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Key Documents

T0535

Sigma-Aldrich

Tolfenamic acid

NSAID

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C14H12ClNO2
Numéro CAS:
Poids moléculaire :
261.70
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352202
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Pureté

≥98% (TLC)

Forme

powder

Solubilité

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

Chaîne SMILES 

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)

Clé InChI

YEZNLOUZAIOMLT-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Conseils de prudence

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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.
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)

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