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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12ClNO2
Molecular Weight 261.704
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLFENAMIC ACID

SMILES

CC1=C(Cl)C=CC=C1NC2=C(C=CC=C2)C(O)=O

InChI

InChIKey=YEZNLOUZAIOMLT-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Tolfenamic acid is a selective COX-2 inhibitor, which was marketed in Europe for the treatment of acute migraine disorders. Tolfenamic acid is currently unavailable for human use, however, it may be prescribed for veterinary purposes.

CNS Activity

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin G/H synthase 2
48
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CLOTAM

Approved Use

Acute migraine.

Launch Date

8.6192639E11
PubMed

PubMed

TitleDatePubMed
Human pharmacokinetics of tolfenamic acid, a new anti-inflammatory agent.
1981
A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells.
1999 Nov
[Effectiveness of tolfenamic acid in the prevention of migraine].
2002
Migraine headache.
2003 Dec
Determination of acidic drugs in sewage water by gas chromatography-mass spectrometry as tert.-butyldimethylsilyl derivatives.
2003 Jan 24
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.
2003 Jun 2
[Neurotransmitter mechanism of the tropoxin effect in comparison with other antimigraine preparations].
2003 May-Jun
Binuclear copper(II) complexes of tolfenamic: synthesis, crystal structure, spectroscopy and superoxide dismutase activity.
2004 Feb
Nitric oxide releasing derivatives of tolfenamic acid with anti-inflammatory activity and safe gastrointestinal profile.
2005 Dec 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Involvement of opioidergic and alpha2-adrenergic mechanisms in the central analgesic effects of non-steroidal anti-inflammatory drugs in sheep.
2006 Apr
Multi-residue determination of non-steroidal anti-inflammatory drug residues in animal serum and plasma by HPLC and photo-diode array detection.
2006 Nov-Dec
The use of combination therapies in the acute management of migraine.
2006 Sep
Rapid method for the determination of non-steroidal anti-inflammatory drugs in animal tissue by liquid chromatography-mass spectrometry with ion-trap detector.
2007 Mar 14
Current migraine management - patient acceptability and future approaches.
2008 Dec
ESE-1/EGR-1 pathway plays a role in tolfenamic acid-induced apoptosis in colorectal cancer cells.
2008 Dec
catena-Poly[[bis-[2-(2,3-dimethyl-anilino)benzoato-κO]cadmium(II)]-di-μ-3-pyridylmethanol-κN:O;κO:N].
2008 Feb 6
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.
2008 Oct
Assessment of the duration of the pain response associated with lameness in dairy cows, and the influence of treatment.
2008 Oct
Poloxamer 407 as a solubilising agent for tolfenamic acid and as a base for a gel formulation.
2008 Sep 2
Investigating AP-2 and YY1 protein expression as a cause of high HER2 gene transcription in breast cancers with discordant HER2 gene amplification.
2009
Regulation of HIV-1 transcription in cells of the monocyte-macrophage lineage.
2009 Dec 23
Thermodynamic and structural study of tolfenamic acid polymorphs.
2009 Dec 5
Tolfenamic acid inhibits esophageal cancer through repression of specificity proteins and c-Met.
2009 Jul
Confirmatory analysis of non-steroidal anti-inflammatory drugs in bovine milk by high-performance liquid chromatography with fluorescence detection.
2010 Apr 23
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Combined treatment of pancreatic cancer with mithramycin A and tolfenamic acid promotes Sp1 degradation and synergistic antitumor activity.
2010 Feb 1
Apoptotic Effect of Tolfenamic Acid in KB Human Oral Cancer Cells: Possible Involvement of the p38 MAPK Pathway.
2010 Jul
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.
2010 Jul
Occurrence and risk assessment of acidic pharmaceuticals in the Yellow River, Hai River and Liao River of north China.
2010 Jul 15
Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori.
2010 Mar 21
Novel milk-based oral formulations: proof of concept.
2010 May 10
Postoperative analgesic efficacy of meloxicam compared to tolfenamic acid in cats undergoing orthopaedic surgery.
2010 Oct
Activating transcription factor 2 (ATF2) controls tolfenamic acid-induced ATF3 expression via MAP kinase pathways.
2010 Sep 16
Effect of preventive (beta blocker) treatment, behavioural migraine management, or their combination on outcomes of optimised acute treatment in frequent migraine: randomised controlled trial.
2010 Sep 29
Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol.
2011 May 30
Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers.
2013 Feb 25
Tolfenamic acid downregulates BACE1 and protects against lead-induced upregulation of Alzheimer's disease related biomarkers.
2014 Apr
Patents

Patents

JP2003515526A
462

Sample Use Guides

In Vivo Use Guide
Take 200mg when the first symptoms of migraine appear. The treatment can be repeated once after 1-2 hours if a satisfactory response is not obtained.
Route of Administration: Oral
In Vitro Use Guide
Polymorphonuclear leukocytes were treated with tolfenamic acid at concentrations from 1 uM to 1000 uM and the compound inhibited LTB4-induced chemotaxis with IC50 value of 59 uM. Tolfenamic acid inhibited also FMLP-induced chemotaxis at the same concentration range (IC50 value was 46 uM).
Name Type Language
TOLFENAMIC ACID
EP   INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
Tolfenamic acid [WHO-DD]
Common Name English
2-((3-CHLORO-2-METHYLPHENYL)AMINO)BENZOIC ACID
Systematic Name English
TOLFENAMIC ACID [EP IMPURITY]
Common Name English
NSC-757873
Code English
TOLFENAMIC ACID [MI]
Common Name English
TOLFENAMIC ACID [MART.]
Common Name English
TOLFENAMIC ACID [EP MONOGRAPH]
Common Name English
N-(3-CHLORO-O-TOLYL)ANTHRANILIC
Common Name English
tolfenamic acid [INN]
Common Name English
TOLFENAMIC ACID [JAN]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1614
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
WHO-VATC QM01AG02
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
NCI_THESAURUS C257
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
WHO-ATC M01AG02
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
FDA ORPHAN DRUG 517816
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
FDA ORPHAN DRUG 517916
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
Code System Code Type Description
INN
2926
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
RXCUI
38377
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY RxNorm
IUPHAR
8769
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
MESH
C009500
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID1045409
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
FDA UNII
3G943U18KM
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
CAS
13710-19-5
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
DRUG CENTRAL
2698
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
CHEBI
32243
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
PUBCHEM
610479
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
MERCK INDEX
m10943
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY Merck Index
SMS_ID
100000077754
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
237-264-3
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
ChEMBL
CHEMBL121626
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
EVMPD
SUB11155MIG
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
NSC
757873
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
WIKIPEDIA
Tolfenamic acid
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
NCI_THESAURUS
C87328
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
DRUG BANK
DB09216
Created by admin on Sat Dec 16 15:54:35 UTC 2023 , Edited by admin on Sat Dec 16 15:54:35 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of TOLFENAMIC ACID
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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