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Tiaprofenic acid

From Wikipedia, the free encyclopedia
NSAID analgesic drug
Pharmaceutical compound
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
Pharmacokinetic data
Bioavailability90%
Metabolism10% liver
Eliminationhalf-life1.5-2.5h
Excretion50-80% urine
Identifiers
  • (RS)-2-(5-benzoyl-2-thienyl)propanoic acid
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.046.649Edit this at Wikidata
Chemical and physical data
FormulaC14H12O3S
Molar mass260.31 g·mol−1
3D model (JSmol)
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)

Tiaprofenic acid is anonsteroidal anti-inflammatory drug (NSAID) of thearylpropionic acid (profen) class, used to treat pain, especiallyarthritic pain. The typical adult dose is 300 mg twice daily. It is not recommended for children.

Long-term use of tiaprofenic acid is associated with severecystitis, 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 theliver to two inactive metabolites. Most of the drug is eliminated unchanged in theurine. 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 ingeneric formulations. A sustained-release preparation is available. It is anisomer ofSuprofen.

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]
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others


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