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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-11-09 23:29:24 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
Data?1582753213
Synonyms
ValueSource
2-((2,6-Dichlorophenyl)amino)benzeneacetic acidChEBI
[2-(2,6-Dichloroanilino)phenyl]acetic acidChEBI
Diclofenac acidChEBI
DiclofenacoChEBI
DiclofenacumChEBI
Diclofenamic acidChEBI
SolarazeKegg
ZorvolexKegg
2-((2,6-Dichlorophenyl)amino)benzeneacetateGenerator
[2-(2,6-Dichloroanilino)phenyl]acetateGenerator
DiclofenamateGenerator
Diclofenac potassiumHMDB
ISV-205HMDB
NovapirinaHMDB
OrthofenHMDB
OrtofenHMDB
DichlofenalHMDB
Diclonate pHMDB
DicrofenacHMDB
FeloranHMDB
OrthophenHMDB
Sodium diclofenacHMDB
VoltarenHMDB
VoltarolHMDB
Diclofenac sodiumHMDB
DiclophenacHMDB
SR 38HMDB
Diclofenac, sodiumHMDB
SR-38HMDB
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
Description Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes 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 Molecular Properties
PropertyValueReference
Melting Point283 - 285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0045 g/LNot Available
LogP3.9Not Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M+H]+ExperimentalCBM157.730932474

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Diclofenac,1TMS,#12318.512https://arxiv.org/abs/1905.12712
Diclofenac,1TMS,#22336.9094https://arxiv.org/abs/1905.12712
Diclofenac,1TBDMS,#12562.4211https://arxiv.org/abs/1905.12712
Diclofenac,1TBDMS,#22579.9397https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xv-3390000000-cd724f772f8ff36488562017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xv-3390000000-cd724f772f8ff36488562018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4290000000-1eb3d1011ce45deff9622017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-5090000000-00fc73f6f5cfbb7052d02017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03xv-1290000000-8fb3ce6f68fc69b5218e2014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-1d8a04523a99bbdd0f792017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-55cf6c5663edc2bce2af2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-0257da659c18c3020ebe2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0w29-0090000000-eba79744370d30689f452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03fr-0890000000-0870dbb742038ce60ba12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-a9b9817f70b72a3271692017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-58aba74cf5c165b0b3e52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-380ce6ec03fa880c2fee2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0w29-0090000000-1c764b23643b9731a5a22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0ik9-0290000000-5d59b6e5d4465a9e64932017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-483b1ac79bbfb8f591c22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0fb9-0950000000-4192d5344ed223d4bfd62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-1d8a04523a99bbdd0f792017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0090000000-d28bb6688b1bce51bfce2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-33332a8dbce37d5ad7592017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1490000000-f1c9ca0a1b924dba188e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-4910000000-4c58f3f969da3d86e23c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00or-7900000000-3b2e03ec45a0b642cb4d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0390000000-247401e4df8c88d9f2602017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0090000000-a3ff3ed470584d6946662016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-29ed9f5d1fb4bcf6262b2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-4290000000-a381ef55b23a6901b44a2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0090000000-00e8c59bbd02e8ef68e72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0090000000-dae419eef17327b624d52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kc6-4390000000-a037e01b7793bd48c1d52016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00586 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00586 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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]