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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)

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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
Don Eslin et al.
Molecular carcinogenesis, 52(5), 377-386 (2012-01-04)
Current therapeutic options for recurrent neuroblastoma have poor outcomes that warrant the development of novel therapeutic strategies. Specificity protein (Sp) transcription factors regulate several genes involved in cell proliferation, survival, and angiogenesis. Sp1 regulates genes believed to be important determinants
Sung Un Kang et al.
PloS one, 7(4), e34988-e34988 (2012-04-27)
Nonsteroidal anti-inflammatory drug-activated gene-1 (NAG-1) is induced by nonsteroidal anti-inflammatory drugs and possesses proapoptotic and antitumorigenic activities. Although tolfenamic acid (TA) induces apoptosis in head and neck cancer cells, the relationship between NAG-1 and TA has not been determined. This
Alketa Tarushi et al.
Dalton transactions (Cambridge, England : 2003), 41(23), 7082-7091 (2012-05-05)
The interaction of Zn(II) with the non-steroidal anti-inflammatory drug tolfenamic acid leads to the formation of the structurally characterized trinuclear [Zn(3)(tolfenamato)(6)(CH(3)OH)(2)] complex. In the presence of the N,N'-donor heterocyclic ligands 1,10-phenanthroline and 2,2'-bipyridine at a range of ratios, the mononuclear
Alessandra Mattei et al.
Pharmaceutical research, 29(2), 460-470 (2011-09-01)
Crystallization from solution involves nucleation and growth; growth conditions greatly influence self-association behaviors of solute molecules in these steps, affecting crystal packing of organic molecules. We examined the role of pre-nucleation association to provide insights into the mutual influence between
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