Enflurane

Enflurane

Systematic (IUPAC) name
(RS)-2-chloro-1-(difluoromethoxy)-1,1,2-trifluoro-ethane
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Protein binding	97%
Identifiers
CAS number	13838-16-9
ATC code	N01AB04
PubChem	CID 3226
DrugBank	APRD00234
ChemSpider	3113 Y
UNII	91I69L5AY5 Y
KEGG	D00543 Y
ChEBI	CHEBI:4792
ChEMBL	CHEMBL1257 Y
Chemical data
Formula	C3H2ClF5O
Mol. mass	184.492 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C3H2ClF5O/c4-1(5)3(8,9)10-2(6)7/h1-2H Y Key:JPGQOUSTVILISH-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

Enflurane (2-chloro-1,1,2,-trifluoroethyl-difluoromethyl ether) is a halogenated ether that was commonly used for inhalational anesthesia during the 1970s and 1980s. Developed by Ross Terrell in 1963, it was first used clinically in 1966.

Enflurane is a structural isomer of isoflurane. It vaporizes readily, but is a liquid at room temperature.

Physical properties

Property	Value
Boiling point at 1 atm	56.5 °C
MAC	1.68
Vapor pressure at 20 °C	22.9 kPa (172 mm Hg)
Blood: Gas Partition Coefficient	1.9
Oil: Gas Partition Coefficient	98

Side effects

Clinically, enflurane produces a dose-related depression of myocardial contractility with an associated decrease in myocardial oxygen consumption. Between 2% and 5% of the inhaled dose is oxidised in the liver, producing fluoride ions and difluoromethoxy-difluoroacetic acid. This is significantly higher than the metabolism of its structural isomer isoflurane.

Enflurane also lowers the threshold for seizures, and should especially not be used on people with epilepsy. It is also known to cause malignant hyperthermia.

It relaxes the uterus in pregnant women.

Enflurane and methoxyflurane have a nephrotoxic effect and cause acute renal failure, usually by its nephrotoxic metabolite.