Details
Stereochemistry | RACEMIC |
Molecular Formula | C3H2ClF5O |
Molecular Weight | 184.4924 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C(C(F)(F)OC(F)F)(Cl)F
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 | 184.4924 |
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 |
---|---|---|---|---|
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 relationship of brain catecholamine levels to enflurane requirements among three strains of mice with different anesthetic sensitivities. | 2001 |
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Myristate, a 14-carbon fatty acid, effectively reverses anesthesia. | 2002 Aug |
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Effects of halothane and enflurane anesthesia on sympathetic beta-adrenoreceptor-mediated pulmonary vasodilation in chronically instrumented dogs. | 2002 Aug |
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A second-generation blood substitute (perflubron emulsion) increases the blood solubility of modern volatile anesthetics in vitro. | 2002 Aug |
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PKQuest: measurement of intestinal absorption and first pass metabolism - application to human ethanol pharmacokinetics. | 2002 Aug 15 |
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PKQuest: a general physiologically based pharmacokinetic model. Introduction and application to propranolol. | 2002 Aug 15 |
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An unusual case of driving under the influence of enflurane. | 2002 Aug 28 |
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An assessment of the cerebroprotective potential of volatile anaesthetics using two independent methods in an in vitro model of cerebral ischaemia. | 2002 Dec 27 |
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Combined effect of hypothermia and crystalloid hemodilution on the solubility of volatile anesthetics in human blood. | 2002 Jul |
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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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The effects of drugs used in anaesthesia on platelet membrane receptors and on platelet function. | 2002 Jun |
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The minimum local anesthetic concentration of ropivacaine for caudal analgesia in children. | 2002 Jun |
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Degrees of aversion shown by rats and mice to different concentrations of inhalational anaesthetics. | 2002 Jun 29 |
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Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil. | 2002 May |
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A novel combretastatin A-4 derivative, AC7700, strongly stanches tumour blood flow and inhibits growth of tumours developing in various tissues and organs. | 2002 May 20 |
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Experimental investigation of the behavior of gas phase simulated moving beds. | 2002 May 31 |
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Myocardial protection by anesthetic agents against ischemia-reperfusion injury: an update for anesthesiologists. | 2002 Oct |
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Anesthetic and ethanol effects on spontaneously opening glycine receptor channels. | 2002 Sep |
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Mice with glycine receptor subunit mutations are both sensitive and resistant to volatile anesthetics. | 2002 Sep |
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PKQuest: capillary permeability limitation and plasma protein binding - application to human inulin, dicloxacillin and ceftriaxone pharmacokinetics. | 2002 Sep 26 |
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Effect of isolation stress on anesthetic requirement in mice. | 2003 |
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Comparison of the effects of neuroleptanesthesia and enflurane or sevoflurane anesthesia on neuromuscular blockade by rocuronium. | 2003 |
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Correlation between 5-fluorouracil metabolism and treatment response in two variants of C26 murine colon carcinoma. | 2003 Aug 18 |
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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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Differential interaction of anaesthetics and antiepileptic drugs with neuronal Na+ channels, Ca2+ channels, and GABA(A) receptors. | 2003 Feb |
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General anesthetic actions in vivo strongly attenuated by a point mutation in the GABA(A) receptor beta3 subunit. | 2003 Feb |
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Anaesthetic agents in adult day case surgery. | 2003 Jan |
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Halogenated anesthetics reduce interleukin-1beta-induced cytokine secretion by rat alveolar type II cells in primary culture. | 2003 Jan |
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Enflurane as an internal standard in monitoring halogenated volatile anaesthetics by headspace gas chromatography-mass spectrometry. | 2003 Jan 24 |
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A new method of inhalation anesthesia with nasopharyngeal insufflation in rat experiment. | 2003 Jul |
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Resuscitation from hemorrhagic shock: experimental model comparing normal saline, dextran, and hypertonic saline solutions. | 2003 Jul |
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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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The effects of enflurane, isoflurane, and intravenous anesthetics on rat diaphragmatic function and fatigability. | 2003 Jun |
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Cold and mechanical allodynia in both hindpaws and tail following thoracic spinal cord hemisection in rats: time courses and their correlates. | 2003 Jun 12 |
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Halogenated inhalational anaesthetics. | 2003 Mar |
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Volatile anesthetics regulate pulmonary vascular tension through different potassium channel subtypes in isolated rabbit lungs. | 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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[Drug-induced seizures]. | 2003 Mar 31 |
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Interaction between artificial membranes and enflurane, a general volatile anesthetic: DPPC-enflurane interaction. | 2003 May |
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Enflurane decreases glutamate neurotransmission to spinal cord motor neurons by both pre- and postsynaptic actions. | 2003 May |
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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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Microvascular mechanisms by which the combretastatin A-4 derivative AC7700 (AVE8062) induces tumour blood flow stasis. | 2003 Oct 6 |
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The actions of sevoflurane and desflurane on the gamma-aminobutyric acid receptor type A: effects of TM2 mutations in the alpha and beta subunits. | 2003 Sep |
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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
by
admin
on
Edited
Fri Jun 25 20:55:03 UTC 2021
by
admin
on
Fri Jun 25 20:55:03 UTC 2021
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Record UNII |
91I69L5AY5
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175975
Created by
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WHO-VATC |
QN01AB04
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WHO-ATC |
N01AB04
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LIVERTOX |
349
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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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1235809
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1009
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3015
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7909
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237-553-4
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7175
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DB00228
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91I69L5AY5
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13838-16-9
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Enflurane
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M4905
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3226
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D004737
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13838-16-9
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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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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |