Sevoflurane (CHEM002383)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (31)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:42 UTC
Update Date2026-05-14 16:58:58 UTC
Accession NumberCHEM002383
Identification
Common NameSevoflurane
ClassSmall Molecule
DescriptionSevoflurane is only found in individuals that have used or taken this drug. Sevoflurane (2,2,2-trifluoro-1-[trifluoromethyl]ethyl fluoromethyl ether), also called fluoromethyl, is a sweet-smelling, non-flammable, highly fluorinated methyl isopropyl ether used for induction and maintenance of general anesthesia. Together with desflurane, it is replacing isoflurane and halothane in modern anesthesiology. [Wikipedia] 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, the large conductance Ca2+ activated potassium channel, the glutamate receptor, and the glycine receptor.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anesthetic, Inhalation
  • Drug
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Platelet Aggregation Inhibitor
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1,1,3,3,3-Hexafluoro-2-(fluoromethoxy)propaneChEBI
SevofluranChEBI
SevofluranoChEBI
SevofluranumChEBI
UltaneKegg
Fluoromethyl-2,2,2-trifluoro-1-(trifluoromethyl)ethyl etherHMDB
SevoraneHMDB
Fluoromethyl hexafluoroisopropyl etherHMDB
Chemical FormulaC4H3F7O
Average Molecular Mass200.055 g/mol
Monoisotopic Mass200.007 g/mol
CAS Registry Number28523-86-6
IUPAC Name1,1,1,3,3,3-hexafluoro-2-(fluoromethoxy)propane
Traditional Namesevoflurane
SMILESFCOC(C(F)(F)F)C(F)(F)F
InChI IdentifierInChI=1S/C4H3F7O/c5-1-12-2(3(6,7)8)4(9,10)11/h2H,1H2
InChI KeyDFEYYRMXOJXZRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDialkyl ethers
Alternative Parents
Substituents
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling Point58.5°C
SolubilityVery slightly soluble
Predicted Properties
PropertyValueSource
Water Solubility1.48 g/LALOGPS
logP2.44ALOGPS
logP2.27ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)15.07ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity23.3 m³·mol⁻¹ChemAxon
Polarizability9.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-6900000000-783322b6f193100b0153Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-1ccd3b88b47c4b33b79aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0190000000-c0673fdbd2394f328534Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0900000000-ab1dc0054503a1957d1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-3b178265498ce71792eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-a3aa8e896a7c3b9972f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-11ad4425fe274622c1c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-cb98e2a5a8a449a66f97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-cb98e2a5a8a449a66f97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0920000000-386a4844069d263921bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c1b985d8da627d6f0c10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-c1b985d8da627d6f0c10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-c1b985d8da627d6f0c10Spectrum
Toxicity Profile
Route of ExposureRapidly absorbed into circulation via the lungs, however solubility in the blood is low.
Mechanism of ToxicitySevoflurane 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, the large conductance Ca2+ activated potassium channel, the glutamate receptor, and the glycine receptor.
MetabolismRelatively little biotransformation, only 5% is metabolized by cytochrome P450 CYP2E1 to hexafluoroisopropanol (HFIP) with release of inorganic fluoride and CO2. No other metabolic pathways have been identified for sevoflurane. Route of Elimination: The low solubility of sevoflurane facilitates rapid elimination via the lungs. In vivo metabolism studies suggest that approximately 5% of the sevoflurane dose may be metabolized. Up to 3.5% of the sevoflurane dose appears in the urine as inorganic fluoride. Half Life: 15-23 hours
Toxicity ValuesLD50: 10.8 g/kg (Rat) (1) LC50: 49881 ppm/hr (Inhalation, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed for induction and maintenance of general anesthesia in adult and pediatric patients for inpatient and outpatient surgery.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentIn the event of overdosage, or what may appear to be overdosage, the following action should be taken: discontinue administration of sevoflurane, maintain a patent airway, initiate assisted or controlled ventilation with oxygen, and maintain adequate cardiovascular function. (3)
Concentrations
Not Available
DrugBank IDDB01236
HMDB IDHMDB0015366
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSevoflurane
Chemspider ID5017
ChEBI ID9130
PubChem Compound ID5206
Kegg Compound IDC07520
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Ross C. Terrell, “Method for the preparation of sevoflurane.” U.S. Patent US5969193, issued December, 1979.

MSDSLink
General ReferencesNot Available