Diflunisal (CED0005867)

Record Information
Version1.0
Creation Date2009-07-21 20:27:51 UTC
Update Date2026-05-14 16:51:00 UTC
Accession NumberCHEM002292
Identification
Common NameDiflunisal
ClassSmall Molecule
Description
Diflunisal is an exogenous organic compound with the formula C13H8F2O3 and an average molecular weight of 250.20 g/mol. It exists as a solid at room temperature. Diflunisal belongs to the biphenyls and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This compound is used as a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is found in 18 recorded sources, including analgesics within healthcare, pharmaceuticals, and veterinary products; food preservation within food, food processing, and cookware; and various household cleaning and consumer products such as perfumes within detergents and soaps, ash trays, and non-electric simulated smoking devices. It is also associated with electrical and electronic equipment, including antennas, coils, conductors or conductive bodies characterized by the conductive materials, electrodes, and electrically stimulated smoking devices. The recorded exposure route is oral. Diflunisal has seven recorded protein targets: Prostaglandin G/H synthase 1 (PTGS1), Prostaglandin G/H synthase 2 (PTGS2), Transthyretin (TTR), Albumin (ALB), Carbonic anhydrase 1 (CA1), Carbonic anhydrase 2 (CA2), and Solute carrier family 22 member 6 (SLC22A6). While the precise mechanism of its analgesic and anti-inflammatory actions is not known, diflunisal is a prostaglandin synthetase inhibitor. Because prostaglandins are known to be among the mediators of inflammation and pain—and because they sensitize afferent nerves and potentiate the action of bradykinin in inducing pain in animals—the mode of action for diflunisal may be due to a decrease of prostaglandins in peripheral tissues.
Contaminant Type
  • Anti-Inflammatory Agent, Non-Steroidal
  • Cyclooxygenase Inhibitor
  • Drug
  • Ester
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
2',4'-Difluoro-4-hydroxy-3-biphenylcarboxylic acidChEBI
2-(Hydroxy)-5-(2,4-difluorophenyl)benzoic acidChEBI
5-(2,4-Difluorophenyl)salicylic acidChEBI
DolobidChEBI
2',4'-Difluoro-4-hydroxy-3-biphenylcarboxylateGenerator
2-(Hydroxy)-5-(2,4-difluorophenyl)benzoateGenerator
5-(2,4-Difluorophenyl)salicylateGenerator
Diflunisal novopharm brandHMDB
DolocidHMDB
Frosst sa brand OF diflunisalHMDB
Novopharm brand OF diflunisalHMDB
Nu pharm brand OF diflunisalHMDB
Nu-diflunisalHMDB
Merck brand OF diflunisalHMDB
Novo-diflunisalHMDB
Apo-diflunisalHMDB
DolobisHMDB
Merck sharp and dohme brand OF diflunisalHMDB
Nu-pharm brand OF diflunisalHMDB
Apotex brand OF diflunisalHMDB
Cahill may roberts brand OF diflunisalHMDB
Apo diflunisalHMDB
ApoDiflunisalHMDB
Novo diflunisalHMDB
Nu diflunisalHMDB
NovoDiflunisalHMDB
NuDiflunisalHMDB
Chemical FormulaC13H8F2O3
Average Molecular Mass250.198 g/mol
Monoisotopic Mass250.044 g/mol
CAS Registry Number22494-42-4
IUPAC Name5-(2,4-difluorophenyl)-2-hydroxybenzoic acid
Traditional Namediflunisal
SMILESOC(=O)C1=C(O)C=CC(=C1)C1=C(F)C=C(F)C=C1
InChI IdentifierInChI=1S/C13H8F2O3/c14-8-2-3-9(11(15)6-8)7-1-4-12(16)10(5-7)13(17)18/h1-6,16H,(H,17,18)
InChI KeyHUPFGZXOMWLGNK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fluorobenzene
  • Halobenzene
  • Phenol
  • Aryl fluoride
  • Aryl halide
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point210-211°C
Boiling PointNot Available
SolubilityPractically insoluble (14.5 mg/L) at neutral or acidic pH.
Predicted Properties
PropertyValueSource
Water Solubility0.071 g/LALOGPS
logP3.11ALOGPS
logP3.91ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.69ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.86 m³·mol⁻¹ChemAxon
Polarizability22.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0pc0-1190000000-37ea5d58644c01ef5b1eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05fr-5019000000-223530358c78521d8313Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-2690000000-64056c9dc4e2f14d3c59Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4j-5590000000-462ea99995ea9238bf94Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-5490000000-ec23e03578a95364b748Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9550000000-2fa065aea811fa7b6c5aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-9000000000-01d2c7c75ab3756b3df7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-e1009fb8e100faed2065Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0090000000-e9bcdf3ba0212ee28f45Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fc0-1970000000-baed3c5d64825d6b04b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-0090000000-6427bf95a0116aa621f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-83af00a8dd308410951dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0690000000-a756057c6442130830efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0090000000-645b3ae2575f11227813Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-78fd25facb031cdb643fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0940000000-9920437171fca6936f28Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-3e0ed3bddcaf7a500b10Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-0090000000-4ac100e6866826f4e00aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kdi-1930000000-6c51e381123d99125d70Not AvailableView Spectrum
MSMS Spectrumsplash10-0fai-1690000000-d231ff5a9ac7d9769d2dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of overdose include coma, tachycardia, stupor, and vomiting.
TreatmentIn the event of overdosage, the stomach should be emptied by inducing vomiting or by gastric lavage, and the patient carefully observed and given symptomatic and supportive treatment. Because of the high degree of protein binding, hemodialysis may not be effective. (2)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
392.0mg/kgNot AvailableRatLD50OralexperimentalA308
439.0mg/kgNot AvailableMouseLD50OralexperimentalA308
603.0mg/kgNot AvailableRabbitLD50OralexperimentalA308
521.0Log mg/kg[290:930]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
370AnalgesicsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)23.2769
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)20.8636
Click to view 3D structureHTH-type transcriptional regulator MgrAP0C1S0Staphylococcus aureusPredicted (SEA)0.389246
Click to view 3D structure2-Hydroxyacid oxidase 1Q9WU19Mus musculusPredicted (SEA)0.155698
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.544945
Stromal cell-derived factor 1 structureClick to view 3D structureStromal cell-derived factor 1P48061HumansPredicted (SEA)2.10193
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)3.97031
2-amino-3-carboxymuconate-6-semialdehyde decarboxylase structureClick to view 3D structure2-amino-3-carboxymuconate-6-semialdehyde decarboxylaseQ8TDX5HumansPredicted (SEA)0.155698
Albumin structureClick to view 3D structureAlbuminP02768HumansPredicted (SEA)18.2167
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)48.1887
Click to view 3D structureComplement factor DP32038Rattus norvegicusPredicted (SEA)1.40129
Dual specificity protein phosphatase 3 structureClick to view 3D structureDual specificity protein phosphatase 3P51452HumansPredicted (SEA)17.2047
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)26.5466
Hepatocyte nuclear factor 4-alpha structureClick to view 3D structureHepatocyte nuclear factor 4-alphaP41235HumansPredicted (SEA)3.26967
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)169.711
Tyrosine-protein phosphatase non-receptor type 11 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 11Q06124HumansPredicted (SEA)29.427
Hepatocyte nuclear factor 4-gamma structureClick to view 3D structureHepatocyte nuclear factor 4-gammaQ14541HumansPredicted (SEA)1.24559
Tyrosine-protein phosphatase non-receptor type 22 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 22Q9Y2R2HumansPredicted (SEA)11.366
Tyrosine-protein phosphatase non-receptor type 6 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 6P29350HumansPredicted (SEA)3.03612
Click to view 3D structureLow molecular weight protein-tyrosine phosphatase AP9WIA1Mycobacterium tuberculosisPredicted (SEA)2.95827
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)74.5017
Tyrosine-protein phosphatase non-receptor type 9 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 9P43378HumansPredicted (SEA)2.33548
Interleukin-4 structureClick to view 3D structureInterleukin-4P05112HumansPredicted (SEA)2.33548
Aldo-keto reductase family 1 member C2 structureClick to view 3D structureAldo-keto reductase family 1 member C2P52895HumansPredicted (SEA)37.679
Receptor-type tyrosine-protein phosphatase C structureClick to view 3D structureReceptor-type tyrosine-protein phosphatase CP08575HumansPredicted (SEA)5.83869
Albumin structureClick to view 3D structureAlbuminP02768HumansKnownThe precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues.
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansKnownThe precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues.
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansKnownNot Available
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansKnownNot Available
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansKnownThe precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues.
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansKnownThe precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues.
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00861
HMDB IDHMDB0014999
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB ID1FL
Wikipedia LinkDiflunisal
Chemspider ID2951
ChEBI ID39669
PubChem Compound ID3059
Kegg Compound IDC01691
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Ruyle, W.V., Jarett, L.H. and Matzuk, A.R. ; U S . Patent 3,714,226; January 30, 1973; assigned to Merck & Co., Inc.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23144359
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23416065
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217