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:
Molecular Weight:
261.70
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
237-264-3
MDL number:
Quality Level
assay
≥98% (TLC)
form
powder
solubility
ethanol: 50 mg/mL, clear, greenish-yellow
SMILES string
Cc1c(Cl)cccc1Nc2ccccc2C(O)=O
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
General description
Tolfenamic acid is a fenamate and is made up of a monocarboxylate diphenylamine nucleus.
Application
Tolfenamic acid has been used in Arabidopsis bud assay for activity comparison with quinazolinedione derivatives (QADD) based compounds.
Biochem/physiol Actions
Tolfenamic acid is involved in the inhibition of prostaglandin synthesis. It also plays a role in apoptosis of head and neck cancer cells.
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.
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signalword
Danger
hcodes
pcodes
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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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
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
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)