Home Halogens 2-[(3-chloro-2-methylphenyl)amino]benzoic acid

2-[(3-chloro-2-methylphenyl)amino]benzoic acid

CAS No.:
13710-19-5
Catalog Number:
AG003SAR
Molecular Formula:
C14H12ClNO2
Molecular Weight:
261.7036
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%
In Stock USA
United States
$13
- +
5g
98%
In Stock USA
United States
$19
- +
25g
98%
In Stock USA
United States
$57
- +
Product Description
Catalog Number:
AG003SAR
Chemical Name:
2-[(3-chloro-2-methylphenyl)amino]benzoic acid
CAS Number:
13710-19-5
Molecular Formula:
C14H12ClNO2
Molecular Weight:
261.7036
MDL Number:
MFCD00133865
IUPAC Name:
2-(3-chloro-2-methylanilino)benzoic acid
InChI:
InChI=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 Key:
YEZNLOUZAIOMLT-UHFFFAOYSA-N
SMILES:
OC(=O)c1ccccc1Nc1cccc(c1C)Cl
EC Number:
237-264-3
UNII:
3G943U18KM
NSC Number:
757873
Properties
Complexity:
298  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
261.056g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
261.705g/mol
Monoisotopic Mass:
261.056g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
49.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.2  
Literature
Title Journal
Tolfenamic acid downregulates BACE1 and protects against lead-induced upregulation of Alzheimer's disease related biomarkers. Neuropharmacology 20140401
Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers. Chemico-biological interactions 20130225
Small molecule tolfenamic acid inhibits PC-3 cell proliferation and invasion in vitro, and tumor growth in orthotopic mouse model for prostate cancer. The Prostate 20121101
Simultaneous determination of mefenamic and tolfenamic acids in real samples by terbium-sensitized luminescence. Journal of fluorescence 20121101
Structure-activity relationship of fenamates as Slo2.1 channel activators. Molecular pharmacology 20121101
Raman and IR spectroscopic studies of fenamates--conformational differences in polymorphs of flufenamic acid, mefenamic acid and tolfenamic acid. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20121001
Tolfenamic acid suppresses cytochrome P450 2E1 expression in mouse liver. Integrative biology : quantitative biosciences from nano to macro 20120921
Development and validation of two multiresidue liquid chromatography tandem mass spectrometry methods based on a versatile extraction procedure for isolating non-steroidal anti-inflammatory drugs from bovine milk and muscle tissue. Analytical and bioanalytical chemistry 20120901
Determination of non-steroidal anti-inflammatory drugs and their metabolites in milk by liquid chromatography-tandem mass spectrometry. Analytical and bioanalytical chemistry 20120701
Structural features of mono- and tri-nuclear Zn(II) complexes with a non-steroidal anti-inflammatory drug as ligand. Dalton transactions (Cambridge, England : 2003) 20120621
Chemopreventive effects of tolfenamic acid against esophageal tumorigenesis in rats. Investigational new drugs 20120601
Italian guidelines for primary headaches: 2012 revised version. The journal of headache and pain 20120501
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis. Journal of natural products 20120427
Evaluating the effects of 14-day oral vedaprofen and tolfenamic acid treatment on renal function, hematological and biochemical profiles in healthy cats. Journal of veterinary pharmacology and therapeutics 20120201
Polymorph formation and nucleation mechanism of tolfenamic acid in solution: an investigation of pre-nucleation solute association. Pharmaceutical research 20120201
Cobalt(II) complexes with non-steroidal anti-inflammatory drug tolfenamic acid: Structure and biological evaluation. European journal of medicinal chemistry 20120201
Activating transcription factor 3 and the nervous system. Frontiers in molecular neuroscience 20120101
Tolfenamic acid induces apoptosis and growth inhibition in head and neck cancer: involvement of NAG-1 expression. PloS one 20120101
Effect of tolfenamic acid on canine cancer cell proliferation, specificity protein (sp) transcription factors, and sp-regulated proteins in canine osteosarcoma, mammary carcinoma, and melanoma cells. Journal of veterinary internal medicine 20120101
Modulation of the activity of Sp transcription factors by mithramycin analogues as a new strategy for treatment of metastatic prostate cancer. PloS one 20120101
Expression of specificity protein transcription factors in pancreatic cancer and their association in prognosis and therapy. Current medicinal chemistry 20120101
Anti-inflammatory drugs and prediction of new structures by comparative analysis. Anti-inflammatory & anti-allergy agents in medicinal chemistry 20120101
9,10-phenanthrenequinone induces monocytic differentiation of U937 cells through regulating expression of aldo-keto reductase 1C3. Biological & pharmaceutical bulletin 20120101
The ability of tolfenamic acid to penetrate the brain: a model for testing the brain disposition of candidate Alzheimer's drugs using multiple platforms. Current Alzheimer research 20111201
Interplay between molecular conformation and intermolecular interactions in conformational polymorphism: a molecular perspective from electronic calculations of tolfenamic acid. International journal of pharmaceutics 20111014
Nonsteroidal anti-inflammatory drug flufenamic acid is a potent activator of AMP-activated protein kinase. The Journal of pharmacology and experimental therapeutics 20111001
Development and validation of a confirmatory method for the determination of 12 non steroidal anti-inflammatory drugs in milk using liquid chromatography-tandem mass spectrometry. Journal of chromatography. A 20110916
Pharmacokinetic and pharmacodynamic modelling of marbofloxacin administered alone and in combination with tolfenamic acid in calves. Journal of veterinary pharmacology and therapeutics 20110801
Optimization of the derivatization reaction and the solid-phase microextraction conditions using a D-optimal design and three-way calibration in the determination of non-steroidal anti-inflammatory drugs in bovine milk by gas chromatography-mass spectrometry. Journal of chromatography. A 20110715
Inhibition of myeloid cell leukemia-1 by tolfenamic acid induces apoptosis in mucoepidermoid carcinoma. Oral diseases 20110701
Tolfenamic acid inhibits ovarian cancer cell growth and decreases the expression of c-Met and survivin through suppressing specificity protein transcription factors. Gynecologic oncology 20110701
Tolfenamic acid interrupts the de novo synthesis of the β-amyloid precursor protein and lowers amyloid beta via a transcriptional pathway. Current Alzheimer research 20110601
Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol. Chemico-biological interactions 20110530
Apoptotic effect of tolfenamic acid in androgen receptor-independent prostate cancer cell and xenograft tumor through specificity protein 1. Cancer science 20110401
Combined treatment of pancreatic cancer with mithramycin a and tolfenamic Acid promotes sp1 degradation and synergistic antitumor activity--letter. Cancer research 20110401
Chemopreventive effect of tolfenamic acid on KB human cervical cancer cells and tumor xenograft by downregulating specificity protein 1. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20110301
Tolfenamic acid decreases c-Met expression through Sp proteins degradation and inhibits lung cancer cells growth and tumor formation in orthotopic mice. Investigational new drugs 20110201
Therapeutic applications of NSAIDS in cancer: special emphasis on tolfenamic acid. Frontiers in bioscience (Scholar edition) 20110101
Congenital Pelger-Huët anomaly in a Danish/Swedish Farmdog: case report. Acta veterinaria Scandinavica 20110101
Combined analgesics in (headache) pain therapy: shotgun approach or precise multi-target therapeutics? BMC neurology 20110101
Betulinic acid inhibits colon cancer cell and tumor growth and induces proteasome-dependent and -independent downregulation of specificity proteins (Sp) transcription factors. BMC cancer 20110101
Enhanced anticancer activity of gemcitabine in combination with noscapine via antiangiogenic and apoptotic pathway against non-small cell lung cancer. PloS one 20110101
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. Healthcare informatics research 20101201
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
Postoperative analgesic efficacy of meloxicam compared to tolfenamic acid in cats undergoing orthopaedic surgery. The Journal of small animal practice 20101001
Activating transcription factor 2 (ATF2) controls tolfenamic acid-induced ATF3 expression via MAP kinase pathways. Oncogene 20100916
Occurrence and risk assessment of acidic pharmaceuticals in the Yellow River, Hai River and Liao River of north China. The Science of the total environment 20100715
Analytical strategy for the determination of non-steroidal anti-inflammatory drugs in plasma and improved analytical strategy for the determination of authorized and non-authorized non-steroidal anti-inflammatory drugs in milk by LC-MS/MS. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20100701
Apoptotic Effect of Tolfenamic Acid in KB Human Oral Cancer Cells: Possible Involvement of the p38 MAPK Pathway. Journal of clinical biochemistry and nutrition 20100701
Novel milk-based oral formulations: proof of concept. International journal of pharmaceutics 20100510
Pharmacokinetic and pharmacodynamic modelling of marbofloxacin administered alone and in combination with tolfenamic acid in goats. Veterinary journal (London, England : 1997) 20100501
Confirmatory analysis of non-steroidal anti-inflammatory drugs in bovine milk by high-performance liquid chromatography with fluorescence detection. Journal of chromatography. A 20100423
Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori. Dalton transactions (Cambridge, England : 2003) 20100321
Combined treatment of pancreatic cancer with mithramycin A and tolfenamic acid promotes Sp1 degradation and synergistic antitumor activity. Cancer research 20100201
Effect of preventive (beta blocker) treatment, behavioural migraine management, or their combination on outcomes of optimised acute treatment in frequent migraine: randomised controlled trial. BMJ (Clinical research ed.) 20100101
Thermodynamic and structural study of tolfenamic acid polymorphs. Journal of pharmaceutical and biomedical analysis 20091205
Development of a rapid, multi-class method for the confirmatory analysis of anti-inflammatory drugs in bovine milk using liquid chromatography tandem mass spectrometry. Journal of chromatography. A 20091113
Eicosanoids influence insect susceptibility to nucleopolyhedroviruses. Journal of invertebrate pathology 20091101
Tolfenamic acid inhibits esophageal cancer through repression of specificity proteins and c-Met. Carcinogenesis 20090701
Anti-inflammatory, antiproliferative, and radical-scavenging activities of tolfenamic acid and its metal complexes. Chemistry & biodiversity 20090601
The nonsteroidal anti-inflammatory drug tolfenamic acid inhibits BT474 and SKBR3 breast cancer cell and tumor growth by repressing erbB2 expression. Molecular cancer therapeutics 20090501
The relationship between diphenylamine structure and NSAIDs-induced hepatocytes injury. Toxicology letters 20090425
Polymer-induced heteronucleation of tolfenamic acid: structural investigation of a pentamorph. Journal of the American Chemical Society 20090408
Tolfenamic acid enhances pancreatic cancer cell and tumor response to radiation therapy by inhibiting survivin protein expression. Molecular cancer therapeutics 20090301
Thermodynamics of lipophilic drug binding to intestinal fatty acid binding protein and permeation across membranes. Molecular pharmaceutics 20090101
Investigating AP-2 and YY1 protein expression as a cause of high HER2 gene transcription in breast cancers with discordant HER2 gene amplification. Breast cancer research : BCR 20090101
Regulation of HIV-1 transcription in cells of the monocyte-macrophage lineage. Retrovirology 20090101
ESE-1/EGR-1 pathway plays a role in tolfenamic acid-induced apoptosis in colorectal cancer cells. Molecular cancer therapeutics 20081201
Current migraine management - patient acceptability and future approaches. Neuropsychiatric disease and treatment 20081201
Efficacy of tolfenamic acid and meloxicam in the control of postoperative pain following ovariohysterectomy in the cat. Veterinary anaesthesia and analgesia 20081101
Assessment of the duration of the pain response associated with lameness in dairy cows, and the influence of treatment. New Zealand veterinary journal 20081001
Optimizing prophylactic treatment of migraine: Subtypes and patient matching. Therapeutics and clinical risk management 20081001
Poloxamer 407 as a solubilising agent for tolfenamic acid and as a base for a gel formulation. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20080902
Effects of meloxicam or tolfenamic acid administration on the pain and stress responses of Merino lambs to mulesing. Australian veterinary journal 20080801
In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions. Basic & clinical pharmacology & toxicology 20080801
Effects of fenamate on inhibitory postsynaptic currents in Purkinje's cells. Bulletin of experimental biology and medicine 20080501
catena-Poly[[bis-[2-(2,3-dimethyl-anilino)benzoato-κO]cadmium(II)]-di-μ-3-pyridylmethanol-κN:O;κO:N]. Acta crystallographica. Section E, Structure reports online 20080301
The effect of suspended particles coated by humic acid on the toxicity of pharmaceuticals, estrogens, and phenolic compounds. Environment international 20080201
Confirmatory identification of sixteen non-steroidal anti-inflammatory drug residues in raw milk by liquid chromatography coupled with ion trap mass spectrometry. Rapid communications in mass spectrometry : RCM 20080101
Field evaluation of the efficacy of tolfenamic acid administered in one single preoperative injection for the prevention of postoperative pain in the dog. Journal of veterinary pharmacology and therapeutics 20071201
Inhibition of human thiopurine S-methyltransferase by various nonsteroidal anti-inflammatory drugs in vitro: a mechanism for possible drug interactions. Drug metabolism and disposition: the biological fate of chemicals 20070901
Tolfenamic acid is a potent CYP1A2 inhibitor in vitro but does not interact in vivo: correction for protein binding is needed for data interpretation. European journal of clinical pharmacology 20070901
Nonsteroidal anti-inflammatory drugs in cats: a review. Veterinary anaesthesia and analgesia 20070701
Eicosanoid biosynthesis inhibitors increase the susceptibility of Lymantria dispar to nucleopolyhedrovirus LdMNPV. Journal of invertebrate pathology 20070601
Acute migraine: Current treatment and emerging therapies. Therapeutics and clinical risk management 20070601
Regulation of vascular endothelial growth factor receptor-1 expression by specificity proteins 1, 3, and 4 in pancreatic cancer cells. Cancer research 20070401
Structure-based inhibitor design for an enzyme that binds different steroids: a potent inhibitor for human type 5 17beta-hydroxysteroid dehydrogenase. The Journal of biological chemistry 20070316
Rapid method for the determination of non-steroidal anti-inflammatory drugs in animal tissue by liquid chromatography-mass spectrometry with ion-trap detector. Analytica chimica acta 20070314
Characterization and physical stability of tolfenamic acid-PVP K30 solid dispersions. Pharmaceutical development and technology 20070101
The use of combination therapies in the acute management of migraine. Neuropsychiatric disease and treatment 20060901
Nutraceutical inhibitors of urokinase: potential applications in prostate cancer prevention and treatment. Oncology reports 20060801
Tolfenamic acid and pancreatic cancer growth, angiogenesis, and Sp protein degradation. Journal of the National Cancer Institute 20060621
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Involvement of opioidergic and alpha2-adrenergic mechanisms in the central analgesic effects of non-steroidal anti-inflammatory drugs in sheep. Research in veterinary science 20060401
Pharmacokinetic and pharmacodynamic interactions of tolfenamic acid and marbofloxacin in goats. Research in veterinary science 20060201
Determination of fourteen non-steroidal anti-inflammatory drugs in animal serum and plasma by liquid chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM 20060101
Multi-residue determination of non-steroidal anti-inflammatory drug residues in animal serum and plasma by HPLC and photo-diode array detection. Journal of chromatographic science 20060101
Interventions for preventing or treating alcohol hangover: systematic review of randomised controlled trials. BMJ (Clinical research ed.) 20051224
Nitric oxide releasing derivatives of tolfenamic acid with anti-inflammatory activity and safe gastrointestinal profile. Bioorganic & medicinal chemistry 20051201
Study of structural features and thermodynamic parameters, determining the chromatographic behaviour of drug-cyclodextrin complexes. Journal of chromatography. A 20050916
Prediction of genotoxicity of chemical compounds by statistical learning methods. Chemical research in toxicology 20050601
Geriatric pharmacology. The Veterinary clinics of North America. Small animal practice 20050501
Infrared studies of the polymorphic states of the fenamates. Journal of pharmaceutical and biomedical analysis 20050309
Influence of marbofloxacin on the pharmacokinetics and pharmacodynamics of tolfenamic acid in calves. Journal of veterinary pharmacology and therapeutics 20050201
PK-PD integration and PK-PD modelling of nonsteroidal anti-inflammatory drugs: principles and applications in veterinary pharmacology. Journal of veterinary pharmacology and therapeutics 20041201
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors. The Journal of pharmacology and experimental therapeutics 20041101
Pain management in cats--past, present and future. Part 2. Treatment of pain--clinical pharmacology. Journal of feline medicine and surgery 20041001
Synthesis and pharmacological evaluation of amide conjugates of NSAIDs with L-cysteine ethyl ester, combining potent antiinflammatory and antioxidant properties with significantly reduced gastrointestinal toxicity. Bioorganic & medicinal chemistry letters 20040716
Attitudes and concerns of French veterinarians towards pain and analgesia in dogs and cats. Veterinary anaesthesia and analgesia 20040701
Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. American journal of veterinary research 20040601
Migraine headache. Clinical evidence 20040601
Binuclear copper(II) complexes of tolfenamic: synthesis, crystal structure, spectroscopy and superoxide dismutase activity. Journal of inorganic biochemistry 20040201
Acute treatment of migraine. Breaking the paradigm of monotherapy. BMC neurology 20040101
Rizatriptan versus rizatriptan plus rofecoxib versus rizatriptan plus tolfenamic acid in the acute treatment of migraine. BMC neurology 20040101
Multi-residue liquid chromatography/tandem mass spectrometry method for the detection of non-steroidal anti-inflammatory drugs in bovine muscle: optimisation of ion trap parameters. Rapid communications in mass spectrometry : RCM 20040101
Migraine headache. Clinical evidence 20031201
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study. British journal of cancer 20030602
Determination of acidic drugs in sewage water by gas chromatography-mass spectrometry as tert.-butyldimethylsilyl derivatives. Journal of chromatography. A 20030124
[Neurotransmitter mechanism of the tropoxin effect in comparison with other antimigraine preparations]. Eksperimental'naia i klinicheskaia farmakologiia 20030101
[Effectiveness of tolfenamic acid in the prevention of migraine]. Medicina (Kaunas, Lithuania) 20020101
Search of antimicrobial activity of selected non-antibiotic drugs. Acta poloniae pharmaceutica 20020101
Intercalation and controlled release of pharmaceutically active compounds from a layered double hydroxide. Chemical communications (Cambridge, England) 20011121
Fenamates stimulate BKCa channel osteoblast-like MG-63 cells activity in the human. Journal of investigative medicine : the official publication of the American Federation for Clinical Research 20011101
Dexamethasone decreases migraine recurrence observed after treatment with a triptan combined with a nonsteroidal anti-inflammatory drug. Arquivos de neuro-psiquiatria 20010901
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. Journal of analytical toxicology 20010101
A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells. Endocrinology 19991101
Human pharmacokinetics of tolfenamic acid, a new anti-inflammatory agent. European journal of clinical pharmacology 19810101
Properties