Tolfenamic acid Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

Tolfenamic acid Chemical Properties,Usage,Production

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.