Tolfenamic acid (CHEM018301)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:08:27 UTC
Update Date2016-11-09 01:15:46 UTC
Accession NumberCHEM018301
Identification
Common NameTolfenamic acid
ClassSmall Molecule
DescriptionAn aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 3-chloro-2-methylphenyl group. Tolfenamic acid is used specifically for relieving the pain of migraine. It also shows anticancer activity.
Contaminant Sources
  • STOFF IDENT Compounds
  • Suspected Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Acide tolfenamiqueChEBI
Acido tolfenamicoChEBI
Acidum tolfenamicumChEBI
N-(2-Methyl-3-chlorophenyl)anthranilic acidChEBI
N-(3-Chloro-2-methylphenyl)anthranilic acidChEBI
N-(3-Chloro-O-tolyl)-anthranilic acidChEBI
N-(2-Methyl-3-chlorophenyl)anthranilateGenerator
N-(3-Chloro-2-methylphenyl)anthranilateGenerator
N-(3-Chloro-O-tolyl)-anthranilateGenerator
TolfenamateGenerator
ClotamHMDB
Pharmacia brand OF tolfenamic acidHMDB
RociclynHMDB
BifenacHMDB
N-(3-Chloro-O-tolyl)anthranilic acidHMDB
Provalis brand OF tolfenamic acidHMDB
Zambon brand OF tolfenamic acidHMDB
Chemical FormulaC14H12ClNO2
Average Molecular Mass261.704 g/mol
Monoisotopic Mass261.056 g/mol
CAS Registry Number13710-19-5
IUPAC Name2-[(3-chloro-2-methylphenyl)amino]benzoic acid
Traditional Nametolfenamic acid
SMILESCC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O
InChI IdentifierInChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18)
InChI KeyYEZNLOUZAIOMLT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Aminotoluene
  • Chlorobenzene
  • Halobenzene
  • Toluene
  • Aryl chloride
  • Aryl halide
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Secondary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organohalogen compound
  • Amine
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP4.64ALOGPS
logP5.49ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.65 m³·mol⁻¹ChemAxon
Polarizability26.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-029f-0290000000-193c55add3bbbb7d5121Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9354000000-172c43eaed1235f269a7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-1290000000-90928e5629bf0b4869e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a59-2790000000-175a0f838779d665e3dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-9e173e701dad784002bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02vl-0490000000-383bb531cf3b364e8551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3920000000-f62680abb4f65b264811Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0090000000-a116f61548e6965f47feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-d6c269ae6e8f165e1af8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l6-7970000000-7e83c63a8f674eb4dbb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-f1e193bda03b4aaed004Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2190000000-2fcbcc8f4250abae18ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-c2fa753da65a4bac80a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0090000000-d9fc45f2fd3466ad4bb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-8d746ea562322ef5c27aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0950000000-1f2515f699ddfef235a4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09216
HMDB IDHMDB0042043
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDTLF
Wikipedia LinkTolfenamic_acid
Chemspider ID530683
ChEBI ID32243
PubChem Compound ID610479
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20797618
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21392038
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21879384
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22213339
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22815231
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22954807
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23340327
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23576386
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23609055
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23620261
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23639209
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23661145
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23670891
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23686785
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23784084
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23811329
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23864386
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23874066
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23896517
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24030139
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24073394
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24104354
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24216474
24. Eslin D, Sankpal UT, Lee C, Sutphin RM, Maliakal P, Currier E, Sholler G, Khan M, Basha R: Tolfenamic acid inhibits neuroblastoma cell proliferation and induces apoptosis: a novel therapeutic agent for neuroblastoma. Mol Carcinog. 2013 May;52(5):377-86. doi: 10.1002/mc.21866. Epub 2011 Dec 28.
25. Chadalapaka G, Jutooru I, Sreevalsan S, Pathi S, Kim K, Chen C, Crose L, Linardic C, Safe S: Inhibition of rhabdomyosarcoma cell and tumor growth by targeting specificity protein (Sp) transcription factors. Int J Cancer. 2013 Feb 15;132(4):795-806. doi: 10.1002/ijc.27730. Epub 2012 Aug 3.
26. Sutphin RM, Connelly SF, Lee CM, Sankpal UT, Eslin D, Khan M, Pius H, Basha R: Anti-leukemic response of a NSAID, tolfenamic acid. Target Oncol. 2014 Jun;9(2):135-44. doi: 10.1007/s11523-013-0274-9. Epub 2013 Apr 23.
27. Subaiea GM, Adwan LI, Ahmed AH, Stevens KE, Zawia NH: Short-term treatment with tolfenamic acid improves cognitive functions in Alzheimer's disease mice. Neurobiol Aging. 2013 Oct;34(10):2421-30. doi: 10.1016/j.neurobiolaging.2013.04.002. Epub 2013 Apr 30.
28. Eslin D, Lee C, Sankpal UT, Maliakal P, Sutphin RM, Abraham L, Basha R: Anticancer activity of tolfenamic acid in medulloblastoma: a preclinical study. Tumour Biol. 2013 Oct;34(5):2781-9. doi: 10.1007/s13277-013-0836-6. Epub 2013 May 18.
29. Jeong JB, Yang X, Clark R, Choi J, Baek SJ, Lee SH: A mechanistic study of the proapoptotic effect of tolfenamic acid: involvement of NF-kappaB activation. Carcinogenesis. 2013 Oct;34(10):2350-60. doi: 10.1093/carcin/bgt224. Epub 2013 Jun 19.
30. Nadanaciva S, Aleo MD, Strock CJ, Stedman DB, Wang H, Will Y: Toxicity assessments of nonsteroidal anti-inflammatory drugs in isolated mitochondria, rat hepatocytes, and zebrafish show good concordance across chemical classes. Toxicol Appl Pharmacol. 2013 Oct 15;272(2):272-80. doi: 10.1016/j.taap.2013.06.019. Epub 2013 Jun 26.
31. Zhang X, Min KW, Liggett J, Baek SJ: Disruption of the transforming growth factor-beta pathway by tolfenamic acid via the ERK MAP kinase pathway. Carcinogenesis. 2013 Dec;34(12):2900-7. doi: 10.1093/carcin/bgt250. Epub 2013 Jul 16.
32. Kim HJ, Cho SD, Kim J, Kim SJ, Choi C, Kim JS, Nam JS, Han Kwon K, Kang KS, Jung JY: Apoptotic effect of tolfenamic acid on MDA-MB-231 breast cancer cells and xenograft tumors. J Clin Biochem Nutr. 2013 Jul;53(1):21-6. doi: 10.3164/jcbn.12-78. Epub 2013 Jun 29.
33. Jeong JB, Choi J, Baek SJ, Lee SH: Reactive oxygen species mediate tolfenamic acid-induced apoptosis in human colorectal cancer cells. Arch Biochem Biophys. 2013 Sep 15;537(2):168-75. doi: 10.1016/j.abb.2013.07.016. Epub 2013 Jul 26.