Identification

Name
Desflurane
Accession Number
DB01189
Description

Desflurane is a highly fluorinated methyl ethyl ether used for maintenance of general anaesthesia. Volatile agents such as desflurane may activate GABA channels and hyperpolarize cell membranes. In addition, they may inhibit certain calcium channels and therefore prevent release of neurotransmitters and inhibit glutamate channels. Volatile anesthetics easily partition into cellular membranes and could expand the volume of the cell membrane and subsequently distort channels necessary for sodium ion flux and the development of action potentials necessary for synaptic transmission. Desflurane preconditions human myocardium against ischemia through activation of mitochondrial K(ATP) channels, adenosine A1 receptor, and alpha and beta adrenoceptors.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 168.0378
Monoisotopic: 168.000983916
Chemical Formula
C3H2F6O
Synonyms
  • (±)-2-difluoromethyl 1,2,2,2-tetrafluoroethyl ether
  • 1,1,1,2-tetrafluoro-2-(difluoromethoxy)ethane
  • Desflurane
  • Desflurano
  • Desfluranum
  • Difluoromethyl 1,2,2,2-tetrafluoroethyl ether

Pharmacology

Indication

For use as an inhalation agent for induction and/or maintenance of anesthesia for inpatient and outpatient surgery in adults.

Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Desflurane is a general inhalation anesthetic. It induces muscle relaxation and reduces pains sensitivity by altering tissue excitability. It does so by decreasing the extent of gap junction mediated cell-cell coupling and altering the activity of the channels that underlie the action potential.

Mechanism of action

Desflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Desflurane 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. Desflurane also binds to and agonizes the GABA receptor, the large conductance Ca2+ activated potassium channel, the glycine receptors, and antagonizes the glutamate receptors.

TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGlycine receptor subunit alpha-1
agonist
Humans
AGlutamate receptor 1
antagonist
Humans
APotassium voltage-gated channel subfamily A member 1
inducer
Humans
UATP synthase subunit delta, mitochondrial
other/unknown
Humans
ANADH-ubiquinone oxidoreductase chain 1
inhibitor
Humans
ACalcium transporting ATPases
inhibitor
Humans
Absorption

Rapidly absorbed into the circulation via the lungs following inhalation.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Minimally biotransformed in the liver in humans (approximately 0.02% of the quantity absorbed).

Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Voltage-dependent L-type calcium channel subunit alpha-1S---Not Availablec.3257G>A / c.520C>TADR InferredMalignant hyperthermia.Details
Ryanodine receptor 1---Not Availablec.103T>C / c.487C>T  … show all ADR InferredMalignant hyperthermia.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of QTc prolongation can be increased when Desflurane is combined with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Desflurane is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Desflurane is combined with Acemetacin.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Desflurane.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Desflurane.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Desflurane.
AclidiniumDesflurane may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Desflurane is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Desflurane is combined with Adenosine.
AgomelatineThe risk or severity of adverse effects can be increased when Desflurane is combined with Agomelatine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DesfluraneLiquid100 %Respiratory (inhalation)Blue Zone Technologies LtdNot applicableNot applicableCanada flag
SupraneLiquid240 mL/240mLRespiratory (inhalation)Baxter Healthcare Corporation1992-09-18Not applicableUS flag
SupraneLiquid1.5 g/1mLRespiratory (inhalation)Baxter Healthcare Corporation2006-08-142006-08-14US flag
SupraneLiquid240 mL/240mLRespiratory (inhalation)Baxter Healthcare Corporation1992-09-18Not applicableUS flag
SupraneLiquid100 %Respiratory (inhalation)Baxter Laboratories1996-12-23Not applicableCanada flag
SupraneLiquid240 mL/240mLRespiratory (inhalation)Baxter Healthcare Corporation1992-09-18Not applicableUS flag
SupraneLiquid240 mL/240mLRespiratory (inhalation)General Injectables & Vaccines, Inc2012-04-25Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DesfluraneLiquid240 mL/240mLRespiratory (inhalation)Sandoz Inc.2018-02-26Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
N01AB07 — Desflurane
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as organofluorides. These 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
Organooxygen compounds / Hydrocarbon derivatives / Alkyl fluorides
Substituents
Aliphatic acyclic compound / Alkyl fluoride / Alkyl halide / Hydrocarbon derivative / Organic oxygen compound / Organofluoride / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organofluorine compound (CHEBI:4445)

Chemical Identifiers

UNII
CRS35BZ94Q
CAS number
57041-67-5
InChI Key
DPYMFVXJLLWWEU-UHFFFAOYSA-N
InChI
InChI=1S/C3H2F6O/c4-1(3(7,8)9)10-2(5)6/h1-2H
IUPAC Name
2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane
SMILES
FC(F)OC(F)C(F)(F)F

References

Synthesis Reference

Leonid A. Rozov, Chialang Huang, Gerald G. Vernice, "Synthesis of desflurane." U.S. Patent US5205914, issued June, 1991.

US5205914
General References
Not Available
Human Metabolome Database
HMDB0015320
KEGG Drug
D00546
KEGG Compound
C07519
PubChem Compound
42113
PubChem Substance
46505270
ChemSpider
38403
RxNav
27340
ChEBI
4445
ChEMBL
CHEMBL1200733
Therapeutic Targets Database
DAP000693
PharmGKB
PA164749136
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Desflurane
AHFS Codes
  • 28:04.16 — Inhalation Anesthetics
FDA label
Download (174 KB)
MSDS
Download (51.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceAnaesthesia therapy / BMI >30 kg/m21
4CompletedBasic ScienceAnesthesia; Bariatric Surgery1
4CompletedDiagnosticAnaesthesia1
4CompletedDiagnosticOxygen Saturation1
4CompletedDiagnosticPostoperative Delirium1
4CompletedHealth Services ResearchEmergence Agitation1
4CompletedOtherAnaesthesia therapy1
4CompletedOtherLung Volume Reduction Surgery1
4CompletedPreventionAdjunct to general anesthesia therapy / Strabismus1
4CompletedPreventionEnd Stage Liver Diseases1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
  • General Injectables and Vaccines Inc.
Dosage Forms
FormRouteStrength
SolutionRespiratory (inhalation)100 %
InhalantRespiratory (inhalation)240 mL/240mL
LiquidRespiratory (inhalation)1.5 g/1mL
LiquidRespiratory (inhalation)100 %
LiquidRespiratory (inhalation)240 mL/240mL
SolutionRespiratory (inhalation)100 mL/100mL
Prices
Unit descriptionCostUnit
Suprane inhalation liquid0.76USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5617906No1997-04-082014-10-08US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)23.5 °CNot Available
water solubilityNegligibleNot Available
logP1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.54 mg/mLALOGPS
logP2.19ALOGPS
logP2.4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)18.87ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity18.12 m3·mol-1ChemAxon
Polarizability7.89 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9941
Caco-2 permeable+0.626
P-glycoprotein substrateNon-substrate0.883
P-glycoprotein inhibitor INon-inhibitor0.9415
P-glycoprotein inhibitor IINon-inhibitor0.9027
Renal organic cation transporterNon-inhibitor0.9311
CYP450 2C9 substrateNon-substrate0.8676
CYP450 2D6 substrateNon-substrate0.919
CYP450 3A4 substrateNon-substrate0.7556
CYP450 1A2 substrateNon-inhibitor0.6194
CYP450 2C9 inhibitorNon-inhibitor0.836
CYP450 2D6 inhibitorNon-inhibitor0.9466
CYP450 2C19 inhibitorNon-inhibitor0.707
CYP450 3A4 inhibitorNon-inhibitor0.9604
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8921
Ames testNon AMES toxic0.9042
CarcinogenicityCarcinogens 0.7045
BiodegradationNot ready biodegradable0.9566
Rat acute toxicity1.2690 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9724
hERG inhibition (predictor II)Non-inhibitor0.909
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name
GLRA1
Uniprot ID
P23415
Uniprot Name
Glycine receptor subunit alpha-1
Molecular Weight
52623.35 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Grasshoff C, Antkowiak B: Effects of isoflurane and enflurane on GABAA and glycine receptors contribute equally to depressant actions on spinal ventral horn neurones in rats. Br J Anaesth. 2006 Nov;97(5):687-94. doi: 10.1093/bja/ael239. Epub 2006 Sep 13. [PubMed:16973644]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Pdz domain binding
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIA1
Uniprot ID
P42261
Uniprot Name
Glutamate receptor 1
Molecular Weight
101505.245 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Dildy-Mayfield JE, Eger EI 2nd, Harris RA: Anesthetics produce subunit-selective actions on glutamate receptors. J Pharmacol Exp Ther. 1996 Mar;276(3):1058-65. [PubMed:8786535]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Voltage-gated potassium channel activity
Specific Function
Voltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain and the central nervous system, but also in the kidney (PubMed:1990381...
Gene Name
KCNA1
Uniprot ID
Q09470
Uniprot Name
Potassium voltage-gated channel subfamily A member 1
Molecular Weight
56465.01 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Matchett GA, Allard MW, Martin RD, Zhang JH: Neuroprotective effect of volatile anesthetic agents: molecular mechanisms. Neurol Res. 2009 Mar;31(2):128-34. doi: 10.1179/174313209X393546. [PubMed:19298752]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5D
Uniprot ID
P30049
Uniprot Name
ATP synthase subunit delta, mitochondrial
Molecular Weight
17489.755 Da
References
  1. Kosk-Kosicka D, Roszczynska G: Inhibition of plasma membrane Ca(2+)-ATPase activity by volatile anesthetics. Anesthesiology. 1993 Oct;79(4):774-80. [PubMed:8214757]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
This action is based on the activity of other volatile anesthetics on this target. It is a potential target for desflurane.
General Function
Nadh dehydrogenase (ubiquinone) activity
Specific Function
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the tra...
Gene Name
MT-ND1
Uniprot ID
P03886
Uniprot Name
NADH-ubiquinone oxidoreductase chain 1
Molecular Weight
35660.055 Da
References
  1. Hanley PJ, Ray J, Brandt U, Daut J: Halothane, isoflurane and sevoflurane inhibit NADH:ubiquinone oxidoreductase (complex I) of cardiac mitochondria. J Physiol. 2002 Nov 1;544(Pt 3):687-93. [PubMed:12411515]
  2. Kayser EB, Suthammarak W, Morgan PG, Sedensky MM: Isoflurane selectively inhibits distal mitochondrial complex I in Caenorhabditis elegans. Anesth Analg. 2011 Jun;112(6):1321-9. doi: 10.1213/ANE.0b013e3182121d37. Epub 2011 Apr 5. [PubMed:21467554]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Signal transducer activity
Specific Function
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of the calcium.

Components:
References
  1. Kosk-Kosicka D: Plasma membrane Ca(2+)-ATPase as a target for volatile anesthetics. Adv Pharmacol. 1994;31:313-22. [PubMed:7873420]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Sawas AH, Pentyala SN, Rebecchi MJ: Binding of volatile anesthetics to serum albumin: measurements of enthalpy and solvent contributions. Biochemistry. 2004 Oct 5;43(39):12675-85. [PubMed:15449957]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2020 01:55

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