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HomeProduct name listTiaprofenic acid

Tiaprofenic acid

Synonym(s):(±)-Tiaprofenic acid

  • CAS NO.:33005-95-7
  • Empirical Formula: C14H12O3S
  • Molecular Weight: 260.31
  • MDL number: MFCD00866089
  • EINECS: 251-329-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-08 20:21:46
Tiaprofenic acid Structural

What is Tiaprofenic acid?

Absorption

Bioavailability is 90% following oral administration.

Chemical properties

White or almost white, crystalline powder.

Originator

Surgam,Roussel,France,1975

The Uses of Tiaprofenic acid

Antiinflammatory;Cyclooxygenase inhibitor

Indications

Tiaprofenic acid is used to treat pain, especially arthritic pain.

Background

Tiaprofenic acid is a non-steroidal anti-inflammatory drug employed in the treatment of pain, particularly arthritis pain. It belongs to the arylpropionic acid (profen) group of nonsteroidal anti-inflammatory drugs (NSAIDs).

What are the applications of Application

Tiaprofenic Acid is a non-steroidal anti-inflammatory compound on in vitro cells

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

Pharmacokinetics

Tiaprofenic acid is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain. The typical adult dose is 300mg twice daily. This drug is not recommended for use in the pediatric population.

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

Hepatic (10%). Sparingly metabolised in the liver to two inactive metabolites.

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.

Properties of Tiaprofenic acid

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.
form  neat
pka 4.05±0.10(Predicted)
form  Solid
color  White to Almost white
λmax 314nm(Phosphate buffer sol.)(lit.)
Merck  14,9422

Safety information for Tiaprofenic acid

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H301:Acute toxicity,oral
H361:Reproductive toxicity
Precautionary Statement Codes P201:Obtain special instructions before use.

Computed Descriptors for Tiaprofenic acid

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