1FL

5-(2,4-DIFLUOROPHENYL)-2-HYDROXY-BENZOIC ACID

Created: 2005-07-26
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count26
Chiral Atom Count0
Bond Count27
Aromatic Bond Count13
2D diagram of 1FL

Chemical Component Summary

Name5-(2,4-DIFLUOROPHENYL)-2-HYDROXY-BENZOIC ACID
SynonymsDiflunisal
Systematic Name (OpenEye OEToolkits)5-(2,4-difluorophenyl)-2-hydroxy-benzoic acid
FormulaC13 H8 F2 O3
Molecular Weight250.198
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)c1cc(ccc1O)c2ccc(F)cc2F
SMILESCACTVS3.341OC(=O)c1cc(ccc1O)c2ccc(F)cc2F
SMILESOpenEye OEToolkits1.5.0c1cc(c(cc1c2ccc(cc2F)F)C(=O)O)O
Canonical SMILESCACTVS3.341 OC(=O)c1cc(ccc1O)c2ccc(F)cc2F
Canonical SMILESOpenEye OEToolkits1.5.0 c1cc(c(cc1c2ccc(cc2F)F)C(=O)O)O
InChIInChI1.03 InChI=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)
InChIKeyInChI1.03 HUPFGZXOMWLGNK-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00861 
NameDiflunisal
Groups
  • approved
  • investigational
DescriptionDiflunisal, a salicylate derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with pharmacologic actions similar to other prototypical NSAIAs. Diflunisal possesses anti-inflammatory, analgesic and antipyretic activity. Though its mechanism of action has not been clearly established, most of its actions appear to be associated with inhibition of prostaglandin synthesis via the arachidonic acid pathway. Diflunisal is used to relieve pain accompanied with inflammation and in the symptomatic treatment of rheumatoid arthritis and osteoarthritis.
Synonyms
  • 2-(hydroxy)-5-(2,4-difluorophenyl)benzoic acid
  • 2',4'-difluoro-4-hydroxy-3-biphenylcarboxylic acid
  • Diflunisalum
  • Diflunisal
  • 5-(2,4-difluorophenyl)salicylic acid
Brand Names
  • Diflunisal-250 - Tab 250mg
  • Nu-diflunisal Tab 500mg
  • Diflunisal-500 - Tab 500mg
  • Novo-diflunisal
  • Dolobid Tab 500mg
IndicationFor symptomatic treatment of mild to moderate pain accompanied by inflammation (e.g. musculoskeletal trauma, post-dental extraction, post-episiotomy), osteoarthritis, and rheumatoid arthritis.
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
ATC-CodeN02BA11
CAS number22494-42-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
UDP-glucuronosyltransferase 1-8MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...unknownsubstrate
UDP-glucuronosyltransferase 1-9MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...unknowninhibitor
TransthyretinMASHRLLLLCLAGLVFVSEAGPTGTGESKCPLMVKVLDAVRGSPAINVAV...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL898
PubChem 3059
ChEMBL CHEMBL898
ChEBI CHEBI:39669
CCDC/CSD FAFWIS02, OPOGAD, UWOKIC
COD 1517743