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

3.14323206E11
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
Cancer and congenital anomalies associated with anesthetics.
1976
Ketamine potentiates cerebrocortical damage induced by the common anaesthetic agent nitrous oxide in adult rats.
2000 Aug
Physiology in medicine: importance of hypoxic pulmonary vasoconstriction in maintaining arterial oxygenation during acute respiratory failure.
2001
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
Inhaled nitric oxide administration during one-lung ventilation in patients undergoing thoracic surgery.
2001 Apr
The effects of volatile anesthetics on the Q-Tc interval.
2001 Apr
Isoflurane enhances glutamate uptake via glutamate transporters in rat glial cells.
2001 Apr 17
[Epileptogenic drugs in anesthesia].
2001 Feb
No effect of albinism on sedative-hypnotic sensitivity to ethanol and anesthetics.
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
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
Cerebral hemodynamic response to the introduction of desflurane: a comparison with sevoflurane.
2001 Jan
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes.
2001 Jan
Neither GABA(A) nor strychnine-sensitive glycine receptors are the sole mediators of MAC for isoflurane.
2001 Jan
Respiratory reflexes in response to upper-airway administration of sevoflurane and isoflurane in anesthetized, spontaneously breathing dogs.
2001 Jan-Feb
The effect of epidural anesthesia on respiratory distress induced by airway occlusion in isoflurane-anesthetized cats.
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
Minimal alveolar concentration of desflurane in combination with an infusion of medetomidine for the anaesthesia of ponies.
2001 Mar 3
Coagulation assessment in healthy pigs undergoing single xenon anaesthesia and combinations with isoflurane and sevoflurane.
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 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 Wed Jul 05 23:51:12 UTC 2023
Edited
by admin
on Wed Jul 05 23:51:12 UTC 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 Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 1.1.1
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
NCI_THESAURUS C245
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
WHO-ATC N01AB06
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
LIVERTOX NBK548501
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
WHO-VATC QN01AB06
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
NDF-RT N0000175975
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
Code System Code Type Description
MERCK INDEX
M6491
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY Merck Index
CAS
26675-46-7
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
LACTMED
Isoflurane
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
RXCUI
6026
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY RxNorm
CHEBI
6015
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
DRUG BANK
DB00753
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
NCI_THESAURUS
C65978
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
DRUG CENTRAL
1493
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
FDA UNII
CYS9AKD70P
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
INN
3286
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID3020752
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
HSDB
8057
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
IUPHAR
2505
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
WIKIPEDIA
ISOFLURANE
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
DAILYMED
CYS9AKD70P
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
MESH
D007530
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
PUBCHEM
3763
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
EVMPD
SUB08319MIG
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1256
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1349003
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
SMS_ID
100000091651
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
247-897-7
Created by admin on Wed Jul 05 23:51:12 UTC 2023 , Edited by admin on Wed Jul 05 23:51:12 UTC 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