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{{Drugbox|
{{Drugbox
|IUPAC_name = 5-Benzoyl-α-methyl-2-thiopheneacetic acid  
| verifiedrevid = 470610046
| IUPAC_name = (''RS'')-2-(5-benzoyl-2-thienyl)propanoic acid
| image = Tiaprofenic acid.svg
| image = Tiaprofenic acid.svg
| CAS_number= 33005-95-7
| width = 200
| ATC_prefix=M01
| imagename = 1 : 1 mixture (racemate)
| ATC_suffix=AE11
| drug_name = Tiaprofenic acid
| ATC_supplemental=
 
| PubChem=5468
<!--Clinical data-->
| DrugBank=
| tradename =
| C=14 | H=12 | O=3 | S=1
| Drugs.com = {{drugs.com|CONS|tiaprofenic_acid}}
| molecular_weight = 260.309
| bioavailability= 90%
| metabolism = 10% hepatic
| elimination_half-life=1.5-2.5h
| excretion = 50-80% urine
| pregnancy_category = C
| pregnancy_category = C
| legal_status = POM
| legal_status = POM
| routes_of_administration= oral
| routes_of_administration = oral
 
<!--Pharmacokinetic data-->
| bioavailability = 90%
| metabolism = 10% hepatic
| elimination_half-life = 1.5-2.5h
| excretion = 50-80% urine
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 33005-95-7
| ATC_prefix = M01
| ATC_suffix = AE11
| PubChem = 5468
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01600
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5269
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1LS1T6R34C
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01325
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 32221
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 365795
 
<!--Chemical data-->
| C=14 | H=12 | O=3 | S=1
| molecular_weight = 260.309
| smiles = O=C(c1sc(cc1)C(C(=O)O)C)c2ccccc2
| InChI = 1/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)
| InChIKey = GUHPRPJDBZHYCJ-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GUHPRPJDBZHYCJ-UHFFFAOYSA-N
| synonyms = <small>5-Benzoyl-α-methyl-2-thiopheneacetic acid</small>
}}
}}


'''Tiaprofenic acid''' is a [[non-steroidal anti-inflammatory drug]] of the arylpropionic acid (profen) class, used to treat pain, especially [[Arthritis|arthritic]] pain. The typical adult dose is 300mg twice daily. It is not recommended in children.
'''Tiaprofenic acid''' is a [[non-steroidal anti-inflammatory drug]] (NSAID) of the arylpropionic acid (profen) class, used to treat pain, especially [[Arthritis|arthritic]] pain. The typical adult dose is 300&nbsp;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.
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.


Longterm 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.
Long-term use of tiaprofenic acid is associated with severe [[cystitis]], roughly 100 times more commonly than other NSAIDs.<ref>{{cite journal | author = Crawford MLA, Waller PC, Wood SM | title = Severe cystitis associated with tiaprofenic acid | journal = British Journal of Urology | year = 1997 | volume = 79 | issue = 4 | pages = 578–584 | doi = 10.1046/j.1464-410X.1997.00094.x | pmid = 9126086}}</ref> 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 drug|generic]] formulations. A sustained-release preparation is available.
The earliest reports of clinical use are from France in 1975 <ref>{{cite journal | author = Pons J,  Pasturel A | title =  [How to improve postoperative complications in stomatological, maxillofacial and plastic surgery: evaluation of tiaprofenic acid]. [French] | journal = Revue d Odonto-Stomatologie.  | year = 1975 | volume = 4 | issue = 6 pages = 535-7}}</ref>
 
It is marketed under the trade names '''Surgam''', '''Surgamyl''' and '''Tiaprofen''', and in [[Generic drug|generic]] formulations. A sustained-release preparation is available. It is [[isomer]] with [[Suprofen]].


== References ==
== References ==
 
{{reflist}}
* Crawford MLA, Waller PC, Wood SM. Severe cystitis associated with tiaprofenic acid. ''British Journal of Urology'' 1997; 79(4): 578-584.


== External links ==
== External links ==
* Manufacturer Data Sheet [http://www.medsafe.govt.nz/profs/Datasheet/s/Surgamtab.htm]
* Manufacturer Data Sheet [http://www.medsafe.govt.nz/profs/Datasheet/s/Surgamtab.htm]{{dead link|date=November 2011}}


{{NSAIDs}}
{{Anti-inflammatory and antirheumatic products}}
{{Anti-inflammatory and antirheumatic products}}
{{pharma-stub}}


[[de:Tiaprofensäure]]
{{DEFAULTSORT:Tiaprofenic Acid}}
[[Category:Non-steroidal anti-inflammatory drugs]]
[[Category:Aromatic ketones]]
[[Category:Thiophenes]]
 


[[Category:Non-steroidal anti-inflammatory drugs]]
{{musculoskeletal-drug-stub}}
[[Category:Drugs]]
{{WikiDoc Sources}}

Revision as of 14:57, 13 April 2015

Tiaprofenic acid
File:Tiaprofenic acid.svg
Clinical data
Synonyms5-Benzoyl-α-methyl-2-thiopheneacetic acid
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • C
Routes of
administration		oral
ATC code
Legal status
Legal status
  • POM
Pharmacokinetic data
Bioavailability90%
Metabolism10% hepatic
Elimination half-life1.5-2.5h
Excretion50-80% urine
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC14H12O3S
Molar mass260.309
3D model (JSmol)
  (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.

The earliest reports of clinical use are from France in 1975 [2]

It is marketed under the trade names Surgam, Surgamyl and Tiaprofen, and in generic formulations. A sustained-release preparation is available. It is isomer with 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. ↑ Pons J, Pasturel A (1975). "[How to improve postoperative complications in stomatological, maxillofacial and plastic surgery: evaluation of tiaprofenic acid]. [French]". Revue d Odonto-Stomatologie. 4 (6 pages = 535-7).

External links


Template:Musculoskeletal-drug-stub

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