Tolmetin (CED0008746)

Record Information
Version1.0
Creation Date2016-05-25 18:20:49 UTC
Update Date2026-08-19 10:09:11 UTC
Accession NumberCHEM022121
Identification
Common NameTolmetin
ClassSmall Molecule
Description
Tolmetin is an organic compound with the chemical formula C15H15NO3 and an average molecular weight of 257.28 g/mol. Tolmetin belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. This compound is associated with 15 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is found in antiinflammatory and antirheumatic products as well as topical products for joint and muscular pain. In the category of food, food processing, and cookware, it is used in food preservation. It is also released from household cleaning and consumer products, including perfumes within detergents and soaps, pipe accessories, tobacco smoke filters, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, such as antennas, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, electrodes, hybrid capacitors, and two other sources. The recorded route of exposure for tolmetin is oral. Regarding its biological activity, the compound acts on two recorded protein targets, serving as an inhibitor of Prostaglandin G/H synthase 1 (PTGS1) and Prostaglandin G/H synthase 2 (PTGS2).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetic acidChEBI
1-Methyl-5-p-toluoylpyrrole-2-acetic acidChEBI
5-(p-Toluoyl)-1-methylpyrrole-2-acetic acidChEBI
TolmetinaChEBI
TolmetineChEBI
TolmetinoChEBI
TolmetinumChEBI
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetateGenerator
1-Methyl-5-p-toluoylpyrrole-2-acetateGenerator
5-(p-Toluoyl)-1-methylpyrrole-2-acetateGenerator
Anhydrous tolmetin sodiumHMDB
Sodium anhydrous, tolmetinHMDB
TolectinHMDB
Tolmetin sodiumHMDB
Anhydrous, tolmetin sodiumHMDB
Dihydrate tolmetin sodiumHMDB
Sodium, tolmetinHMDB
Tolmetin sodium anhydrousHMDB
Tolmetin sodium, anhydrousHMDB
Tolmetin sodium, dihydrateHMDB
Chemical FormulaC15H15NO3
Average Molecular Mass257.285 g/mol
Monoisotopic Mass257.105 g/mol
CAS Registry Number26171-23-3
IUPAC Name2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
Traditional Nametolmetin
SMILESCN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1
InChI IdentifierInChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
InChI KeyUPSPUYADGBWSHF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Benzoyl
  • Toluene
  • Monocyclic benzene moiety
  • N-methylpyrrole
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.81ALOGPS
logP2.73ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.39 m³·mol⁻¹ChemAxon
Polarizability27.67 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 Spectrumsplash10-014i-3930000000-6c43d7fafa7e68cf9c55Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-032i-9442000000-7726560133a119872ef9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-5053b1021a81c4668b54Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0910000000-7cb6eb9d5a42f35eb4bcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-9898c207cc31a596d319Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-6900000000-439955132bb3d3d37cf7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9200000000-aed48305fd97ea83af6dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-3399455ef4fbd98a64d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-0090000000-3838af75b0622946263bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0950000000-f1c503badfc8847c75e8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-6900000000-075fb92a19ab89905ba3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-5613b7d02b59ebbf2b1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-1290000000-494f40e70f911873c728Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006y-9730000000-49d63827f01b8620343fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-6a704ffbf3202179ae4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-8390000000-db73eded70ef5ae97453Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-5900000000-f83dcdc322966fec3da8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0190000000-71c82a0a228a88e32b6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066u-1890000000-018d899ab34427dfd79dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9720000000-7eec80edd3ab412a096dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
663.0Log mg/kg[370:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
363Antiinflammatory and antirheumatic productsHealthcare, pharmaceuticals & veterinary productsNot Available
364Topical products for joint and muscular painHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & 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
545Food PreservationFood, food processing & cookwareNot 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
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & 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
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)13.8572
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)7.47353
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)7.78492
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)12.6116
Interleukin-8 structureClick to view 3D structureInterleukin-8P10145HumansPredicted (SEA)2.49118
5'-3' exonuclease PLD3 structureClick to view 3D structure5'-3' exonuclease PLD3Q8IV08HumansPredicted (SEA)9.34191
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)383.33
Click to view 3D structureDehydrogenase/reductase SDR family member 9Q8VD48Rattus norvegicusPredicted (SEA)7.55137
Click to view 3D structureProstaglandin G/H synthase 2Q05769Mus musculusPredicted (SEA)86.1791
Aldo-keto reductase family 1 member C3 structureClick to view 3D structureAldo-keto reductase family 1 member C3P42330HumansPredicted (SEA)255.423
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)1024.34
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)483.599
Click to view 3D structureCytosolic carboxypeptidase 2Q5U5Z8HumansPredicted (SEA)8.87481
Click to view 3D structureStimulator of interferon genes proteinF1M391Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)333.895
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)2413.79
Sentrin-specific protease 7 structureClick to view 3D structureSentrin-specific protease 7Q9BQF6HumansPredicted (SEA)635.172
26S proteasome non-ATPase regulatory subunit 10 structureClick to view 3D structure26S proteasome non-ATPase regulatory subunit 10O75832HumansPredicted (SEA)21.9535
Click to view 3D structureGlucose-6-phosphate dehydrogenase-6-phosphogluconolactonaseQ9BHT9Plasmodium bergheiPredicted (SEA)215.487
Nuclear receptor subfamily 4immunitygroup A member 1 structureClick to view 3D structureNuclear receptor subfamily 4immunitygroup A member 1P22736HumansPredicted (SEA)93.6526
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)5128.24
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)2535.63
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)782.618
Click to view 3D structureProtein TatP04608Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)Predicted (SEA)236.739
Click to view 3D structureSentrin-specific protease 6Q9GZR1HumansPredicted (SEA)367.76
Concentrations
Not Available
External Links
DrugBank IDDB00500
HMDB IDHMDB0014643
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTolmetin
Chemspider ID5308
ChEBI ID71941
PubChem Compound ID5509
Kegg Compound IDC07149
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1206489
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19181568
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19505209
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20529813
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20582193
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20853464
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21936545
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22005020
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22943177
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23333829
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=3390998
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=445955
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6686452
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8472518