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
Physiology in medicine: importance of hypoxic pulmonary vasoconstriction in maintaining arterial oxygenation during acute respiratory failure.	2001	11299064
Anesthesia for Cesarean section and posterior fossa craniotomy in a patient with von Hippel-Lindau disease.	2001 Apr	11339783
Desflurane, compared to halothane, augments phenylephrine-induced contraction in isolated rat aorta smooth muscle.	2001 Apr	11339778
Neostigmine antagonism of rocuronium block during anesthesia with sevoflurane, isoflurane or propofol.	2001 Apr	11339776
Effects of diazepam and flumazenil on minimum alveolar concentrations for dogs anesthetized with isoflurane or a combination of isoflurane and fentanyl.	2001 Apr	11327463
Induction of anaesthesia with desflurane and isoflurane in the rabbit.	2001 Apr	11315168
Inhaled nitric oxide administration during one-lung ventilation in patients undergoing thoracic surgery.	2001 Apr	11312483
The effects of volatile anesthetics on the Q-Tc interval.	2001 Apr	11312477
Desflurane pharmacokinetics during cardiopulmonary bypass.	2001 Apr	11312475
Sevoflurane versus isoflurane in patients undergoing valvular cardiac surgery.	2001 Apr	11312474
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.	2001 Apr	11312471
The effects of sevoflurane and isoflurane on intracranial pressure and cerebral perfusion pressure after diffuse brain injury in rats.	2001 Apr	11294452
Thoracic epidural anesthesia combined with general anesthesia: the preferred anesthetic technique for thoracic surgery.	2001 Apr	11273913
Effects of chronic exposure to anaesthetic gases on some immune parameters.	2001 Apr 10	11327388
Isoflurane enhances glutamate uptake via glutamate transporters in rat glial cells.	2001 Apr 17	11303749
Cardiac remodeling and contractile function in acid alpha-glucosidase knockout mice.	2001 Apr 27	11328962
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
[Epileptogenic drugs in anesthesia].	2001 Feb	11270238
[Malignant hyperthermia in a pig anesthesized with desflurane].	2001 Feb	11257956
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].	2001 Feb	11257953
[Computer simulation and pharmacoeconomics. Computer simulation as an aid for the analysis of operating room efficiency: an example].	2001 Feb	11252577
[Clinical evaluation of roxatidine acetate hydrochlorides as a preanesthetic medication].	2001 Feb	11244765
No effect of albinism on sedative-hypnotic sensitivity to ethanol and anesthetics.	2001 Feb	11236829
Minimal flow sevoflurane and isoflurane anaesthesia and impact on renal function.	2001 Jan	11270009
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.	2001 Jan	11270005
[First experience in the use of isoflurane in minor surgical interventions in children].	2001 Jan-Feb	11338526
[Oxygen transport parameters in halothane and isoflurane anesthesia with the low gas flow in children].	2001 Jan-Feb	11338509
[The effect of anesthetic technique on recovery from neuromuscular blockade with cisatracurium].	2001 Mar	11333795
Derived fuzzy knowledge model for estimating the depth of anesthesia.	2001 Mar	11327499
Pediatric renal transplantation: anesthesia and perioperative complications.	2001 Mar	11315282
Interaction between nitric oxide and renal myogenic autoregulation in normotensive and hypertensive rats.	2001 Mar	11294600
Respiratory reflexes in spontaneously breathing anesthetized dogs in response to nasal administration of sevoflurane, isoflurane, or halothane.	2001 Mar	11277193
Effects of isoflurane, enflurane, and halothane on skeletal muscle microcirculation in the endotoxemic rat.	2001 Mar	11230718
The effect of epidural anesthesia on respiratory distress induced by airway occlusion in isoflurane-anesthetized cats.	2001 Mar	11226113
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
Minimal alveolar concentration of desflurane in combination with an infusion of medetomidine for the anaesthesia of ponies.	2001 Mar 3	11292086
Intrathecal magnesium sulfate attenuates algogenic behavior and spinal amino acids release after kainic acid receptor activation in rats.	2001 Mar 30	11248436
Composition of CO(2) absorbents.	2001 May	11323380
Modulation of NMDA receptor function by ketamine and magnesium. Part II: interactions with volatile anesthetics.	2001 May	11323344
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
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	11323327
Coagulation assessment in healthy pigs undergoing single xenon anaesthesia and combinations with isoflurane and sevoflurane.	2001 May	11309018
Clonidine decreases intraoperative bleeding in middle ear microsurgery.	2001 May	11309017
Ease of laryngeal passage during fibreoptic intubation: a comparison of three endotracheal tubes.	2001 May	11309016
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	11309015
Haemodynamic changes and vasopressin release are not consistently associated with carbon dioxide pneumoperitoneum in humans.	2001 May	11308999
Anesthetic inhibition in ischemic and nonischemic murine heart: comparison with conscious echocardiographic approach.	2001 May	11299243
Single-channel basis for conductance increase induced by isoflurane in Shaker H4 IR K(+) channels.	2001 May	11287326

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