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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
SynonymLanguageCode
(+-)-2-Difluoromethyl 1,2,2,2-tetrafluoroethyl etherNot AvailableNot Available
1,1,1,2-Tetrafluoro-2-(difluoromethoxy)ethaneNot AvailableNot Available
DesfluraneNot AvailableNot Available
DesfluranoSpanishINN
DesfluranumLatinINN
Difluoromethyl 1,2,2,2-tetrafluoroethyl etherNot AvailableNot Available
SupraneNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
SupraneNot Available
Brand mixturesNot Available
Categories
CAS number57041-67-5
WeightAverage: 168.0378
Monoisotopic: 168.000983916
Chemical FormulaC3H2F6O
InChI KeyDPYMFVXJLLWWEU-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsEthers; Organofluorides; Alkyl Fluorides
Substituentsorganofluoride; organohalogen; alkyl halide; alkyl fluoride
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
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.
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
Property Value Probability
Human Intestinal Absorption + 0.9974
Blood Brain Barrier + 0.9941
Caco-2 permeable + 0.626
P-glycoprotein substrate Non-substrate 0.883
P-glycoprotein inhibitor I Non-inhibitor 0.9415
P-glycoprotein inhibitor II Non-inhibitor 0.9027
Renal organic cation transporter Non-inhibitor 0.9311
CYP450 2C9 substrate Non-substrate 0.8676
CYP450 2D6 substrate Non-substrate 0.919
CYP450 3A4 substrate Non-substrate 0.7556
CYP450 1A2 substrate Non-inhibitor 0.6194
CYP450 2C9 substrate Non-inhibitor 0.836
CYP450 2D6 substrate Non-inhibitor 0.9466
CYP450 2C19 substrate Non-inhibitor 0.707
CYP450 3A4 substrate Non-inhibitor 0.9604
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8921
Ames test Non AMES toxic 0.9042
Carcinogenicity Carcinogens 0.7045
Biodegradation Not ready biodegradable 0.9566
Rat acute toxicity 1.2690 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9724
hERG inhibition (predictor II) Non-inhibitor 0.909
Pharmacoeconomics
Manufacturers
  • Baxter healthcare corp anesthesia critical care
Packagers
Dosage forms
FormRouteStrength
LiquidRespiratory (inhalation)
Prices
Unit descriptionCostUnit
Suprane inhalation liquid0.76USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States56179061994-10-082014-10-08
Properties
Stateliquid
Experimental Properties
PropertyValueSource
boiling point23.5 °CNot Available
water solubilityNegligibleNot Available
logP1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.54ALOGPS
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
Spectra
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00546
KEGG CompoundC07519
PubChem Compound42113
PubChem Substance46505270
ChemSpider38403
ChEBI4445
ChEMBLCHEMBL1200733
Therapeutic Targets DatabaseDAP000693
PharmGKBPA164749136
Drug Product Database2227428
RxListhttp://www.rxlist.com/cgi/generic2/desflurane.htm
Drugs.comhttp://www.drugs.com/cons/desflurane-inhalation-oral-nebulization.html
WikipediaDesflurane
ATC CodesN01AB07
AHFS Codes
  • 28:04.00
PDB EntriesNot Available
FDA labelshow(174 KB)
MSDSshow(51.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. GABA-A receptor (anion channel)

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: positive allosteric modulator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4 P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6 Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1 P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2 P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3 P28472 Details
Gamma-aminobutyric acid receptor subunit delta O14764 Details
Gamma-aminobutyric acid receptor subunit epsilon P78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2 P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928 Details
Gamma-aminobutyric acid receptor subunit pi O00591 Details
Gamma-aminobutyric acid receptor subunit theta Q9UN88 Details

References:

  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. Pubmed
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. Epub 2008 Mar 31. Pubmed

2. Glycine receptor subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glycine receptor subunit alpha-1 P23415 Details

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
  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
  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

3. Glutamate receptor 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor 1 P42261 Details

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
  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
  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

4. Potassium voltage-gated channel subfamily A member 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Potassium voltage-gated channel subfamily A member 1 Q09470 Details

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
  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
  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. Pubmed

5. Calcium-transporting ATPase type 2C member 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Calcium-transporting ATPase type 2C member 1 P98194 Details

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
  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

6. ATP synthase subunit delta, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
ATP synthase subunit delta, mitochondrial P30049 Details

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
  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
  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

7. NADH-ubiquinone oxidoreductase chain 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: unknown

Components

Name UniProt ID Details
NADH-ubiquinone oxidoreductase chain 1 P03886 Details

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
  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

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

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

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Drug created on June 13, 2005 07:24 / Updated on December 03, 2013 10:52