DIF

2-[2,6-DICHLOROPHENYL)AMINO]BENZENEACETIC ACID

Created: 2000-01-28
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count30
Chiral Atom Count0
Bond Count31
Aromatic Bond Count12
2D diagram of DIF
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Chemical Component Summary

Name2-[2,6-DICHLOROPHENYL)AMINO]BENZENEACETIC ACID
SynonymsDICLOFENAC
Systematic Name (OpenEye OEToolkits)2-[2-[(2,6-dichlorophenyl)amino]phenyl]ethanoic acid
FormulaC14 H11 Cl2 N O2
Molecular Weight296.149
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04Clc2cccc(Cl)c2Nc1ccccc1CC(=O)O
SMILESCACTVS3.341OC(=O)Cc1ccccc1Nc2c(Cl)cccc2Cl
SMILESOpenEye OEToolkits1.5.0c1ccc(c(c1)CC(=O)O)Nc2c(cccc2Cl)Cl
Canonical SMILESCACTVS3.341 OC(=O)Cc1ccccc1Nc2c(Cl)cccc2Cl
Canonical SMILESOpenEye OEToolkits1.5.0 c1ccc(c(c1)CC(=O)O)Nc2c(cccc2Cl)Cl
InChIInChI1.03 InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)
InChIKeyInChI1.03 DCOPUUMXTXDBNB-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00586 
NameDiclofenac
Groups
  • approved
  • vet_approved
DescriptionDiclofenac is a phenylacetic acid derivative and non-steroidal anti-inflammatory drug (NSAID).[label] NSAIDs inhibit cyclooxygenase (COX)-1 and-2 which are the enzyme responsible for producing prostaglandins (PGs). PGs contribute to inflammation and pain signalling. Diclofenac, like other NSAIDs, is often used as first line therapy for acute and chronic pain and inflammation from a variety of causes. Diclofenac was the product of rational drug design based on the structures of [phenylbutazone], [mefenamic acid], and [indomethacin].[A180796] The addition of two chlorine groups in the ortho position of the phenyl ring locks the ring in maximal torsion which appears to be related to increased potency. It is often used in combination with [misoprostol] to prevent NSAID-induced gastric ulcers. Diclofenac was first approved by the FDA in July 1988 under the trade name Voltaren, marketed by Novartis (previously Ciba-Geigy).[L7360]
Synonyms
  • Diclofenacum
  • Diclofenac sodium
  • Diclofenac deanol
  • Diclofenac epolamine
  • Diclofenac
Brand Names
  • Sunmark Arthritis Pain
  • Nuvya
  • Infla-eze
  • Diclosiacin
  • Salonpas
IndicationDiclofenac is indicated for use in the treatment of pain and inflammation from varying sources including inflammatory conditions such as osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis, as well as injury-related inflammation due to surgery and physical trauma. It is often used in combination with [misoprostol] as a gastro-protective agent in patients with high risk of developing NSAID-induced ulcers.
Categories
  • Acetic Acid Derivatives and Related Substances
  • Acids, Carbocyclic
  • Agents causing angioedema
  • Agents causing hyperkalemia
  • Agents that produce hypertension
ATC-Code
  • S01CC01
  • S01BC03
  • M01AB55
  • M02AA15
  • M01AB05
CAS number15307-86-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknownsubstrate
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
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 CHEMBL139
PubChem 3033
ChEMBL CHEMBL139
ChEBI CHEBI:47381
CCDC/CSD SIKLIH10, SIKLIH07, SIKLIH, GOGFOA, SIKLIH05, SIKLIH08, SIKLIH03, SIKLIH02, XUVQUB, BAHMUV, UMUZAE, SIKLIH09, SIKLIH01, OPOFUW, XUVQEL, GOGFOA01, GOGGAN01, XUVYAP01, XUVSIR, LULROC, DUBWEF, WABJAO, WABHOA01, SIKLIH12, WABHOA, NELJIB, WERLAK, WERLOY
COD 2300059, 2006253, 2006252, 4500096, 1517742