % route of administration: Respiratory experiment type: SINGLE co-administered: |
ENFLURANE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60 min |
2 % single, respiratory dose: 2 % route of administration: Respiratory experiment type: SINGLE co-administered: |
ENFLURANE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
4 % single, respiratory |
unhealthy, 25 years n = 1 Health Status: unhealthy Condition: cholecystitis Age Group: 25 years Sex: F Population Size: 1 Sources: |
Disc. AE: Malignant hyperthermia... AEs leading to discontinuation/dose reduction: Malignant hyperthermia Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Malignant hyperthermia | Disc. AE | 4 % single, respiratory |
unhealthy, 25 years n = 1 Health Status: unhealthy Condition: cholecystitis Age Group: 25 years Sex: F Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
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The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations. | 2000 Feb |
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Glycine and gamma-aminobutyric acid(A) receptor function is enhanced by inhaled drugs of abuse. | 2000 Jun |
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Differential effects of general anesthetics on G protein-coupled inwardly rectifying and other potassium channels. | 2001 Jul |
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Comparison of volatile anesthetic actions on intracellular calcium stores of vascular smooth muscle: investigation in isolated systemic resistance arteries. | 2001 May |
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[Biological monitoring of occupational exposure to sevoflurane]. | 2001 May-Jun |
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Myristate, a 14-carbon fatty acid, effectively reverses anesthesia. | 2002 Aug |
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Fresh gas flow is not the only determinant of volatile agent consumption: a multi-centre study of low-flow anaesthesia. | 2002 Jan |
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Pre- and postsynaptic volatile anaesthetic actions on glycinergic transmission to spinal cord motor neurons. | 2002 Jul |
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The variable effect of low-dose volatile anaesthetics on the acute ventilatory response to hypoxia in humans: a quantitative review. | 2002 Jul |
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[Calibration of a room air gas monitor with certified reference gases]. | 2003 Dec |
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Fluoride metabolism in smokers and non-smokers following enflurane anaesthesia. | 2003 Dec |
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The pharmacokinetics of the interstitial space in humans. | 2003 Jul 30 |
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[Effects of enflurane on myocardial reperfusion injury during cardiac surgery with cardiopulmonary bypass]. | 2003 Jun |
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Halogenated inhalational anaesthetics. | 2003 Mar |
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Carbon monoxide production from sevoflurane breakdown: modeling of exposures under clinical conditions. | 2003 Mar |
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Evaluation of the mass spectrometric patterns of volatile liquid anaesthetics to predict the temperature--metal caused decomposition pathway. | 2003 Mar 17 |
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An isothermal titration calorimetry study on the binding of four volatile general anesthetics to the hydrophobic core of a four-alpha-helix bundle protein. | 2003 Nov |
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Mutational analysis of molecular requirements for the actions of general anaesthetics at the gamma-aminobutyric acidA receptor subtype, alpha1beta2gamma2. | 2003 Nov 12 |
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Amino acids in transmembrane domain two influence anesthetic enhancement of serotonin-3A receptor function. | 2003 Oct 21 |
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Volatile anaesthetics induce biochemical alterations in the heme pathway in a B-lymphocyte cell line established from hepatoerythropoietic porphyria patients (LBHEP) and in mice inoculated with LBHEP cells. | 2004 Feb |
Patents
Sample Use Guides
Surgical levels of anesthesia may be maintained with 0.5 to 3.0% enflurane. Maintenance concentrations should not exceed 3.0%. If added relaxation is required, supplemental doses of muscle relaxants may be used. Ventilation to maintain the tension of carbon dioxide in arterial blood in the 35 to 45 mm Hg range is preferred. Hyperventilation should be avoided in order to minimize possible CNS excitation.
Route of Administration:
Respiratory
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681790
Effects of enflurane on NMDA, AMPA, and kainate-gated currents were examined in Xenopus laevis oocytes expressing mouse or human brain mRNA. Enflurane effects on the NMDA, kainate, or AMPA currents were obtained by a preincubation of enflurane alone for 60 s before a coapplication of various drugs and enflurane. Enflurane, at a clinically relevant concentration (1.8 mM), significantly inhibited both maximal and least measurable NMDA, kainate, and AMPA receptor-gated currents.
Substance Class |
Chemical
Created
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admin
on
Edited
Thu Jul 06 00:49:10 UTC 2023
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on
Thu Jul 06 00:49:10 UTC 2023
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Record UNII |
91I69L5AY5
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175975
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WHO-VATC |
QN01AB04
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WHO-ATC |
N01AB04
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LIVERTOX |
NBK548474
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NDF-RT |
N0000175681
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NCI_THESAURUS |
C245
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132998-91-5
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CHEMBL1257
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SUB06530MIG
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3920
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ENFLURANE
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1009
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DB00228
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91I69L5AY5
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4792
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Enflurane
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M4905
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3226
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C47511
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |