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T0535

Sigma-Aldrich

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
EC Number:
237-264-3
MDL number:
MFCD00133865
UNSPSC Code:
12352202
PubChem Substance ID:
24899896
NACRES:
NA.77

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

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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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Tolfenamic acid, metoclopramide, caffeine and their combinations in the treatment of migraine attacks
Tokola R A, et al.
Cephalalgia, 4(4), 253-263 (1984)
Umesh T Sankpal et al.
The Prostate, 72(15), 1648-1658 (2012-04-05)
Specificity protein (Sp) transcription factors are implicated in critical cellular and molecular processes associated with cancer that impact tumor growth and metastasis. The non-steroidal anti-inflammatory drug, tolfenamic acid (TA) is known to inhibit Sp proteins in some human cancer cells
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