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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- 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
Structure for Desflurane (DB01189)
- 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
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Suprane Liquid 240 mL/240mL Respiratory (inhalation) Baxter Laboratories 1992-09-18 Not applicable US 
Suprane Liquid 100 % Respiratory (inhalation) Baxter Laboratories 1996-12-23 Not applicable Canada 
Suprane Liquid 1.5 g/1mL Respiratory (inhalation) Baxter Healthcare Corporation 2006-08-14 2006-08-14 US Suprane Liquid 240 mL/240mL Respiratory (inhalation) Baxter Laboratories 1992-09-18 Not applicable US Suprane Liquid 240 mL/240mL Respiratory (inhalation) General Injectables & Vaccines 2012-04-25 Not applicable US Suprane Liquid 240 mL/240mL Respiratory (inhalation) Baxter Laboratories 1992-09-18 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Desflurane Liquid 240 mL/240mL Respiratory (inhalation) Sandoz 2018-02-26 Not applicable US - International/Other Brands
- Suprane
- Categories
- UNII
- CRS35BZ94Q
- CAS number
- 57041-67-5
- Weight
- Average: 168.0378
Monoisotopic: 168.000983916 - Chemical Formula
- C3H2F6O
- 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
Pharmacology
- Indication
For use as an inhalation agent for induction and/or maintenance of anesthesia for inpatient and outpatient surgery in adults.
- Associated Therapies
- 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.
Target Actions Organism AGABA-A receptor (anion channel) positive allosteric modulatorHuman AGlycine receptor subunit alpha-1 agonistHuman AGlutamate receptor 1 antagonistHuman APotassium voltage-gated channel subfamily A member 1 inducerHuman ACalcium-transporting ATPase type 2C member 1 inhibitorHuman UATP synthase subunit delta, mitochondrial other/unknownHuman UNADH-ubiquinone oxidoreductase chain 1 unknownHuman - 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
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Voltage-dependent L-type calcium channel subunit alpha-1S --- Not Available c.3257G>A / c.520C>T ADR Inferred Malignant hyperthermia. Details Ryanodine receptor 1 --- Not Available c.103T>C / c.487C>T … show all ADR Inferred Malignant hyperthermia. Details
Interactions
- Drug Interactions
Drug Interaction 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Desflurane is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3,4-Methylenedioxyamphetamine The risk or severity of adverse effects can be increased when Desflurane is combined with 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when Desflurane is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when Desflurane is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of adverse effects can be increased when Desflurane is combined with 5-methoxy-N,N-dimethyltryptamine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Desflurane is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Desflurane is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Abexinostat The risk or severity of QTc prolongation can be increased when Desflurane is combined with Abexinostat. Acebutolol The risk or severity of QTc prolongation can be increased when Desflurane is combined with Acebutolol. Acepromazine The risk or severity of adverse effects can be increased when Desflurane is combined with Acepromazine. - Food Interactions
- Not Available
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
- External Links
- Human Metabolome Database
- HMDB0015320
- KEGG Drug
- D00546
- KEGG Compound
- C07519
- PubChem Compound
- 42113
- PubChem Substance
- 46505270
- ChemSpider
- 38403
- ChEBI
- 4445
- ChEMBL
- CHEMBL1200733
- Therapeutic Targets Database
- DAP000693
- PharmGKB
- PA164749136
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Desflurane
- ATC Codes
- N01AB07 — Desflurane
- AHFS Codes
- 28:04.16 — Inhalation Anesthetics
- FDA label
- Download (174 KB)
- MSDS
- Download (51.1 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Baxter International Inc.
- General Injectables and Vaccines Inc.
- Dosage forms
Form Route Strength Liquid Respiratory (inhalation) 1.5 g/1mL Liquid Respiratory (inhalation) 100 % Liquid Respiratory (inhalation) 240 mL/240mL - Prices
Unit description Cost Unit Suprane inhalation liquid 0.76USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5617906 No 1994-10-08 2014-10-08 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 23.5 °C Not Available water solubility Negligible Not Available logP 1.9 Not Available - Predicted Properties
Property Value Source Water Solubility 3.54 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 18.12 m3·mol-1 ChemAxon Polarizability 7.89 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.836 CYP450 2D6 inhibitor Non-inhibitor 0.9466 CYP450 2C19 inhibitor Non-inhibitor 0.707 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- 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
- Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Organofluoride / Alkyl halide / Alkyl fluoride / Aliphatic acyclic compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- organofluorine compound (CHEBI:4445)
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...
Components:
References
- Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090]
- 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
- Uniprot Name
- Glycine receptor subunit alpha-1
- Molecular Weight
- 52623.35 Da
References
- 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]
- 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]
- 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 co...
- Gene Name
- GRIA1
- Uniprot ID
- P42261
- Uniprot Name
- Glutamate receptor 1
- Molecular Weight
- 101505.245 Da
References
- 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]
- 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]
- 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:1990381...
- Gene Name
- KCNA1
- Uniprot ID
- Q09470
- Uniprot Name
- Potassium voltage-gated channel subfamily A member 1
- Molecular Weight
- 56465.01 Da
References
- 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]
- 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]
- 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
- Uniprot Name
- Calcium-transporting ATPase type 2C member 1
- Molecular Weight
- 100576.42 Da
References
- 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]
- 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 comp...
- Gene Name
- ATP5D
- Uniprot ID
- P30049
- Uniprot Name
- ATP synthase subunit delta, mitochondrial
- Molecular Weight
- 17489.755 Da
References
- 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]
- 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]
- 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 tra...
- Gene Name
- MT-ND1
- Uniprot ID
- P03886
- Uniprot Name
- NADH-ubiquinone oxidoreductase chain 1
- Molecular Weight
- 35660.055 Da
References
- 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]
- 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 colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- 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 November 12, 2018 07:28