Tiaprofenic acid

Tiaprofenic acid

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	C
Routes of administration	oral
ATC code	M01AE11 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	90%
Metabolism	10% hepatic
Biological half-life	1.5-2.5h
Excretion	50-80% urine
Identifiers
IUPAC name (RS)-2-(5-benzoyl-2-thienyl)propanoic acid
Synonyms	5-Benzoyl-α-methyl-2-thiopheneacetic acid
CAS Number	33005-95-7 Y
PubChem CID	5468
DrugBank	DB01600 Y
ChemSpider	5269 Y
UNII	1LS1T6R34C
KEGG	D01325 Y
ChEBI	CHEBI:32221 Y
ChEMBL	CHEMBL365795 Y
ECHA InfoCard	100.046.649
Chemical and physical data
Formula	C14H12O3S
Molar mass	260.309
3D model (Jmol)	Interactive image
Chirality	Racemic 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

Tiaprofenic acid is a non-steroidal 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.

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.

Long-term use of tiaprofenic acid is associated with severe cystitis, roughly 100 times more commonly than other NSAIDs. It is contraindicated in patients with cystitis and urinary tract infections.

The earliest reports of clinical use are from France in 1975

It is marketed under the trade names Surgam, Surgamyl and Tiaprofen, and in generic formulations. A sustained-release preparation is available. It is an isomer of Suprofen.