U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 ISOFLURANE

SMILES

C(C(F)(F)F)(Cl)OC(F)F

InChI

InChIKey=PIWKPBJCKXDKJR-UHFFFAOYSA-N
InChI=1S/C3H2ClF5O/c4-1(3(7,8)9)10-2(5)6/h1-2H

HIDE SMILES / InChI

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 ( + / - )

Isoflurane (1-chloro-2, 2,2-trifluoroethyl difluoromethyl ether) a nonflammable liquid administered by vaporizing, is a general inhalation anesthetic drug. Isoflurane is a clear, colorless, stable liquid containing no additives or chemical stabilizers. Similar to many general anesthetics, the exact mechanism of the action has not been clearly delineated. Isoflurane reduces pain sensitivity (analgesia) and relaxes muscles. Isoflurane likely potentiates GABA-A and glycine receptor activity, which decreases motor function, inhibits receptor activity in the NMDA glutamate receptor subtypes and binds to glutamate receptors. Isoflurane is always administered in conjunction with air and/or pure oxygen. Often nitrous oxide is also used. Although its physical properties imply that anesthesia can be induced more rapidly than with halothane, its pungency can irritate the respiratory system, negating this theoretical advantage conferred by its physical properties. It is usually used to maintain a state of general anesthesia that has been induced with another drug, such as thiopentone or propofol.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FORANE

Approved Use

INDICATIONS & USAGE Isoflurane may be used for induction and maintenance of general anesthesia. Adequate data have not been developed to establish its application in obstetrical anesthesia.

Launch Date

314323200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
800 μg/mL
180 mg/kg single, intravenous
dose: 180 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ISOFLURANE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.765 μg × min/mL
180 mg/kg single, intravenous
dose: 180 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ISOFLURANE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.01 min
180 mg/kg single, intravenous
dose: 180 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ISOFLURANE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1382.4 % * h multiple, respiratory
Highest studied dose
Dose: 1382.4 % * h
Route: respiratory
Route: multiple
Dose: 1382.4 % * h
Sources:
unhealthy, 25 years
Health Status: unhealthy
Age Group: 25 years
Sex: M
Sources:
1975.2 % * h multiple, respiratory
Highest studied dose
Dose: 1975.2 % * h
Route: respiratory
Route: multiple
Dose: 1975.2 % * h
Sources:
unhealthy, 4 years
Health Status: unhealthy
Age Group: 4 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Desflurane, compared to halothane, augments phenylephrine-induced contraction in isolated rat aorta smooth muscle.
2001 Apr
Neostigmine antagonism of rocuronium block during anesthesia with sevoflurane, isoflurane or propofol.
2001 Apr
Effects of diazepam and flumazenil on minimum alveolar concentrations for dogs anesthetized with isoflurane or a combination of isoflurane and fentanyl.
2001 Apr
Desflurane pharmacokinetics during cardiopulmonary bypass.
2001 Apr
Sevoflurane versus isoflurane in patients undergoing valvular cardiac surgery.
2001 Apr
Effects of chronic exposure to anaesthetic gases on some immune parameters.
2001 Apr 10
[Epileptogenic drugs in anesthesia].
2001 Feb
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].
2001 Feb
[Computer simulation and pharmacoeconomics. Computer simulation as an aid for the analysis of operating room efficiency: an example].
2001 Feb
[Clinical evaluation of roxatidine acetate hydrochlorides as a preanesthetic medication].
2001 Feb
No effect of albinism on sedative-hypnotic sensitivity to ethanol and anesthetics.
2001 Feb
Protective effects of volatile agents against methacholine-induced bronchoconstriction in rats.
2001 Feb
Agent-selective effects of volatile anesthetics on GABAA receptor-mediated synaptic inhibition in hippocampal interneurons.
2001 Feb
Absence of direct antioxidant effects from volatile anesthetics in primary mixed neuronal-glial cultures.
2001 Feb
Cardiovascular effects of sevoflurane, isoflurane, halothane, and fentanyl-midazolam in children with congenital heart disease: an echocardiographic study of myocardial contractility and hemodynamics.
2001 Feb
Desflurane or sevoflurane for gynaecological day-case anaesthesia with spontaneous respiration?
2001 Feb
Clinical evaluation of the Mapleson theoretical ideal fresh gas flow sequence at the start of low-flow anaesthesia with isoflurane, sevoflurane and desflurane.
2001 Feb
CO(2)-controlled sampling of alveolar gas in mechanically ventilated patients.
2001 Feb
Smoking status and body size increase carbon monoxide concentrations in the breathing circuit during low-flow anesthesia.
2001 Feb
Online monitoring of air quality at the postanesthetic care unit by proton-transfer-reaction mass spectrometry.
2001 Feb
The use of esmolol as an alternative to remifentanil during desflurane anesthesia for fast-track outpatient gynecologic laparoscopic surgery.
2001 Feb
Propofol action in both spinal cord and brain blunts electroencephalographic responses to noxious stimulation in goats.
2001 Feb 1
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.
2001 Jan
Nicorandil accelerates recovery of neuromuscular block caused by vecuronium.
2001 Jan
[Anesthesia for a patient with cardiac sarcoidosis].
2001 Jan
[Anesthetic experience of emergency coronary artery bypass graft operation in a patient with cardioamyloidosis].
2001 Jan
A follow-up study on occupational exposure to inhaled anaesthetics in Eastern European surgeons and circulating nurses.
2001 Jan
Brief exposure to -Gz reduces cerebral perfusion pressure during subsequent +Gz stress in rats.
2001 Jan
Effect of hyperoxia, hypercapnia, and hypoxia on cerebral interstitial oxygen tension and cerebral blood flow.
2001 Jan
The effects of anesthetics on cortical spreading depression elicitation and c-fos expression in rats.
2001 Jan
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.
2001 Jan
Effect of isoflurane versus nicardipine on blood flow of lumbar paraspinal muscles during controlled hypotension for spinal surgery.
2001 Jan 1
Respiratory reflexes in response to upper-airway administration of sevoflurane and isoflurane in anesthetized, spontaneously breathing dogs.
2001 Jan-Feb
[The effect of anesthetic technique on recovery from neuromuscular blockade with cisatracurium].
2001 Mar
Effects of isoflurane, enflurane, and halothane on skeletal muscle microcirculation in the endotoxemic rat.
2001 Mar
The effect of epidural anesthesia on respiratory distress induced by airway occlusion in isoflurane-anesthetized cats.
2001 Mar
The effect of the preemptive use of the NMDA receptor antagonist dextromethorphan on postoperative analgesic requirements.
2001 Mar
The effect of chronic cocaine administration on hemodynamic stability and neurohumoral mediators during isoflurane anesthesia and shock in rats.
2001 Mar
Recovery profile and side effects of remifentanil-based anaesthesia with desflurane or propofol for laparoscopic cholecystectomy.
2001 Mar
Reduced isoflurane consumption with bispectral index monitoring.
2001 Mar
Evidence for a common binding cavity for three general anesthetics within the GABAA receptor.
2001 Mar 15
Intrathecal magnesium sulfate attenuates algogenic behavior and spinal amino acids release after kainic acid receptor activation in rats.
2001 Mar 30
Composition of CO(2) absorbents.
2001 May
Modulation of NMDA receptor function by ketamine and magnesium. Part II: interactions with volatile anesthetics.
2001 May
The efficacy and resource utilization of remifentanil and fentanyl in fast-track coronary artery bypass graft surgery: a prospective randomized, double-blinded controlled, multi-center trial.
2001 May
A randomized double-blinded multicenter comparison of remifentanil versus fentanyl when combined with isoflurane/propofol for early extubation in coronary artery bypass graft surgery.
2001 May
Clonidine decreases intraoperative bleeding in middle ear microsurgery.
2001 May
Ease of laryngeal passage during fibreoptic intubation: a comparison of three endotracheal tubes.
2001 May
Does discontinuation of desflurane at the time of neostigmine administration speed recovery from cisatracurium block compared to that with a propofol-based technique?
2001 May
Haemodynamic changes and vasopressin release are not consistently associated with carbon dioxide pneumoperitoneum in humans.
2001 May
Patents

Patents

Sample Use Guides

Inspired concentrations of 1.5 to 3.0% isoflurane usually produce surgical anesthesia in 7 to 10 minutes.
Route of Administration: Respiratory
The effects of isoflurane and enflurane on spontaneous action potential firing were investigated by extracellular voltage recordings from ventral horn interneurones in cultured spinal cord tissue slices obtained from embryonic rats. Spinal cord slices were continuously perfused with an artificial cerebrospinal fluid (ACSF). Test solutions including isoflurane (0.32 mM) was prepared by dissolving the liquid form in ACSF equilibrated with 95% oxygen and 5% carbon dioxide. Anaesthetics were administered via bath perfusion
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:56:49 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:49 UTC 2021
Record UNII
CYS9AKD70P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOFLURANE
EP   GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
FORANE
Brand Name English
ISOFLURANE [INN]
Common Name English
ISOFLURANE [USAN]
Common Name English
ETHANE, 2-CHLORO-2-(DIFLUOROMETHOXY)-1,1,1-TRIFLUORO-
Systematic Name English
ISOFLURANE [WHO-DD]
Common Name English
ISOFLURANE [MART.]
Common Name English
ISOFLURANE [MI]
Common Name English
ISOFLURANE [USP MONOGRAPH]
Common Name English
1-CHLORO-2,2,2-TRIFLUROETHYL DIFLUROMETHYL ETHER
Systematic Name English
ISOFLURANE [EP MONOGRAPH]
Common Name English
ISOFLURANE [JAN]
Common Name English
ISOFLURANE [ORANGE BOOK]
Common Name English
ISOFLURANE [GREEN BOOK]
Common Name English
COMPOUND-469
Code English
COMPOUND 469
Code English
ISOFLURANE [USP-RS]
Common Name English
ISOFLURANE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175681
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 1.1.1
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
WHO-ATC N01AB06
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
LIVERTOX 519
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
WHO-VATC QN01AB06
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
NDF-RT N0000175975
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
Code System Code Type Description
MERCK INDEX
M6491
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY Merck Index
CAS
26675-46-7
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
LACTMED
Isoflurane
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
RXCUI
6026
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00753
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
NCI_THESAURUS
C65978
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
DRUG CENTRAL
1493
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
FDA UNII
CYS9AKD70P
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
INN
3286
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
EPA CompTox
26675-46-7
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
HSDB
8057
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
IUPHAR
2505
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
WIKIPEDIA
ISOFLURANE
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
MESH
D007530
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
PUBCHEM
3763
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
EVMPD
SUB08319MIG
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL1256
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
USP_CATALOG
1349003
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
247-897-7
Created by admin on Fri Jun 25 20:56:49 UTC 2021 , Edited by admin on Fri Jun 25 20:56:49 UTC 2021
PRIMARY
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
Related Record Type Details
ACTIVE MOIETY