Chemical Properties
White or almost white, crystalline powder.
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.
Originator
Surgam,Roussel,France,1975
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.
