Tolfenamic acid Chemical Properties

Melting point:

210-214°C

Boiling point:

405.4±40.0 °C(Predicted)

Density 

1.2037 (rough estimate)

refractive index 

1.5270 (estimate)

storage temp. 

2-8°C

solubility 

Practically insoluble in water, soluble in dimethylformamide, sparingly soluble in ethanol and in methylene chloride. It dissolves in dilute solutions of alkali hydroxides.

pka

3.66±0.36(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

Soluble in water (slightly), acetone (~10 mg/ml), DMSO (52 mg/ml at 25°C), methanol (~10 mg/ml) and ethanol (50 mg/ml).

Merck 

14,9513

InChIKey

YEZNLOUZAIOMLT-UHFFFAOYSA-N

CAS DataBase Reference

13710-19-5(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 2-[(3-chloro-2-methylphenyl)amino]- (13710-19-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

CB2687500

HazardClass 

6.1

PackingGroup 

III

HS Code 

29224919

MSDS

• Language:English Provider:N-(3-Chloro-ortho-tolyl) anthranilic acid
• Language:English Provider:SigmaAldrich

Tolfenamic acid Usage And Synthesis

Chemical Properties

White Solid

Uses

antiinflammatory, analgesia

Uses

Amidated GRF fragment equipotent to GRF in release of somatotropin from anterior pituitary

Uses

A non steroidal anti-inflammatory agent found to inhibit COX-2 isoenzymes

Uses

Tolfenamic acid is a non-steroidal anti-inflammatory agent. It interferes with synthesis of β-amyloid precursor protein, and thus Aβ peptides, by promoting degradation of an essential transcription factor. It inhibits fMLP- and A23187-induced Ca2+ influx in human PMNL with an IC50 value of approximately 20 μM.

Uses

Non-steroidal anti-inflammatory drugs (NSAIDs).

Definition

ChEBI: An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 3-chloro-2-methylphenyl group. Tolfenamic acid is used specifically for relieving the pain of migraine. It also shows anticancer activity.

General Description

Tolfenamic Acid is an anthranilic acid derivative and a non-steroidal anti-inflammatory drug (NSAID). Its applications in treating pancreatic, esophageal, colorectal and lung cancer is being investigated.

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.

Clinical Use

NSAID:
Treatment of migraine

Synthesis

Tolfenamic acid is obtained by condensation of 2-chlorobenzoic acid with 3- chloro-2-methyl-phenylamine using CuBr2 in diethylenglycol dimethyl ether .

Veterinary Drugs and Treatments

Tolfenamic acid may be useful for the treatment of acute or chronic pain and/or inflammation in dogs and acute pain/inflammation in cats. In Europe, it is also approved for use in cattle.

Drug interactions

Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia.
Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage).
Antibacterials: possibly increased risk of convulsions with quinolones.
Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban.
Antidepressants: increased risk of bleeding with SSRIs and venlafaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin concentration.
Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir.
Ciclosporin: may potentiate nephrotoxicity.
Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib.
Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics.
Lithium: excretion decreased.
Pentoxifylline: increased risk of bleeding.
Tacrolimus: increased risk of nephrotoxicity

Metabolism

Tolfenamic acid is metabolised in the liver; the metabolites and unchanged drug are conjugated with glucuronic acid. About 90
% of an ingested dose is excreted in the urine and the remainder in the faeces.

Tolfenamic acid(13710-19-5)Related Product Information

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