Tiaprofenic acid

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 in 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
IUPAC name
  • (RS)-2-(5-benzoyl-2-thienyl)propanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.649
Chemical and physical data
FormulaC14H12O3S
Molar mass260.31 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C(c1sc(cc1)C(C(=O)O)C)c2ccccc2
InChI
  • 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) Y
  • Key:GUHPRPJDBZHYCJ-UHFFFAOYSA-N Y
  (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 it should be used with caution 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
  1. Crawford MLA, 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, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.
  • Manufacturer Data Sheet


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