Tiaprofenic acid Chemical Properties

Melting point:

96° (isopropyl ether)

Boiling point:

373.57°C (rough estimate)

Density 

1.2959 (rough estimate)

refractive index 

1.5050 (estimate)

storage temp. 

2-8°C(protect from light)

solubility 

Practically insoluble in water, freely soluble in acetone, in ethanol (96 per cent) and in methylene chloride.

pka

4.05±0.10(Predicted)

color 

White to Almost white

λmax

314nm(Phosphate buffer sol.)(lit.)

Merck 

14,9422

Safety Information

RIDADR 

UN 2811 6.1/PG III

RTECS 

XM7580000

HS Code 

2934.99.3000

HazardClass 

6.1

PackingGroup 

III

Tiaprofenic acid Usage And Synthesis

Chemical Properties

White or almost white, crystalline powder.

Originator

Surgam,Roussel,France,1975

Uses

Antiinflammatory;Cyclooxygenase inhibitor

Definition

ChEBI: An aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group.

Manufacturing Process

A mixture of 10.3 g of thiophene-2α-methylacetic acid [prepared by process of Bercot-Vatteroni, et al., Bull. Soc. Chim. (1961) pp. 1820-21], 11.10 g of benzoyl chloride and a suspension of 23.73 g of aluminum chloride in 110 cc of chloroform was allowed to stand for 15 minutes and was then poured into a mixture of ice and hydrochloric acid. The chloroform phase was extracted with a 10% aqueous potassium carbonate solution and the aqueous alkaline phase was acidified with N hydrochloric acid and was then extracted with ether. The ether was evaporated off and the residue was crystallized from carbon tetrachloride to obtain a 54% yield of 5-benzoyl-thiophene-2α-methylacetic acid melting at 83°C to 85°C. The product occurred in the form of colorless crystals soluble in dilute alkaline solutions, alcohol and ether and insoluble in water.

Therapeutic Function

Antiinflammatory

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 - avoid long term use with edoxaban.
Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin concentration.
Antivirals: increased risk of haematological toxicity with zidovudine; concentration 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

Sparingly metabolised in the liver to two inactive metabolites. Excretion of tiaprofenic acid and its metabolites are mainly in the urine in the form of acyl glucuronides; some is excreted in the bile.

Tiaprofenic acid(33005-95-7)Related Product Information

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