SEVOFLURANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H3F7O
Molecular Weight	200.0548
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FCOC(C(F)(F)F)C(F)(F)F

InChI

InChIKey=DFEYYRMXOJXZRJ-UHFFFAOYSA-N

InChI=1S/C4H3F7O/c5-1-12-2(3(6,7)8)4(9,10)11/h2H,1H2

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020478s025s026lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/ultane-drug.htm https://www.drugs.com/cdi/sevoflurane.html http://www.wikidoc.org/index.php/Sevoflurane

Sevoflurane is a general anesthetic that is FDA approved for the induction and maintenance of general anesthesia in adult and pediatric patients for inpatient and outpatient surgery. Sevoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Sevoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. It also appears to bind the D subunit of ATP synthase and NADH dehydogenase and also binds to the GABA receptor. Common adverse reactions include cardiovascular: bradyarrhythmia, hypotension, gastrointestinal: nausea, vomiting, neurologic: somnolence, psychiatric: agitation, respiratory: cough, interrupted breathing and other: shivering.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GABA receptor alpha-1 subunit 19 Target ID: CHEMBL1962 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12960553 \| https://www.ncbi.nlm.nih.gov/pubmed/11412290 \| https://www.ncbi.nlm.nih.gov/pubmed/25139222 \| http://www.drugbank.ca/drugs/DB01236	Agonist 2752
GABA receptor alpha-2 subunit 7 Target ID: CHEMBL4956 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12960553 \| https://www.ncbi.nlm.nih.gov/pubmed/25139222	Agonist 2752
GABA-B receptor 32 Target ID: CHEMBL2111463 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9059206	Modulator 846
Glutamate receptor 1 3 Target ID: P42261 Gene ID: 2890.0 Gene Symbol: GRIA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22672766 \| http://www.drugbank.ca/drugs/DB01236	Antagonist 2849
Acetylcholine receptor; alpha1/beta1/delta/gamma 3 Target ID: CHEMBL1907588 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9009947	Inhibitor 8504	1.5 mM [IC50]
Serotonin 3a (5-HT3a) receptor 48 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11873047 \| https://www.ncbi.nlm.nih.gov/pubmed/20885002	Inhibitor 8504
Glycine receptor (alpha-1/beta) 15 Target ID: CHEMBL2363052 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23565218 \| http://www.drugbank.ca/drugs/DB01236	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020478s025s026lbl.pdf	Preventing		Approved 8583	ULTANE Approved Use Sevoflurane, USP is indicated for induction and maintenance of general anesthesia in adult and pediatric patients for inpatient and outpatient surgery. Sevoflurane, USP should be administered only by persons trained in the administration of general anesthesia. Facilities for maintenance of a patent airway, artificial ventilation, oxygen enrichment, and circulatory resuscitation must be immediately available. Since level of anesthesia may be altered rapidly, only vaporizers producing predictable concentrations of sevoflurane, USP should be used. Launch Date 1995

C_max

Value	Dose	Co-administered	Analyte	Population
26.1 μM DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020478s030lbl.pdf	2.1 % single, respiratory dose: 2.1 % route of administration: Respiratory experiment type: SINGLE co-administered:		FLUORIDE ION plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
25.6 μM DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020478s030lbl.pdf	1.7 % single, respiratory dose: 1.7 % route of administration: Respiratory experiment type: SINGLE co-administered:		FLUORIDE ION plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
33 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020478s030lbl.pdf	2.1 % single, respiratory dose: 2.1 % route of administration: Respiratory experiment type: SINGLE co-administered:		FLUORIDE ION plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
24 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020478s030lbl.pdf	1.7 % single, respiratory dose: 1.7 % route of administration: Respiratory experiment type: SINGLE co-administered:		FLUORIDE ION plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.7 32	CYP2A6 626 CYP2B6 776 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.7 32	inhibitor 4027 Sources: https://link.springer.com/article/10.1007%2Fs00540-011-1167-7	yes [Inhibition 1000 uM]

Drug as victim

Target	Modality	Activity
CYP2A6 626	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/books/NBK534781/	minimal
CYP2B6 776	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/books/NBK534781/	minimal
CYP2E1 729	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/books/NBK534781/	minimal
CYP3A4 1946	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/books/NBK534781/	minimal

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/16368812/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9130	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9130
ChemicalBook	CB1440979	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1440979
eMolecules	891010	https://www.emolecules.com/cgi-bin/more?vid=891010
MolPort	MolPort-001-775-746	https://www.molport.com/shop/molecule-link/MolPort-001-775-746
ZINC	ZINC000001530810	http://zinc15.docking.org/substances/ZINC000001530810

PubMed

Title	Date	PubMed
Different inhibitory effects of volatile anesthetics on T- and L-type voltage-dependent Ca2+ channels in porcine tracheal and bronchial smooth muscles.	2001 Apr	11379691
Minimum alveolar concentration (MAC) of xenon with sevoflurane in humans.	2001 Apr	11379681
Cost optimization in anaesthesia.	2001 Apr	11376525
Influence of aortic blood flow velocity on changes of middle cerebral artery blood flow velocity during isoflurane and sevoflurane anaesthesia.	2001 Apr	11350461
Volatile anaesthetics restore bradykinin and serotonin-induced coronary vasodilation after blocking nitric oxide synthase: lack of anaesthetic effects on KATP channels and prostaglandin pathways.	2001 Apr	11350459
[Changes in sedative level during induction of anesthesia using a single volatile anesthetic].	2001 Apr	11345750
[Recovery characteristics of propofol anesthesia in pediatric outpatients; comparison with sevoflurane anesthesia].	2001 Apr	11345748
Neostigmine antagonism of rocuronium block during anesthesia with sevoflurane, isoflurane or propofol.	2001 Apr	11339776
Total intravenous versus inhalational anaesthesia for colonoscopy: a prospective study of clinical recovery and psychomotor function.	2001 Apr	11314831
The effects of volatile anesthetics on the Q-Tc interval.	2001 Apr	11312477
Sevoflurane versus isoflurane in patients undergoing valvular cardiac surgery.	2001 Apr	11312474
Vital capacity inhalation induction with sevoflurane: an alternative to standard intravenous induction for patients undergoing cardiac surgery.	2001 Apr	11312473
Postoperative epidural analgesia in children after major orthopaedic surgery. A randomised study of the effect on PONV of two anaesthetic techniques: low and high dose i.v. fentanyl and epidural infusions with and without fentanyl.	2001 Apr	11300388
The effects of sevoflurane and isoflurane on intracranial pressure and cerebral perfusion pressure after diffuse brain injury in rats.	2001 Apr	11294452
The use of sevoflurane in acute intermittent porphyria.	2001 Apr	11284854
Comparison of sevoflurane-nitrous oxide anaesthesia with the conventional intravenous-inhalational technique using bispectral index monitoring.	2001 Apr	11284814
Ketorolac is not nephrotoxic in connection with sevoflurane anesthesia in patients undergoing breast surgery.	2001 Apr	11273951
Increased T-wave amplitude after accidental intravascular injection of lidocaine plus bupivacaine without epinephrine in sevoflurane-anesthetized child.	2001 Apr	11273925
The effects of sevoflurane and halothane anesthesia on cerebral blood flow velocity in children.	2001 Apr	11273920
The effect of bispectral index monitoring on anesthetic use and recovery in children anesthetized with sevoflurane in nitrous oxide.	2001 Apr	11273918
Volatile anaesthetic effects on Na+-Ca2+ exchange in rat cardiac myocytes.	2001 Apr 1	11283227
[Epileptogenic drugs in anesthesia].	2001 Feb	11270238
Intravenous ketamine attenuates arterial pressure changes during the induction of anaesthesia with propofol.	2001 Feb	11270030
Anaesthesia in a child with autosomal recessive omodysplasia.	2001 Feb	11261917
Minimal flow sevoflurane and isoflurane anaesthesia and impact on renal function.	2001 Jan	11270009
Regulation of perfusion pressure during cardiopulmonary bypass using sevoflurane.	2001 Jan	11266039
Continuous thoracic epidural anesthesia with 0.2% ropivacaine versus general anesthesia for perioperative management of modified radical mastectomy.	2001 Jun	11375845
Hepatic failure in a child after acetaminophen and sevoflurane exposure.	2001 Jun	11375824
Blockade of AMPA receptors and volatile anesthetics: reduced anesthetic requirements in GluR2 null mutant mice for loss of the righting reflex and antinociception but not minimum alveolar concentration.	2001 Mar	11374610
[The effect of anesthetic technique on recovery from neuromuscular blockade with cisatracurium].	2001 Mar	11333795
[Is the use of sevoflurane in closed circuit in pediatric anesthesia really an economy?].	2001 Mar	11332070
[Low alkali-hydroxide content in soda limes does not lead to reduction of compound A formation from sevoflurane during low-flow anesthesia].	2001 Mar	11315487
Pediatric renal transplantation: anesthesia and perioperative complications.	2001 Mar	11315282
[Anesthetic management of a patient with gunshot injury in the neck and the chest].	2001 Mar	11296441
[Dose-response study of preincisional buprenorphine on emergence time and postoperative analgesic requirement in patients anesthetized with sevoflurane].	2001 Mar	11296435
Respiratory reflexes in spontaneously breathing anesthetized dogs in response to nasal administration of sevoflurane, isoflurane, or halothane.	2001 Mar	11277193
A case of awareness with sevoflurane and epidural anesthesia in ovarian tumorectomy.	2001 May	11377163
Postoperative recovery following outpatient pediatric myringotomy: a comparison between sevoflurane and halothane.	2001 May	11377152
Postoperative nausea and vomiting in paediatric ambulatory surgery: sevoflurane versus spinal anaesthesia with propofol sedation.	2001 May	11359594
Sevoflurane inhalation conscious sedation for children having dental treatment.	2001 May	11350337
The epileptogenic property of sevoflurane and in patients without epilepsy.	2001 May	11323384
Composition of CO(2) absorbents.	2001 May	11323380
Preoperative small-dose ketamine prevented tourniquet-induced arterial pressure increase in orthopedic patients under general anesthesia.	2001 May	11323363
Modulation of NMDA receptor function by ketamine and magnesium. Part II: interactions with volatile anesthetics.	2001 May	11323344
The effect of intranasal fentanyl on the emergence characteristics after sevoflurane anesthesia in children undergoing surgery for bilateral myringotomy tube placement.	2001 May	11323340
The safety and efficacy of sevoflurane anesthesia in infants and children with congenital heart disease.	2001 May	11323338
Sevoflurane protects stunned myocardium through activation of mitochondrial ATP-sensitive potassium channels.	2001 May	11323336
Similar haemodynamic, respiratory and metabolic changes with the use of sevoflurane or halothane in children breathing spontaneously via a laryngeal mask airway.	2001 May	11309019
Coagulation assessment in healthy pigs undergoing single xenon anaesthesia and combinations with isoflurane and sevoflurane.	2001 May	11309018
Comparison of genotoxicity of sevoflurane and isoflurane in human lymphocytes studied in vivo using the comet assay.	2001 May 31	11377249

Patents

Sample Use Guides

In Vivo Use Guide

Surgical levels of anesthesia can usually be achieved with concentrations of 0.5 - 3% sevoflurane with or without the concomitant use of nitrous oxide.

Route of Administration: Respiratory

In Vitro Use Guide

Currents elicited by GABA 0.01 mM were increased by low sevoflurane concentrations to 183% and decreased by high sevoflurane concentrations (> 1 mM) to 34% (P < 0.05). Ten- to 90%-rise times of the currents were reduced by sevoflurane concentration dependently. At GABA (1 mM), peak currents and 10-90%-rise times decreased with increasing sevoflurane concentrations.

Name

Type

Language

SEVOCALM

Preferred Name

English

SEVOFLURANE

Official Name

English

SEVOFLURANE [VANDF]

Common Name

English

SEVOFLO

Brand Name

English

SEVOFLURANE [EMA EPAR VETERINARY]

Common Name

English

SEVOFLURANE [USAN]

Common Name

English

SEVOFLURANE [USP MONOGRAPH]

Common Name

English

SEVOFLURANE [EP MONOGRAPH]

Common Name

English

SEVOFLURANE [USP-RS]

Common Name

English

SEVORANE

Brand Name

English

Sevoflurane [WHO-DD]

Common Name

English

SEVOFLURANE [MART.]

Common Name

English

SEVOFLURANE [MI]

Common Name

English

MR6S4

Code

English

ULTANE

Brand Name

English

SEVOFLURANE [USP IMPURITY]

Common Name

English

NSC-760367

Code

English

SEVOFLURANE [ORANGE BOOK]

Common Name

English

MR-6S4

Code

English

SEVOFLURANE [GREEN BOOK]

Common Name

English

PROPANE, 1,1,1,3,3,3-HEXAFLUORO-2-(FLUOROMETHOXY)-

Systematic Name

English

SEVOFLURANE [JAN]

Common Name

English

sevoflurane [INN]

Common Name

English

SEVOFLURANE [EP IMPURITY]

Common Name

English

Fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

N01AB08