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Identification
NameDesflurane
Accession NumberDB01189  (APRD00907)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
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
Suprane
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Supraneliquid240 mL/240mLrespiratory (inhalation)Baxter Healthcare Corporation1992-09-18Not applicableUs
Supraneliquid100 %inhalationBaxter Corporation1996-12-23Not applicableCanada
Supraneliquid240 mL/240mLrespiratory (inhalation)General Injectables & Vaccines, Inc2012-04-25Not applicableUs
Supraneliquid240 mL/240mLrespiratory (inhalation)Baxter Healthcare Corporation1992-09-18Not applicableUs
Supraneliquid240 mL/240mLrespiratory (inhalation)Baxter Healthcare Corporation1992-09-18Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIICRS35BZ94Q
CAS number57041-67-5
WeightAverage: 168.0378
Monoisotopic: 168.000983916
Chemical FormulaC3H2F6O
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as halomethanes. These are organic compounds in which at least one of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentHalomethanes
Alternative Parents
Substituents
  • Halomethane
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use as an inhalation agent for induction and/or maintenance of anesthesia for inpatient and outpatient surgery in adults.
PharmacodynamicsDesflurane 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 actionDesflurane 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.
Related Articles
AbsorptionRapidly absorbed into the circulation via the lungs following inhalation.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquidinhalation100 %
Liquidrespiratory (inhalation)240 mL/240mL
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)
US5617906 No1994-10-082014-10-08Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
boiling point23.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

US5205914
General ReferencesNot Available
External Links
ATC CodesN01AB07
AHFS Codes
  • 28:04.00
PDB EntriesNot Available
FDA labelDownload (174 KB)
MSDSDownload (51.1 KB)
Interactions
Drug Interactions
Drug
Atracurium besylateDesflurane may increase the neuromuscular blocking activities of Atracurium besylate.
AzelastineDesflurane may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Desflurane.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
BuprenorphineDesflurane may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
CitalopramDesflurane may increase the QTc-prolonging activities of Citalopram.
DofetilideDesflurane may increase the QTc-prolonging activities of Dofetilide.
DopamineDesflurane may increase the arrhythmogenic activities of Dopamine.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
EphedraEphedra may increase the arrhythmogenic activities of Desflurane.
EphedrineEphedrine may increase the arrhythmogenic activities of Desflurane.
EpinephrineDesflurane may increase the arrhythmogenic activities of Epinephrine.
EthanolDesflurane may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FormoterolDesflurane may increase the arrhythmogenic activities of Formoterol.
GoserelinDesflurane may increase the QTc-prolonging activities of Goserelin.
HydrocodoneDesflurane may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
IsoprenalineDesflurane may increase the arrhythmogenic activities of Isoprenaline.
LeuprolideDesflurane may increase the QTc-prolonging activities of Leuprolide.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Desflurane.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
MethotrimeprazineDesflurane may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MethylphenidateMethylphenidate may increase the hypertensive activities of Desflurane.
MetyrosineDesflurane may increase the sedative activities of Metyrosine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Desflurane.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
MirtazapineDesflurane may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
NorepinephrineDesflurane may increase the arrhythmogenic activities of Norepinephrine.
OrphenadrineDesflurane may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
ParaldehydeDesflurane may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Desflurane is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
PramipexoleDesflurane may increase the sedative activities of Pramipexole.
RopiniroleDesflurane may increase the sedative activities of Ropinirole.
RotigotineDesflurane may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Desflurane.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
SuvorexantDesflurane may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
ThalidomideDesflurane may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZolpidemDesflurane may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food InteractionsNot Available

Targets

Kind
Protein group
Organism
Human
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Components:
NameUniProt IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3P28472 Details
Gamma-aminobutyric acid receptor subunit deltaO14764 Details
Gamma-aminobutyric acid receptor subunit epsilonP78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3Q99928 Details
Gamma-aminobutyric acid receptor subunit piO00591 Details
Gamma-aminobutyric acid receptor subunit thetaQ9UN88 Details
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
Human
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
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. Epub 2006 Sep 13. [PubMed:16973644 ]
Kind
Protein
Organism
Human
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 conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inacti...
Gene Name:
GRIA1
Uniprot ID:
P42261
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
Human
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:19903818). Contributes to the regulation of the membrane potential and nerve signaling, and prevents neuronal hyperexcitability (PubMed:17156368). Forms tetrameric potassium-selective channels through which ...
Gene Name:
KCNA1
Uniprot ID:
Q09470
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
Human
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.
Gene Name:
ATP2C1
Uniprot ID:
P98194
Molecular Weight:
100576.42 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 ]
Kind
Protein
Organism
Human
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 complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked toget...
Gene Name:
ATP5D
Uniprot ID:
P30049
Molecular Weight:
17489.755 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. 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
Human
Pharmacological action
unknown
Actions
unknown
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 transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND1
Uniprot ID:
P03886
Molecular Weight:
35660.055 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 ]

Carriers

Kind
Protein
Organism
Human
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 03, 2013 10:52