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Merck

T0535

Tolfenamic acid

NSAID

Synonym(s):

2 (3-Chloro-2-methylanilino)benzoic acid, 2-([3-Chloro-2-methylphenyl]amino)benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C14H12ClNO2
CAS Number:
13710-19-5
Molecular Weight:
261.70
NACRES:
NA.77
PubChem Substance ID:
24899896
UNSPSC Code:
12352202
EC Number:
237-264-3
MDL number:
MFCD00133865

Product Name

Tolfenamic acid, NSAID

InChI key

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)

SMILES string

Cc1c(Cl)cccc1Nc2ccccc2C(O)=O

assay

≥98% (TLC)

form

powder

solubility

ethanol: 50 mg/mL, clear, greenish-yellow

Quality Level

200

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Application

Tolfenamic acid has been used in Arabidopsis bud assay for activity comparison with quinazolinedione derivatives (QADD) based compounds.

Biochem/physiol Actions

Non-steroidal anti-inflammatory agent. Interferes with synthesis of β-amyloid precursor protein, and thus Aβ peptides, by promoting degradation of an essential transcription factor.
Tolfenamic acid is involved in the inhibition of prostaglandin synthesis. It also plays a role in apoptosis of head and neck cancer cells.

General description

Tolfenamic acid is a fenamate and is made up of a monocarboxylate diphenylamine nucleus.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000451944
0000451944
SLCN8296
SLBP6503V
SLBF8628V

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R A Tokola et al.
Cephalalgia : an international journal of headache, 4(4), 253-263 (1984-12-01)
Tolfenamic acid is a fenamate which inhibits prostaglandin (PG) biosynthesis and may act as a PG antagonist as well. Caffeine and metoclopramide are used in combination with analgesics and ergotamine in the treatment of migraine attacks, but controlled clinical studies
Polymer-induced heteronucleation of tolfenamic acid: structural investigation of a pentamorph
Lopez M V, et al.
Journal of the American Chemical Society, 131(13), 4554-4555 (2009)
Cyril Hamiaux et al.
The Biochemical journal, 476(12), 1843-1856 (2019-06-13)
Strigolactones (SLs) are multifunctional plant hormones regulating essential physiological processes affecting growth and development. In vascular plants, SLs are recognized by α/β hydrolase-fold proteins from the D14/DAD2 (Dwarf14/Decreased Apical Dominance 2) family in the initial step of the signaling pathway.
Chemical synthesis and characterization of a new quinazolinedione competitive antagonist for strigolactone receptors with an unexpected binding mode
Hamiaux C, et al.
The Biochemical Journal, 476(12), 1843-1856 (2019)
Vilmalí López-Mejías et al.
Journal of the American Chemical Society, 131(13), 4554-4555 (2009-04-02)
The nonsteroidal anti-inflammatory drug (NSAID) tolfenamic acid (TA), previously thought to be dimorphic, is demonstrated to have at least five polymorphs. The new forms were uncovered through the emerging screening technique of polymer-induced heteronucleation (PIHn). The presence of conformational changes
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