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Identification
Name Desflurane
Accession Number DB01189 (APRD00907)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Desflurano [INN-Spanish]
Desfluranum [INN-Latin]
Salts Not Available
Brand names
Name Company
Suprane
Brand mixtures Not Available
Categories
  • Anesthetics, Inhalation
  • Neuroprotective Agents
CAS number 57041-67-5
Weight Average: 168.0378
Monoisotopic: 168.000983916
Chemical Formula C3H2F6O
InChI Key InChIKey=DPYMFVXJLLWWEU-UHFFFAOYSA-N
InChI
InChI=1S/C3H2F6O/c4-1(3(7,8)9)10-2(5)6/h1-2H
Plain Text
IUPAC Name
2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane
SMILES
FC(F)OC(F)C(F)(F)F
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Alkyl Halides
  • Ethers
Pharmacology
Indication For use as an inhalation agent for induction and/or maintenance of anesthesia for inpatient and outpatient surgery in adults.
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.
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
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Baxter healthcare corp anesthesia critical care
Packagers
Dosage forms
Form Route Strength
Liquid Respiratory (inhalation)
Prices
Unit description Cost Unit
Suprane inhalation liquid 0.76 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 5617906 1994-10-08 2014-10-08
Properties
State liquid
Experimental Properties
Property Value Source
boiling point 23.5 °C Not Available
water solubility Negligible Not Available
logP 1.9 Not Available
Predicted Properties
Property Value Source
water solubility 3.54e+00 g/l ALOGPS
logP 2.19 ALOGPS
logP 2.4 ChemAxon
logS -1.7 ALOGPS
pKa (strongest acidic) 18.87 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 9.23 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 18.12 ChemAxon
polarizability 7.89 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00546 Link_out
KEGG Compound C07519 Link_out
PubChem Compound 42113 Link_out
PubChem Substance 46505270 Link_out
ChemSpider 38403 Link_out
ChEBI 4445 Link_out
ChEMBL 4445 Link_out
Therapeutic Targets Database DAP000693 Link_out
PharmGKB PA164749136 Link_out
Drug Product Database 2227428 Link_out
RxList http://www.rxlist.com/cgi/generic2/desflurane.htm Link_out
Drugs.com http://www.drugs.com/cons/desflurane-inhalation-oral-nebulization.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Desflurane Link_out
ATC Codes
  • N01AB07
AHFS Codes
  • 28:04.00
PDB Entries Not Available
FDA label show (174 KB)
MSDS show (51.1 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Gamma-aminobutyric-acid receptor subunit alpha-1

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P14867 Link_out
Gene: GABRA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Seo K, Seino H, Yoshikawa H, Petrenko AB, Baba H, Fujiwara N, Someya G, Kawano Y, Maeda T, Matsuda M, Kanematsu T, Hirata M: Genetic reduction of GABA receptor gamma2 subunit expression potentiates the immobilizing action of isoflurane. Neurosci Lett. 2010 Mar 12;472(1):1-4. Epub 2010 Jan 25. Pubmed

2. Glycine receptor subunit alpha-1

Pharmacological action: yes
Actions: agonist

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)

Organism class: human
UniProt ID: P23415 Link_out
Gene: GLRA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists

Organism class: human
UniProt ID: P42261 Link_out
Gene: GRIA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inducer

Mediates the voltage-dependent potassium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a potassium-selective channel through which potassium ions may pass in accordance with their electrochemical gradient

Organism class: human
UniProt ID: Q09470 Link_out
Gene: KCNA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor

This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of the calcium

Organism class: human
UniProt ID: P98194 Link_out
Gene: ATP2C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 delta chain, mitochondrial

Pharmacological action: unknown
Actions: other/unknown

Produces ATP from ADP in the presence of a proton gradient across the membrane

Organism class: human
UniProt ID: P30049 Link_out
Gene: ATP5D Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: unknown
Organism class: human
UniProt ID: P03886 Link_out
Gene: MT-ND1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

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

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19