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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:09:55 UTC
HMDB IDHMDB0014724
Secondary Accession Numbers
  • HMDB14724
Metabolite Identification
Common NameDiclofenac
DescriptionDiclofenac is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt. [PubChem]The antiinflammatory effects of diclofenac are believed to be due to inhibition of both leukocyte migration and the enzyme cylooxygenase (COX-1 and COX-2), leading to the peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, inhibition of their synthesis is responsible for the analgesic effects of diclofenac. Antipyretic effects may be due to action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat dissipation.
Structure
Thumb
Synonyms
ValueSource
2-((2,6-Dichlorophenyl)amino)benzeneacetic acidChEBI
[2-(2,6-dichloroanilino)Phenyl]acetic acidChEBI
Diclofenac acidChEBI
DiclofenacoChEBI
DiclofenacumChEBI
2-((2,6-Dichlorophenyl)amino)benzeneacetateGenerator
[2-(2,6-dichloroanilino)Phenyl]acetateGenerator
Diclofenac potassiumHMDB
ISV-205HMDB
NovapirinaMeSH
OrthofenMeSH
OrtofenMeSH
DichlofenalMeSH
Diclonate PMeSH
DicrofenacMeSH
FeloranMeSH
OrthophenMeSH
Sodium diclofenacMeSH
VoltarenMeSH
VoltarolMeSH
Diclofenac sodiumMeSH
DiclophenacMeSH
SR 38MeSH
Diclofenac, sodiumMeSH
SR-38MeSH
Chemical FormulaC14H11Cl2NO2
Average Molecular Weight296.149
Monoisotopic Molecular Weight295.016684015
IUPAC Name2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
Traditional Namediclofenac
CAS Registry Number15307-86-5
SMILES
OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl
InChI Identifier
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)
InChI KeyDCOPUUMXTXDBNB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • 1,3-dichlorobenzene
  • Aryl chloride
  • Aryl halide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Organochloride
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point283 - 285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0045 g/LNot Available
LogP3.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0045 g/LALOGPS
logP4.98ALOGPS
logP4.26ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.46 m³·mol⁻¹ChemAxon
Polarizability27.93 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xv-3390000000-cd724f772f8ff3648856View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xv-3390000000-cd724f772f8ff3648856View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4290000000-1eb3d1011ce45deff962View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-5090000000-00fc73f6f5cfbb7052d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-1d8a04523a99bbdd0f79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-55cf6c5663edc2bce2afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-0257da659c18c3020ebeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0w29-0090000000-eba79744370d30689f45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03fr-0890000000-0870dbb742038ce60ba1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-a9b9817f70b72a327169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-58aba74cf5c165b0b3e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-380ce6ec03fa880c2feeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0w29-0090000000-1c764b23643b9731a5a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0ik9-0290000000-5d59b6e5d4465a9e6493View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-483b1ac79bbfb8f591c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0fb9-0950000000-4192d5344ed223d4bfd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-1d8a04523a99bbdd0f79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0090000000-d28bb6688b1bce51bfceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-33332a8dbce37d5ad759View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1490000000-f1c9ca0a1b924dba188eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-4910000000-4c58f3f969da3d86e23cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00or-7900000000-3b2e03ec45a0b642cb4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0390000000-247401e4df8c88d9f260View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0090000000-a3ff3ed470584d694666View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-29ed9f5d1fb4bcf6262bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-4290000000-a381ef55b23a6901b44aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0090000000-00e8c59bbd02e8ef68e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0090000000-dae419eef17327b624d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kc6-4390000000-a037e01b7793bd48c1d5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03xv-1290000000-8fb3ce6f68fc69b5218eView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00586 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00586 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00586
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2925
KEGG Compound IDC01690
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiclofenac
METLIN IDNot Available
PubChem Compound3033
PDB IDDIF
ChEBI ID47381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. [PubMed:11496855 ]
  2. Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. [PubMed:11992745 ]
  3. Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. [PubMed:16645966 ]
  4. Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [PubMed:16740558 ]
  5. Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. [PubMed:16968830 ]
  6. Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. doi: 10.1185/03007995.2010.486301. [PubMed:20470236 ]
  7. Sigma Aldrich [Link]