TOLFENAMIC ACID

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 Search

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

Molecular Formula	C14H12ClNO2
Molecular Weight	261.704
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16005916 | https://www.medicines.org.uk/emc/medicine/449

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

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 2 51 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16005916	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute migraine 7 Sources: https://www.medicines.org.uk/emc/medicine/449	Primary		Approved 8583	CLOTAM Approved Use Acute migraine. Launch Date 1997

C_max

Value	Dose	Co-administered	Analyte	Population
1.9 μg/mL CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
8.24 μg × h/mL CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
11.17 μg × h/mL CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
7.5 μg × h/mL CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1.7 h CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.62 h CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
2.5 h CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.1% CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.3% CLINICAL TRIAL doi:10.1007/bf00544587	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TOLFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	Other AEs: Tachycardia, Chest pain... Other AEs: Tachycardia (8.5%) Chest pain Muscle pain (4.3%) Dysuria (8.5%) Nervous system disorder (8.5%) Nausea (4.3%) Vomiting (4.3%) Allergy (2.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/

AEs

AE	Significance	Dose	Population
Chest pain		200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Allergy	2.1%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Muscle pain	4.3%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Nausea	4.3%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Vomiting	4.3%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Dysuria	8.5%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Nervous system disorder	8.5%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/
Tachycardia	8.5%	200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9563211/

PubMed

Title	Date	PubMed
Tolfenamic acid downregulates BACE1 and protects against lead-induced upregulation of Alzheimer's disease related biomarkers.	2014-04	24462621
Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers.	2013-02-25	23165153
Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol.	2011-05-30	21187079
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Postoperative analgesic efficacy of meloxicam compared to tolfenamic acid in cats undergoing orthopaedic surgery.	2010-10	20840298
Effect of preventive (beta blocker) treatment, behavioural migraine management, or their combination on outcomes of optimised acute treatment in frequent migraine: randomised controlled trial.	2010-09-29	20880898
Activating transcription factor 2 (ATF2) controls tolfenamic acid-induced ATF3 expression via MAP kinase pathways.	2010-09-16	20581861
Occurrence and risk assessment of acidic pharmaceuticals in the Yellow River, Hai River and Liao River of north China.	2010-07-15	20493517
Apoptotic Effect of Tolfenamic Acid in KB Human Oral Cancer Cells: Possible Involvement of the p38 MAPK Pathway.	2010-07	20664734
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.	2010-07	20544456
Novel milk-based oral formulations: proof of concept.	2010-05-10	20117197
Pharmacokinetic and pharmacodynamic modelling of marbofloxacin administered alone and in combination with tolfenamic acid in goats.	2010-05	19299172
Confirmatory analysis of non-steroidal anti-inflammatory drugs in bovine milk by high-performance liquid chromatography with fluorescence detection.	2010-04-23	20227702
Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori.	2010-03-21	20200713
Combined treatment of pancreatic cancer with mithramycin A and tolfenamic acid promotes Sp1 degradation and synergistic antitumor activity.	2010-02-01	20086170
Regulation of HIV-1 transcription in cells of the monocyte-macrophage lineage.	2009-12-23	20030845
Thermodynamic and structural study of tolfenamic acid polymorphs.	2009-12-05	19632801
Development of a rapid, multi-class method for the confirmatory analysis of anti-inflammatory drugs in bovine milk using liquid chromatography tandem mass spectrometry.	2009-11-13	19467664
Eicosanoids influence insect susceptibility to nucleopolyhedroviruses.	2009-11	19761772
Tolfenamic acid inhibits esophageal cancer through repression of specificity proteins and c-Met.	2009-07	19406933
Anti-inflammatory, antiproliferative, and radical-scavenging activities of tolfenamic acid and its metal complexes.	2009-06	19551737
The nonsteroidal anti-inflammatory drug tolfenamic acid inhibits BT474 and SKBR3 breast cancer cell and tumor growth by repressing erbB2 expression.	2009-05	19435870
The relationship between diphenylamine structure and NSAIDs-induced hepatocytes injury.	2009-04-25	19429231
Polymer-induced heteronucleation of tolfenamic acid: structural investigation of a pentamorph.	2009-04-08	19334766
Thermodynamics of lipophilic drug binding to intestinal fatty acid binding protein and permeation across membranes.	2009-03-07	19265444
Tolfenamic acid enhances pancreatic cancer cell and tumor response to radiation therapy by inhibiting survivin protein expression.	2009-03	19258429
Investigating AP-2 and YY1 protein expression as a cause of high HER2 gene transcription in breast cancers with discordant HER2 gene amplification.	2009	20025767
Current migraine management - patient acceptability and future approaches.	2008-12	19337450
ESE-1/EGR-1 pathway plays a role in tolfenamic acid-induced apoptosis in colorectal cancer cells.	2008-12	19074849
Efficacy of tolfenamic acid and meloxicam in the control of postoperative pain following ovariohysterectomy in the cat.	2008-11	18565201
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.	2008-10	19209286
Assessment of the duration of the pain response associated with lameness in dairy cows, and the influence of treatment.	2008-10	18836500
Poloxamer 407 as a solubilising agent for tolfenamic acid and as a base for a gel formulation.	2008-09-02	18598763
In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions.	2008-08	18816299
Effects of meloxicam or tolfenamic acid administration on the pain and stress responses of Merino lambs to mulesing.	2008-08	18673471
Effects of fenamate on inhibitory postsynaptic currents in Purkinje's cells.	2008-05	19145282
catena-Poly[[bis-[2-(2,3-dimethyl-anilino)benzoato-κO]cadmium(II)]-di-μ-3-pyridylmethanol-κN:O;κO:N].	2008-02-06	21201841
The effect of suspended particles coated by humic acid on the toxicity of pharmaceuticals, estrogens, and phenolic compounds.	2008-02	17765969
Confirmatory identification of sixteen non-steroidal anti-inflammatory drug residues in raw milk by liquid chromatography coupled with ion trap mass spectrometry.	2008	18278821
Field evaluation of the efficacy of tolfenamic acid administered in one single preoperative injection for the prevention of postoperative pain in the dog.	2007-12	17991217
Tolfenamic acid is a potent CYP1A2 inhibitor in vitro but does not interact in vivo: correction for protein binding is needed for data interpretation.	2007-09	17618427
Inhibition of human thiopurine S-methyltransferase by various nonsteroidal anti-inflammatory drugs in vitro: a mechanism for possible drug interactions.	2007-09	17553913
Nonsteroidal anti-inflammatory drugs in cats: a review.	2007-07	17451496
Acute migraine: Current treatment and emerging therapies.	2007-06	18488069
Eicosanoid biosynthesis inhibitors increase the susceptibility of Lymantria dispar to nucleopolyhedrovirus LdMNPV.	2007-06	17386933
Regulation of vascular endothelial growth factor receptor-1 expression by specificity proteins 1, 3, and 4 in pancreatic cancer cells.	2007-04-01	17409437
Rapid method for the determination of non-steroidal anti-inflammatory drugs in animal tissue by liquid chromatography-mass spectrometry with ion-trap detector.	2007-03-14	17386745
Characterization and physical stability of tolfenamic acid-PVP K30 solid dispersions.	2007	17484143
The use of combination therapies in the acute management of migraine.	2006-09	19412476
Human pharmacokinetics of tolfenamic acid, a new anti-inflammatory agent.	1981	7238564

Patents

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).

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:54:10 GMT 2025` Edited by `admin` on `Wed Apr 02 06:54:10 GMT 2025`
Record UNII	3G943U18KM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-757873

Preferred Name

English

TOLFENAMIC ACID

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

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