Tiaprofenic acid

Summary

Tiaprofenic acid is a nonsteroidal anti-inflammatory drug (NSAID) of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain. The typical adult dose is 300 mg twice daily. It is not recommended for children.

Tiaprofenic acid
Clinical data
Trade namesSurgam, Surgamyl, Tiaprofen, others
Other names5-Benzoyl-α-methyl-2-thiopheneacetic acid
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • C
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability90%
Metabolism10% liver
Elimination half-life1.5-2.5h
Excretion50-80% urine
Identifiers
  • (RS)-2-(5-benzoyl-2-thienyl)propanoic acid
CAS Number
  • 33005-95-7 checkY
PubChem CID
  • 5468
DrugBank
  • DB01600 checkY
ChemSpider
  • 5269 checkY
UNII
  • 1LS1T6R34C
KEGG
  • D01325 checkY
ChEBI
  • CHEBI:32221 checkY
ChEMBL
  • ChEMBL365795 checkY
CompTox Dashboard (EPA)
  • DTXSID5023665 Edit this at Wikidata
ECHA InfoCard100.046.649 Edit this at Wikidata
Chemical and physical data
FormulaC14H12O3S
Molar mass260.31 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
  • O=C(c1sc(cc1)C(C(=O)O)C)c2ccccc2
  • InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17) checkY
  • Key:GUHPRPJDBZHYCJ-UHFFFAOYSA-N checkY
  (verify)

Long-term use of tiaprofenic acid is associated with severe cystitis, roughly 100 times more commonly than other NSAIDs.[1] It is contraindicated in patients with cystitis and urinary tract infections. It is sparingly metabolised in the liver to two inactive metabolites. Most of the drug is eliminated unchanged in the urine. Renal disease impairs excretion, and should be used cautiously in renal disease.

It was patented in 1969 and approved for medical use in 1981.[2] It is available in generic formulations. A sustained-release preparation is available. It is an isomer of Suprofen.

References edit

  1. ^ Crawford ML, Waller PC, Wood SM (1997). "Severe cystitis associated with tiaprofenic acid". British Journal of Urology. 79 (4): 578–584. doi:10.1046/j.1464-410X.1997.00094.x. PMID 9126086.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.

External links edit

  • Manufacturer Data Sheet [1]