Tiaprofenic acid

Tiaprofenic acid
Tiaprofenic acid
Systematic (IUPAC) name
(RS)-2-(5-benzoyl-2-thienyl)propanoic acid
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. C
Legal status POM
Routes oral
Pharmacokinetic data
Bioavailability 90%
Metabolism 10% hepatic
Half-life 1.5-2.5h
Excretion 50-80% urine
Identifiers
CAS number 33005-95-7 YesY
ATC code M01AE11
PubChem CID 5468
DrugBank DB01600
ChemSpider 5269 YesY
UNII 1LS1T6R34C YesY
KEGG D01325 YesY
ChEBI CHEBI:32221 N
ChEMBL CHEMBL365795 YesY
Synonyms 5-Benzoyl-α-methyl-2-thiopheneacetic acid
Chemical data
Formula C14H12O3S 
Mol. mass 260.309
SMILES eMolecules & PubChem
 N(what is this?)  acid (verify)

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.[1] It is contraindicated in patients with cystitis and urinary tract infections.

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

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. 

External links

v · d · eNon-steroidal anti-inflammatory drug (NSAID) products (primarily M01A and M02A, also N02BA)
Salicylates
Arylalkanoic acids
2-Arylpropionic acids
(profens)
Ibuprofen • Alminoprofen • Benoxaprofen • Carprofen • Dexibuprofen • Dexketoprofen • Fenbufen • Fenoprofen • Flunoxaprofen • Flurbiprofen • Ibuproxam • Indoprofen† • Ketoprofen • Ketorolac • Loxoprofen • Miroprofen • Naproxen • Oxaprozin • Pirprofen • Suprofen • Tarenflurbil • Tiaprofenic acid
N-Arylanthranilic acids
(fenamic acids)
Pyrazolidine derivatives
Oxicams
COX-2 inhibitors
Celecoxib • Deracoxib‡ • Etoricoxib • Firocoxib‡ • Lumiracoxib† • Parecoxib • Rofecoxib† • Valdecoxib†
Sulfonanilides
Topically used products
COX-inhibiting nitric oxide donators
Others
Items listed in bold indicate initially developed compounds of specific groups. †Withdrawn drugs. ‡Veterinary use medications.
v · d · eAnti-inflammatory products (M01A)
Pyrazolidine/Butylpyrazolidines
Acetic acid derivatives
and related substances
Oxicams
Propionic acid derivatives
Alminoprofen • Benoxaprofen • Dexibuprofen • Dexketoprofen • Fenbufen • Fenoprofen • Flunoxaprofen • Flurbiprofen • Ibuprofen • Ibuproxam • Indoprofen • Ketoprofen • Naproxen • Oxaprozin • Pirprofen • Suprofen • Tiaprofenic acid
Fenamates
Coxibs
Other

M: MUS, DF+DRCT

anat (h/n, u, t/d, a/p, l)/phys/devp/hist

noco(m, s, c)/cong(d)/tumr, sysi/epon, injr

proc, drug (M1A/3)


Stub icon This drug article relating to the musculoskeletal system is a stub. You can help Wikipedia by expanding it.