ISOFLURANE

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 Search

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	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017624s036lbl.pdf

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16973644	Positive Allosteric Modulator 179
Glycine receptor 13 Target ID: CHEMBL3392921 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16973644	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017624s036lbl.pdf	Primary		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
800 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23015620/	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

Value	Dose	Co-administered	Analyte	Population
4.765 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23015620/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
18.01 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23015620/	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

Dose	Population	Adverse events
1382.4 % * h multiple, respiratory Highest studied dose Dose: 1382.4 % * h Route: respiratory Route: multiple Dose: 1382.4 % * h Sources: https://pubmed.ncbi.nlm.nih.gov/20841413	unhealthy, 25 years n = 1 Health Status: unhealthy Age Group: 25 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20841413	Sources: https://pubmed.ncbi.nlm.nih.gov/20841413
1975.2 % * h multiple, respiratory Highest studied dose Dose: 1975.2 % * h Route: respiratory Route: multiple Dose: 1975.2 % * h Sources: https://pubmed.ncbi.nlm.nih.gov/20841413	unhealthy, 4 years n = 1 Health Status: unhealthy Age Group: 4 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20841413	Sources: https://pubmed.ncbi.nlm.nih.gov/20841413

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781		inducer 97

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2E1 667	CYP2B6 547 CYP2A6 79 CYP2E1 128

Drug as perpetrator

Target	Modality	Activity
CYP2A6 739	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7720526/	no
CYP2D6 1891	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7720526/	no
CYP2E1 970	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7720526/	no
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7720526/	no
CYP2B6 1001	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7720526/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10078678/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6015	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6015
ChemicalBook	CB8437691	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8437691
MolPort	MolPort-000-153-606	https://www.molport.com/shop/molecule-link/MolPort-000-153-606
eMolecules	891348	https://www.emolecules.com/cgi-bin/more?vid=891348

PubMed

Title	Date	PubMed
Effects of chronic exposure to anaesthetic gases on some immune parameters.	2001 Apr 10	11327388
Increase in rat plasma antioxidant activity after E. coli lipopolysaccharide administration.	2001 Feb	11293489
An experimental study on the relationship of intra-abdominal pressure and renal ischemia.	2001 Feb	11281048
High concentrations of isoflurane do not block the sympathetic nervous system activation from desflurane.	2001 Feb	11220421
Absence of direct antioxidant effects from volatile anesthetics in primary mixed neuronal-glial cultures.	2001 Feb	11176096
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	11176085
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	11167476
Smoking status and body size increase carbon monoxide concentrations in the breathing circuit during low-flow anesthesia.	2001 Feb	11159265
Propofol action in both spinal cord and brain blunts electroencephalographic responses to noxious stimulation in goats.	2001 Feb 1	11204050
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.	2001 Jan	11270005
[Anesthesia for a patient with cardiac sarcoidosis].	2001 Jan	11211755
A follow-up study on occupational exposure to inhaled anaesthetics in Eastern European surgeons and circulating nurses.	2001 Jan	11196076
Effects of isoflurane on nitric oxide metabolism and oxidant status of guinea pig myocardium.	2001 Jan	11152023
Effect of hyperoxia, hypercapnia, and hypoxia on cerebral interstitial oxygen tension and cerebral blood flow.	2001 Jan	11146487
The effects of anesthetics on cortical spreading depression elicitation and c-fos expression in rats.	2001 Jan	11145474
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.	2001 Jan	11145473
Intracranial electroencephalographic changes in deep anesthesia.	2001 Jan	11137657
Cerebral hemodynamic response to the introduction of desflurane: a comparison with sevoflurane.	2001 Jan	11133651
Neither GABA(A) nor strychnine-sensitive glycine receptors are the sole mediators of MAC for isoflurane.	2001 Jan	11133613
Fast-track office-based anesthesia: a comparison of propofol versus desflurane with antiemetic prophylaxis in spontaneously breathing patients.	2001 Jan	11133608
Effect of isoflurane versus nicardipine on blood flow of lumbar paraspinal muscles during controlled hypotension for spinal surgery.	2001 Jan 1	11148653
The effect of epidural anesthesia on respiratory distress induced by airway occlusion in isoflurane-anesthetized cats.	2001 Mar	11226113
The effect of the preemptive use of the NMDA receptor antagonist dextromethorphan on postoperative analgesic requirements.	2001 Mar	11226111
The effects of low-flow sevoflurane and isoflurane anesthesia on renal function in patients with stable moderate renal insufficiency.	2001 Mar	11226095
Evidence for a common binding cavity for three general anesthetics within the GABAA receptor.	2001 Mar 15	11245705
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels.	2001 Mar 23	11263999
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	11323328
Clonidine decreases intraoperative bleeding in middle ear microsurgery.	2001 May	11309017

Patents

Sample Use Guides

In Vivo Use Guide

Inspired concentrations of 1.5 to 3.0% isoflurane usually produce surgical anesthesia in 7 to 10 minutes.

Route of Administration: Respiratory

In Vitro Use Guide

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

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Name

Type

Language

ISOFLURANE

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