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

Details

Stereochemistry RACEMIC
Molecular Formula C3H2ClF5O
Molecular Weight 184.492
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOFLURANE

SMILES

FC(F)OC(Cl)C(F)(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 184.492
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

1979
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
n = 1
Health Status: unhealthy
Age Group: 25 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 4 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Anesthesia for Cesarean section and posterior fossa craniotomy in a patient with von Hippel-Lindau disease.
2001 Apr
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
Induction of anaesthesia with desflurane and isoflurane in the rabbit.
2001 Apr
The effects of volatile anesthetics on the Q-Tc interval.
2001 Apr
Desflurane pharmacokinetics during cardiopulmonary bypass.
2001 Apr
Sevoflurane versus isoflurane in patients undergoing valvular cardiac surgery.
2001 Apr
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.
2001 Apr
The effects of sevoflurane and isoflurane on intracranial pressure and cerebral perfusion pressure after diffuse brain injury in rats.
2001 Apr
Thoracic epidural anesthesia combined with general anesthesia: the preferred anesthetic technique for thoracic surgery.
2001 Apr
Cardiac remodeling and contractile function in acid alpha-glucosidase knockout mice.
2001 Apr 27
Increase in rat plasma antioxidant activity after E. coli lipopolysaccharide administration.
2001 Feb
An experimental study on the relationship of intra-abdominal pressure and renal ischemia.
2001 Feb
[Epileptogenic drugs in anesthesia].
2001 Feb
[Malignant hyperthermia in a pig anesthesized with desflurane].
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
Can anesthesiologic strategies for caesarean section influence newborn jaundice? A retrospective and prospective study.
2001 Feb
High concentrations of isoflurane do not block the sympathetic nervous system activation from desflurane.
2001 Feb
Minimal flow sevoflurane and isoflurane anaesthesia and impact on renal function.
2001 Jan
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.
2001 Jan
Preanaesthetic use of atropine in small animals.
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
[The effects of intravenous nicardipine on jugular venous oxygen saturation].
2001 Jan
[First experience in the use of isoflurane in minor surgical interventions in children].
2001 Jan-Feb
[Oxygen transport parameters in halothane and isoflurane anesthesia with the low gas flow in children].
2001 Jan-Feb
Interaction between nitric oxide and renal myogenic autoregulation in normotensive and hypertensive rats.
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 effects of low-flow sevoflurane and isoflurane anesthesia on renal function in patients with stable moderate renal insufficiency.
2001 Mar
Acute canine model for drug-induced Torsades de Pointes in drug safety evaluation-influences of anesthesia and validation with quinidine and astemizole.
2001 Mar
PBPK modeling of canine inhalation exposures to halogenated hydrocarbons.
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
Evidence for a common binding cavity for three general anesthetics within the GABAA receptor.
2001 Mar 15
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels.
2001 Mar 23
Minimal alveolar concentration of desflurane in combination with an infusion of medetomidine for the anaesthesia of ponies.
2001 Mar 3
Intrathecal magnesium sulfate attenuates algogenic behavior and spinal amino acids release after kainic acid receptor activation in rats.
2001 Mar 30
Coagulation assessment in healthy pigs undergoing single xenon anaesthesia and combinations with isoflurane and sevoflurane.
2001 May
Clonidine decreases intraoperative bleeding in middle ear microsurgery.
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
Anesthetic inhibition in ischemic and nonischemic murine heart: comparison with conscious echocardiographic approach.
2001 May
Single-channel basis for conductance increase induced by isoflurane in Shaker H4 IR K(+) channels.
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 using gas-tight syringe pumps. The flow rate was approximately 1 ml min-1. To ensure steady-state conditions, recordings during anaesthetic treatment were carried out 10–15 min after starting the perfusate change.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:24:53 GMT 2023
Edited
by admin
on Fri Dec 15 16:24:53 GMT 2023
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
(2RS)-2-chloro-2-(difluoromethoxy)-1,1,1-trifluoroethane
Systematic 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
DESFLURANE IMPURITY B [EP IMPURITY]
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 Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 1.1.1
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
WHO-ATC N01AB06
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
LIVERTOX NBK548501
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
WHO-VATC QN01AB06
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
NDF-RT N0000175975
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
Code System Code Type Description
MERCK INDEX
m6491
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY Merck Index
CAS
26675-46-7
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
LACTMED
Isoflurane
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
RXCUI
6026
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PRIMARY RxNorm
CHEBI
6015
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PRIMARY
DRUG BANK
DB00753
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PRIMARY
NCI_THESAURUS
C65978
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PRIMARY
DRUG CENTRAL
1493
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PRIMARY
FDA UNII
CYS9AKD70P
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
INN
3286
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PRIMARY
EPA CompTox
DTXSID3020752
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PRIMARY
HSDB
8057
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PRIMARY
IUPHAR
2505
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
WIKIPEDIA
ISOFLURANE
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
DAILYMED
CYS9AKD70P
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
MESH
D007530
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PRIMARY
PUBCHEM
3763
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PRIMARY
EVMPD
SUB08319MIG
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PRIMARY
ChEMBL
CHEMBL1256
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PRIMARY
RS_ITEM_NUM
1349003
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PRIMARY
SMS_ID
100000091651
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PRIMARY
ECHA (EC/EINECS)
247-897-7
Created by admin on Fri Dec 15 16:24:54 GMT 2023 , Edited by admin on Fri Dec 15 16:24:54 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> AGONIST
TARGET -> INHIBITOR
TARGET -> AGONIST
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
Related Record Type Details
ACTIVE MOIETY