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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
Structure of ENFLURANE

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

HIDE SMILES / InChI

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.

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

8.3808002E10
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
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

AEs

AESignificanceDosePopulation
Malignant hyperthermia Disc. AE
4 % single, respiratory
Dose: 4 %
Route: respiratory
Route: single
Dose: 4 %
Sources:
unhealthy, 25 years
n = 1
Health Status: unhealthy
Condition: cholecystitis
Age Group: 25 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations.
2000 Feb
Glycine and gamma-aminobutyric acid(A) receptor function is enhanced by inhaled drugs of abuse.
2000 Jun
Differential effects of general anesthetics on G protein-coupled inwardly rectifying and other potassium channels.
2001 Jul
Comparison of volatile anesthetic actions on intracellular calcium stores of vascular smooth muscle: investigation in isolated systemic resistance arteries.
2001 May
[Biological monitoring of occupational exposure to sevoflurane].
2001 May-Jun
Myristate, a 14-carbon fatty acid, effectively reverses anesthesia.
2002 Aug
Fresh gas flow is not the only determinant of volatile agent consumption: a multi-centre study of low-flow anaesthesia.
2002 Jan
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
[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
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
Halogenated inhalational anaesthetics.
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
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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:49:10 UTC 2023
Edited
by admin
on Thu Jul 06 00:49:10 UTC 2023
Record UNII
91I69L5AY5
Record Status Validated (UNII)
Record Version
  • Download
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
ENFLURANE [USP IMPURITY]
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 [GREEN BOOK]
Common Name English
OHIO 347
Common Name English
ENFLURANE [USAN]
Common Name English
ALYRANE
Brand Name English
Enflurane [WHO-DD]
Common Name English
347
Code English
ENFLURANE [JAN]
Common Name 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 Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
WHO-VATC QN01AB04
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
WHO-ATC N01AB04
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
LIVERTOX NBK548474
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
NDF-RT N0000175681
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
NCI_THESAURUS C245
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
Code System Code Type Description
CAS
132998-91-5
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
SUPERSEDED
ChEMBL
CHEMBL1257
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
EVMPD
SUB06530MIG
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
RXCUI
3920
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
ENFLURANE
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
DRUG CENTRAL
1009
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
INN
3015
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
HSDB
7909
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
NSC
115944
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
237-553-4
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
SMS_ID
100000092563
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
IUPHAR
7175
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
DRUG BANK
DB00228
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
FDA UNII
91I69L5AY5
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
CAS
13838-16-9
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
CHEBI
4792
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
LACTMED
Enflurane
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
MERCK INDEX
M4905
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY Merck Index
PUBCHEM
3226
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
RS_ITEM_NUM
1235809
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
MESH
D004737
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID1020562
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
NCI_THESAURUS
C47511
Created by admin on Thu Jul 06 00:49:10 UTC 2023 , Edited by admin on Thu Jul 06 00:49:10 UTC 2023
PRIMARY
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TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
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