Tiaprofenic acid

Tiaprofenic acid
Clinical data
Trade names	Surgam, Surgamyl, Tiaprofen, others
Other names	5-Benzoyl-α-methyl-2-thiopheneacetic acid
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	C;
Routes of; administration	By mouth
ATC code	M01AE11 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	90%
Metabolism	10% liver
Elimination half-life	1.5-2.5h
Excretion	50-80% urine
Identifiers
	IUPAC name (RS)-2-(5-benzoyl-2-thienyl)propanoic acid;
CAS Number	33005-95-7 ;
PubChem CID	5468;
DrugBank	DB01600 ;
ChemSpider	5269 ;
UNII	1LS1T6R34C;
KEGG	D01325 ;
ChEBI	CHEBI:32221 ;
ChEMBL	ChEMBL365795 ;
CompTox Dashboard (EPA)	DTXSID5023665 ;
ECHA InfoCard	100.046.649
Chemical and physical data
Formula	C14H12O3S
Molar mass	260.31 g·mol−1
3D model (JSmol)	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) ; Key:GUHPRPJDBZHYCJ-UHFFFAOYSA-N ;
	(verify)

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.

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

^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.

External links

Manufacturer Data Sheet [1]

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[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.

[Fis2006-2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.

[1]

[2]

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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