SynCED: Enflurane

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:19 UTC

Update Date

2026-05-14 16:24:48 UTC

Accession Number

CHEM002146

Identification

Common Name

Enflurane

Class

Small Molecule

Description

Enflurane is only found in individuals that have used or taken this drug. It is an extremely stable inhalation anesthetic that allows rapid adjustments of anesthesia depth with little change in pulse or respiratory rate. [PubChem]Enflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Enflurane 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. Enflurane also binds to and angonizes the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glycine receptor, and antagonizes the glutamate receptor receptor. These yield a decreased depolarization and therefore, tissue excitability which results in anesthesia.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anesthetic
Anesthetic, Inhalation
Drug
General Anesthetic
Human Neurotoxin
Lachrymator
Metabolite
Organic Compound
Organochloride
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Chloro-1,1,2-trifluoroethyl difluoromethyl ether	ChEBI
Alyrane	ChEBI
Efrane	ChEBI
Ethrane	ChEBI
Methylflurether	ChEBI
Anesthetic 347	HMDB
Anesthetic compound no. 347	HMDB
Compound 347	HMDB
Ohio 347	HMDB
Zeneca brand OF enflurane	HMDB
Pisa brand OF enflurane	HMDB
Enlirane	HMDB
Abbott brand OF enflurane	HMDB
Baxter anaesthesia brand OF enflurane	HMDB
AstraZeneca brand OF enflurane	HMDB
Enfran	HMDB
Etran	HMDB

Chemical Formula

C₃H₂ClF₅O

Average Molecular Mass

184.492 g/mol

Monoisotopic Mass

183.971 g/mol

CAS Registry Number

13838-16-9

IUPAC Name

2-chloro-1-(difluoromethoxy)-1,1,2-trifluoroethane

Traditional Name

enflurane

SMILES

FC(F)OC(F)(F)C(F)Cl

InChI Identifier

InChI=1S/C3H2ClF5O/c4-1(5)3(8,9)10-2(6)7/h1-2H

InChI Key

JPGQOUSTVILISH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organofluorides. Organofluorides are compounds containing a chemical bond between a carbon atom and a fluorine atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organofluorides

Sub Class

Not Available

Direct Parent

Organofluorides

Alternative Parents

Substituents

Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organofluoride
Organochloride
Alkyl halide
Alkyl fluoride
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organofluorine compound (CHEBI:4792 )
organochlorine compound (CHEBI:4792 )
ether (CHEBI:4792 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	56.5
Solubility	5620 mg/L (at 37°C)

Predicted Properties

Property	Value	Source
Water Solubility	3.9 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	23.07 m³·mol⁻¹	ChemAxon
Polarizability	9.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Rapidly absorbed into the circulation via the lungs.

Mechanism of Toxicity

Enflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Enflurane 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. Enflurane also binds to and angonizes the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glycine receptor, and antagonizes the glutamate receptor receptor. These yield a decreased depolarization and therefore, tissue excitability which results in anesthesia.

Metabolism

2.4% of the dose is slowly metabolized hepatically via oxidation and dehalogenation (primarily through the actions of cytochrome P450 2E1). Leads to low levels of serum fluoride (15 µmol/L).

Toxicity Values

LD50: 5.4 ml/kg (oral, rat).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used for the induction and maintenance of general anaesthesia during surgery and cesarean section and also used for analgesia during vaginal delivery.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of acute overdose include nausea, vomiting, irritation to the eyes, skin and nose/throat, headache, dizziness, and drowsiness. Symptoms of chronic overdose include hypotension, cardiac arrhythmias, respiratory depression, and liver/kidney dysfunction.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00228

HMDB ID

HMDB0014373

FooDB ID

Not Available

Phenol Explorer ID