Isoflurane (CED0000672)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:35 UTC

Update Date

2026-05-14 16:47:56 UTC

Accession Number

CHEM002266

Identification

Common Name

Isoflurane

Class

Small Molecule

Description

Isoflurane belongs to the organofluorides, a class of organohalogen compounds within the organic compounds. It is an exogenous liquid at room temperature with the formula C3H2ClF5O and an average molecular weight of 184.49 g/mol. Used as an inhalation anaesthetic, its recorded exposure routes include respiratory and inhalation (PMC10097713, PMC10469338, PMC10609273, PMC10757425, PMC10922143, PMC10925143, PMC11342404, PMC11373598, PMC11579412, PMC11634801). The compound is found in or released from 33 recorded sources, including anesthetics in healthcare, pharmaceuticals and veterinary products; food preservation, the processing of meats, and the preparation of vinegar and wine or sparkling wine; household cleaning and consumer products such as soap detergents, soap dispensers, pipe accessories, cigar cigarettes, and non electric simulated smoking devices; building and construction materials including floors, ceilings, roofs, fencing, and sunshades awnings or outside screens; and electrical and electronic equipment such as amplifiers, antennas, electric switches, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. Isoflurane interacts with 27 recorded protein targets, including Calcium-transporting ATPase type 2C member 1 (ATP2C1), ATP synthase F(1) complex subunit delta, mitochondrial (ATP5F1D), NADH-ubiquinone oxidoreductase chain 1 (MT-ND1), and Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1). It acts as an antagonist, positive allosteric modulator, or other unknown modulator of Gamma-aminobutyric acid receptor subunit pi (GABRP), subunit delta (GABRD), subunit beta-1 (GABRB1), subunit gamma-2 (GABRG2), and 16 other proteins. It binds to the GABA receptor, the glycine receptor, the glutamate receptor, and the large conductance Ca2+ activated potassium channel. Additionally, it appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane and induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times.

Contaminant Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Chloro-2,2,2-trifluoroethyl difluoromethyl ether	ChEBI
Aerrane	ChEBI
Ethane	ChEBI
Forane	ChEBI
Forene	ChEBI
Isoflurano	ChEBI
Isofluranum	ChEBI

Chemical Formula

C₃H₂ClF₅O

Average Molecular Mass

184.492 g/mol

Monoisotopic Mass

183.971 g/mol

CAS Registry Number

26675-46-7

IUPAC Name

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

Traditional Name

isoflurane

SMILES

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

InChI Identifier

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

InChI Key

PIWKPBJCKXDKJR-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:6015 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

inhalation anaesthetic

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	48-48.5°C
Boiling Point	48.5°C
Solubility	4470 mg/L (at 37°C)

Predicted Properties

Property	Value	Source
Water Solubility	3.56 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.84	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	-4.7	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	23.04 m³·mol⁻¹	ChemAxon
Polarizability	9.73 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0udi-9400000000-6ed40f9f8dd595d42648	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-86cdc849d98cebceb41f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-638085524e003bcf4003	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-9400000000-d8b25b66c3eceff9f5ab	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-ebe1660e853c066c6392	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01q9-0900000000-30bbfd349d22f8057b18	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-4900000000-0717c6cbf8950b9de9d8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-f72d585725966be19d66	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-db40d4801d1fbe19bc48	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03e9-1900000000-8de2342c64e7c06ad3bb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-cda3ea1a89b8c052a64a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-cda3ea1a89b8c052a64a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1900000000-90e8f4a64ee24b4cbf9b	Not Available	View Spectrum
MS	MS Spectrum	splash10-0udi-9300000000-c134e176400bbe7073c2	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor. LC50=15300 ppm/3 hrs (inhalation by rat)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

The predicted effects of acute overexposure by inhalation of Isoflurane, USP include headache, dizziness or (in extreme cases) unconsciousness. (1)

Treatment

Stop drug administration, establish a clear airway, and initiate assisted or controlled ventilation with pure oxygen. (2)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2177.0	Log mg/kg	[1200:3900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
233	Brushes	Personal care & cosmetics	Not Available
369	Anesthetics	Healthcare, pharmaceuticals & veterinary products	Not Available
495	Ceilings	Building & Construction	Not Available
496	Fencing	Building & Construction	Not Available
497	Floors	Building & Construction	Not Available
499	Roofs	Building & Construction	Not Available
501	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
502	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
503	Tents Or Canopies	Building & Construction	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
524	Hybrid Capacitors	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
538	Thin Magnetic Films	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
553	Treatment Of Hops	Food, food processing & cookware	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
563	Soap Detergents	Household cleaning & consumer products	Not Available
564	Soap Dispensers	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
583	Anchoring Equipment	Marine, shipping & aquaculture	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
596	Acaricides	Agriculture & land management	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
602	Molluscicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
635	Buttons	Textiles, leather & furnishings	Not Available
640	Embroidering And Tufting	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
647	Multicolour Dyeing	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available
657	Surface Finishing Of Leather	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Isoflurane GABA(A) Anesthetic Action Pathway

Isoflurane Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Fatty-acid amide hydrolase 1	O08914	Mus musculus	Predicted (SEA)	7166.33
Click to view 3D structure	Monoglyceride lipase	Q99685	Humans	Predicted (SEA)	7594.35
Click to view 3D structure	Monoacylglycerol lipase ABHD6	Q9BV23	Humans	Predicted (SEA)	7042.71
Click to view 3D structure	AP2-associated protein kinase 1	Q2M2I8	Humans	Predicted (SEA)	7742.96
Click to view 3D structure	Cholesteryl ester transfer protein	P22687	Oryctolagus cuniculus	Predicted (SEA)	2220.49
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	7781.96
Click to view 3D structure	Platelet-activating factor acetylhydrolase	Q13093	Humans	Predicted (SEA)	5948.3
Click to view 3D structure	Monoglyceride lipase	O35678	Mus musculus	Predicted (SEA)	7374.66
Click to view 3D structure	BMP-2-inducible protein kinase	Q9NSY1	Humans	Predicted (SEA)	7748.8
Click to view 3D structure	MAP kinase-interacting serine/threonine-protein kinase 1	Q9BUB5	Humans	Predicted (SEA)	7736.19
Click to view 3D structure	Voltage-gated potassium channel KCNC1	P25122	Rattus norvegicus	Predicted (SEA)	1844.87
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	7781.65
Click to view 3D structure	ACCase	H9BT73	Alopecurus japonicus	Predicted (SEA)	4810.23
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	7780.41
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	7783.21
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	7782.28
Click to view 3D structure	Citron Rho-interacting kinase	O14578	Humans	Predicted (SEA)	7751.06
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	7783.05
Click to view 3D structure	Cyclin-G-associated kinase	O14976	Humans	Predicted (SEA)	7765.62
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	7780.87
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	7783.52
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	7783.13
Click to view 3D structure	MAP kinase-interacting serine/threonine-protein kinase 2	Q9HBH9	Humans	Predicted (SEA)	7779.01
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2B	Q00960	Rattus norvegicus	Predicted (SEA)	7712.44
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	7783.83
Click to view 3D structure	ATP synthase F(1) complex subunit delta, mitochondrial	P30049	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.
Click to view 3D structure	Calcium-transporting ATPase type 2C member 1	P98194	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-1	P14867	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.
Click to view 3D structure	Glycine receptor subunit alpha-1	P23415	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.
Click to view 3D structure	NADH-ubiquinone oxidoreductase chain 1	P03886	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.
Click to view 3D structure	Potassium voltage-gated channel subfamily A member 1	Q09470	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.
Click to view 3D structure	Glutamate receptor 1	P42261	Humans	Known	Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.