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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
Structure of ENFLURANE

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

HIDE SMILES / InChI
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ETHRANE

Approved Use

INDICATIONS 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 Date

83808000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
4 % single, respiratory
Dose: 4 %
Route: respiratory
Route: single
Dose: 4 %
Sources:
unhealthy, 25 years
Health Status: unhealthy
Age Group: 25 years
Sex: F
Sources:
Disc. AE: Malignant hyperthermia...
AEs leading to
discontinuation/dose reduction:
Malignant hyperthermia
Sources:
AEs

AEs

AESignificanceDosePopulation
Malignant hyperthermia Disc. AE
4 % single, respiratory
Dose: 4 %
Route: respiratory
Route: single
Dose: 4 %
Sources:
unhealthy, 25 years
Health Status: unhealthy
Age Group: 25 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
The relationship of brain catecholamine levels to enflurane requirements among three strains of mice with different anesthetic sensitivities.
2001
Myristate, a 14-carbon fatty acid, effectively reverses anesthesia.
2002 Aug
Effects of halothane and enflurane anesthesia on sympathetic beta-adrenoreceptor-mediated pulmonary vasodilation in chronically instrumented dogs.
2002 Aug
PKQuest: measurement of intestinal absorption and first pass metabolism - application to human ethanol pharmacokinetics.
2002 Aug 15
PKQuest: a general physiologically based pharmacokinetic model. Introduction and application to propranolol.
2002 Aug 15
An unusual case of driving under the influence of enflurane.
2002 Aug 28
An assessment of the cerebroprotective potential of volatile anaesthetics using two independent methods in an in vitro model of cerebral ischaemia.
2002 Dec 27
The effects of some porphyrinogenic drugs on the brain cholinergic system.
2002 Feb
[Cerebrospinal fluid shunting: anesthetic particularities].
2002 Feb
[Inhalation anesthesia with halogen-containing anesthetics in children].
2002 Jan-Feb
Combined effect of hypothermia and crystalloid hemodilution on the solubility of volatile anesthetics in human blood.
2002 Jul
Pre- and postsynaptic volatile anaesthetic actions on glycinergic transmission to spinal cord motor neurons.
2002 Jul
The variable effect of low-dose volatile anaesthetics on the acute ventilatory response to hypoxia in humans: a quantitative review.
2002 Jul
The effects of drugs used in anaesthesia on platelet membrane receptors and on platelet function.
2002 Jun
The minimum local anesthetic concentration of ropivacaine for caudal analgesia in children.
2002 Jun
Degrees of aversion shown by rats and mice to different concentrations of inhalational anaesthetics.
2002 Jun 29
Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil.
2002 May
Experimental investigation of the behavior of gas phase simulated moving beds.
2002 May 31
Myocardial protection by anesthetic agents against ischemia-reperfusion injury: an update for anesthesiologists.
2002 Oct
Anesthetic and ethanol effects on spontaneously opening glycine receptor channels.
2002 Sep
Mice with glycine receptor subunit mutations are both sensitive and resistant to volatile anesthetics.
2002 Sep
PKQuest: capillary permeability limitation and plasma protein binding - application to human inulin, dicloxacillin and ceftriaxone pharmacokinetics.
2002 Sep 26
Effect of isolation stress on anesthetic requirement in mice.
2003
Comparison of the effects of neuroleptanesthesia and enflurane or sevoflurane anesthesia on neuromuscular blockade by rocuronium.
2003
Correlation between 5-fluorouracil metabolism and treatment response in two variants of C26 murine colon carcinoma.
2003 Aug 18
[Calibration of a room air gas monitor with certified reference gases].
2003 Dec
Fluoride metabolism in smokers and non-smokers following enflurane anaesthesia.
2003 Dec
Differential interaction of anaesthetics and antiepileptic drugs with neuronal Na+ channels, Ca2+ channels, and GABA(A) receptors.
2003 Feb
Anaesthetic agents in adult day case surgery.
2003 Jan
Enflurane as an internal standard in monitoring halogenated volatile anaesthetics by headspace gas chromatography-mass spectrometry.
2003 Jan 24
A new method of inhalation anesthesia with nasopharyngeal insufflation in rat experiment.
2003 Jul
Resuscitation from hemorrhagic shock: experimental model comparing normal saline, dextran, and hypertonic saline solutions.
2003 Jul
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
[Effects of enflurane on myocardial reperfusion injury during cardiac surgery with cardiopulmonary bypass].
2003 Jun
The effects of enflurane, isoflurane, and intravenous anesthetics on rat diaphragmatic function and fatigability.
2003 Jun
Cold and mechanical allodynia in both hindpaws and tail following thoracic spinal cord hemisection in rats: time courses and their correlates.
2003 Jun 12
Halogenated inhalational anaesthetics.
2003 Mar
Volatile anesthetics regulate pulmonary vascular tension through different potassium channel subtypes in isolated rabbit lungs.
2003 Mar
Carbon monoxide production from sevoflurane breakdown: modeling of exposures under clinical conditions.
2003 Mar
Evaluation of the mass spectrometric patterns of volatile liquid anaesthetics to predict the temperature--metal caused decomposition pathway.
2003 Mar 17
The use of a physiologically based pharmacokinetic model to evaluate deconvolution measurements of systemic absorption.
2003 Mar 19
[Drug-induced seizures].
2003 Mar 31
Interaction between artificial membranes and enflurane, a general volatile anesthetic: DPPC-enflurane interaction.
2003 May
Enflurane decreases glutamate neurotransmission to spinal cord motor neurons by both pre- and postsynaptic actions.
2003 May
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
Mutational analysis of molecular requirements for the actions of general anaesthetics at the gamma-aminobutyric acidA receptor subtype, alpha1beta2gamma2.
2003 Nov 12
Amino acids in transmembrane domain two influence anesthetic enhancement of serotonin-3A receptor function.
2003 Oct 21
Microvascular mechanisms by which the combretastatin A-4 derivative AC7700 (AVE8062) induces tumour blood flow stasis.
2003 Oct 6
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
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

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
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.
Name Type Language
ENFLURANE
GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
ENFLURANE [ORANGE BOOK]
Common Name English
NSC-115944
Code English
COMPOUND 347
Common Name English
ENFLURANE [INN]
Common Name English
ENFLURANE [VANDF]
Common Name English
ENFLURANE [MI]
Common Name English
ETHER, 2-CHLORO-1,1,2-TRIFLUOROETHYL DIFLUOROMETHYL
Systematic Name English
ANESTHETIC COMPOUND NO. 347
Code English
ENFLURANE [MART.]
Common Name English
ETHRANE
Brand Name English
ENFLURANE [USP-RS]
Common Name English
(+/-)-2-CHLORO-1,1,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER
Systematic Name English
ETHANE, 2-CHLORO-1-(DIFLUOROMETHOXY)-1,1,2-TRIFLUORO-
Systematic Name English
ENFLURANE [USP]
Common Name English
ENFLURANE [GREEN BOOK]
Common Name English
OHIO 347
Common Name English
ENFLURANE [USAN]
Common Name English
ALYRANE
Brand Name English
347
Code English
ETHANE, 2-CHLORO-1-(DIFLUOROMETHOXY)-1,1,2-TRIFLUORO-, (+/-)-
Systematic Name English
R-E-235CA2
Code English
EFRANE
Brand Name English
ENFLURANE [USP MONOGRAPH]
Common Name English
METHYLFLURETHER
Common Name English
2-CHLORO-1-(DIFLUOROMETHOXY)-1,1,2-TRIFLUOROETHANE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175975
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
WHO-VATC QN01AB04
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
WHO-ATC N01AB04
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
LIVERTOX 349
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
NDF-RT N0000175681
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
Code System Code Type Description
CAS
132998-91-5
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
SUPERSEDED
ChEMBL
CHEMBL1257
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
EVMPD
SUB06530MIG
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
RXCUI
3920
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
ENFLURANE
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
USP_CATALOG
1235809
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
1009
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
INN
3015
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
HSDB
7909
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
ECHA (EC/EINECS)
237-553-4
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
IUPHAR
7175
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
DRUG BANK
DB00228
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
FDA UNII
91I69L5AY5
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
CAS
13838-16-9
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
LACTMED
Enflurane
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
MERCK INDEX
M4905
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY Merck Index
PUBCHEM
3226
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
MESH
D004737
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
EPA CompTox
13838-16-9
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY
NCI_THESAURUS
C47511
Created by admin on Fri Jun 25 20:55:03 UTC 2021 , Edited by admin on Fri Jun 25 20:55:03 UTC 2021
PRIMARY