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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

1972
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 relationship of brain catecholamine levels to enflurane requirements among three strains of mice with different anesthetic sensitivities.
2001
Volatile general anesthetics reveal a neurobiological role for the white and brown genes of Drosophila melanogaster.
2001 Dec
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.
2001 Dec
Inhalation anaesthetics increase heart rate by decreasing cardiac vagal activity in dogs.
2001 Nov
[Alcohol-xenobiotic interactions. Role of cytochrome P450 2E1].
2001 Nov
A mouse model for peripheral neuropathy produced by a partial injury of the nerve supplying the tail.
2002 Apr 12
213Bi-PAI2 conjugate selectively induces apoptosis in PC3 metastatic prostate cancer cell line and shows anti-cancer activity in a xenograft animal model.
2002 Apr 8
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
A second-generation blood substitute (perflubron emulsion) increases the blood solubility of modern volatile anesthetics in vitro.
2002 Aug
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
The effects of some porphyrinogenic drugs on the brain cholinergic system.
2002 Feb
[Cerebrospinal fluid shunting: anesthetic particularities].
2002 Feb
Caudal anesthesia reduces the minimum alveolar concentration of enflurane for laryngeal mask airway removal in boys.
2002 Feb
Mitomycin C in combination with radiotherapy as a potent inhibitor of tumour cell repopulation in a human squamous cell carcinoma.
2002 Feb 1
[A study of the feasibility and efficacy of fetal surgical closure of spontaneous cleft lip in CL/fraser mice].
2002 Jan
Predictive performance of a physiological model for enflurane closed-circuit anaesthesia: effects of continuous cardiac output measurements and age-related solubility data.
2002 Jan
Fresh gas flow is not the only determinant of volatile agent consumption: a multi-centre study of low-flow anaesthesia.
2002 Jan
The inhibitory effects of anesthetics and ethanol on substance P receptors expressed in Xenopus oocytes.
2002 Jan
Comparison of Amsorb, sodalime, and Baralyme degradation of volatile anesthetics and formation of carbon monoxide and compound a in swine in vivo.
2002 Jan
Increased lymphatic lipid transport in genetically diabetic obese rats.
2002 Jan
[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
Subcellular localization of trifluoroacetylated liver proteins in association with hepatitis following isoflurane.
2002 Mar
Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil.
2002 May
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
Experimental investigation of the behavior of gas phase simulated moving beds.
2002 May 31
Comparison of the effects of neuroleptanesthesia and enflurane or sevoflurane anesthesia on neuromuscular blockade by rocuronium.
2003
[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
Halogenated anesthetics reduce interleukin-1beta-induced cytokine secretion by rat alveolar type II cells in primary culture.
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
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
[Drug-induced seizures].
2003 Mar 31
Interaction between artificial membranes and enflurane, a general volatile anesthetic: DPPC-enflurane interaction.
2003 May
Mutational analysis of molecular requirements for the actions of general anaesthetics at the gamma-aminobutyric acidA receptor subtype, alpha1beta2gamma2.
2003 Nov 12
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 Fri Dec 15 17:29:39 GMT 2023
Edited
by admin
on Fri Dec 15 17:29:39 GMT 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 Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
WHO-VATC QN01AB04
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
WHO-ATC N01AB04
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
LIVERTOX NBK548474
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
NDF-RT N0000175681
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
Code System Code Type Description
CAS
132998-91-5
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
SUPERSEDED
ChEMBL
CHEMBL1257
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
EVMPD
SUB06530MIG
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
RXCUI
3920
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
ENFLURANE
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
DRUG CENTRAL
1009
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
INN
3015
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PRIMARY
HSDB
7909
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PRIMARY
NSC
115944
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
237-553-4
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
SMS_ID
100000092563
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
IUPHAR
7175
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
DRUG BANK
DB00228
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
FDA UNII
91I69L5AY5
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
CAS
13838-16-9
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
CHEBI
4792
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
LACTMED
Enflurane
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
MERCK INDEX
m4905
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY Merck Index
PUBCHEM
3226
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
RS_ITEM_NUM
1235809
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
MESH
D004737
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID1020562
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
NCI_THESAURUS
C47511
Created by admin on Fri Dec 15 17:29:39 GMT 2023 , Edited by admin on Fri Dec 15 17:29:39 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
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METABOLITE -> PARENT
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ACTIVE MOIETY