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Showing drug card for Tiaprofenic acid (DB01600)

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Version 2.5
Creation Date 2007-08-29 18:44:06
Update Date 2009-06-23 18:06:49
Primary Accession Number DB01600
Secondary Accession Number Not Available
Name Tiaprofenic acid
Drug Type
  • Approved
  • Small Molecule
Description Tiaprofenic acid is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain.
Synonyms
  1. 2-(5-Benzyl-2-thienyl)propionsaeure
  2. 5-Benzoyl-alpha-methyl-2-thiopheneacetic acid
  3. Acide tiaprofenique [inn-french]
  4. Acido tiaprofenico [inn-spanish]
  5. Acidum tiaprofenicum [inn-latin]
  6. Tiaprofensaeure
Brand Names
  1. Apo-Tiaprofenic Tablets
  2. Dom-tiaprofenic
  3. Novo-Tiaprofenic
  4. Nu-Tiaprofenic
  5. PMS-tiaprofenic
  6. Surgam
  7. Surgam SR
  8. Tiaprofenic-200 - Tab
  9. Tiaprofenic-300 - Tab
Brand Mixtures Not Available
Chemical IUPAC Name 2-[5-(benzoyl)thiophen-2-yl]propanoic acid
Chemical Formula C14H12O3S
Chemical Structure Structure
CAS Registry Number 33005-95-7
InChI Identifier 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)/f/h16H
InChI Key GUHPRPJDBZHYCJ-WYUMXYHSCF
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 5468 Link Image
PubChem Substance 10321760 Link Image
ChEBI ID Not Available
PharmGKB ID PA10212 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02136112 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Tiaprofenic_acid Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 260.3080
Monoisotopic Molecular Weight 260.0507
State Solid
Melting Point 96 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.24e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP 3.22 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.91 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@H](C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1
Canonical SMILES CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1
Drug Category
  • Anti-Inflammatory Agents, Non-Steroidal
ATC Codes Not Available
AHFS Codes Not Available
Indication Used to treat pain, especially arthritic pain.
Pharmacology Tiaprofenic acid is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain. The typical adult dose is 300mg twice daily. It is not recommended in children.
Mechanism of Action Tiaprofenic acid belongs to a group of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the production of a chemical (prostaglandin) which the body produces in response to injury or certain diseases. This prostaglandin would otherwise go on to cause swelling, pain and inflammation.
Absorption Bioavailability is 90% following oral administration.
Toxicity Not Available
Protein Binding Not Available
Biotransformation Hepatic (10%). Sparingly metabolised in the liver to two inactive metabolites.
Half Life 1.5-2.5 hours
Dosage Forms
Form Route
Capsule, extended release Oral
Tablet Oral
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions
Drug Interaction
Acenocoumarol Increased risk of bleeding.
Aminosalicylic Acid Increased risk of gastrointestinal bleeding.
Aspirin Increased risk of gastrointestinal bleeding.
Cholestyramine The bile acid sequestrant, Cholestyramine resin, may reduce Tiaprofenic acid absorption and therapeutic effect.
Citalopram Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Colesevelam The bile acid sequestrant, Colesevelam, may reduce Tiaprofenic acid absorption and therapeutic effect.
Colestipol The bile acid sequestrant, Colestipol, may reduce Tiaprofenic acid absorption and therapeutic effect.
Cyclosporine Tiaprofenic acid may increase the nephrotoxicity and/or the serum concentration of Cyclosporine. Consider altnerate therapy or monitor for increased Cyclosporine concentrations and nephrotoxicity during concomitant therapy.
Escitalopram Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Fluoxetine Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Fluvoxamine Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Ginkgo biloba Increaed risk of bleeding. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Ginseng Increaed risk of bleeding. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Ketorolac Concomitant therapy is contraindicated due to the risk of synergistic NSAID toxicity.
Lithium Tiaprofenic acid may increase the therapeutic/adverse effects of Lithium by increasing Lithium serum concentrations. Monitor for changes in the therapeutic/adverse effects of Lithium if Tiaprofenic acid is initiated, discontinued or dose changed.
Methotrexate Tiaprofenic acid may decrease Methotrexate excretion. Consider alternate therapy or monitor for Methotrexate toxicity.
Paroxetine Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Pemetrexed Tiaprofenic acid may decrease Pemetrexed excretion. Tiaprofenic acid should not be used around the time when Pemetrexed is administered.
Salsalate Increased risk of gastrointestinal bleeding.
Sertraline Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Warfarin Increased risk of bleeding.
Food Interactions
  • Avoid alcohol.
  • Take with food.
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Prostaglandin G/H synthase 2
Drug Target 1 [top]
Target 1 ID 290
Target 1 Name Prostaglandin G/H synthase 2
Target 1 Synonyms
  1. COX-2
  2. Cyclooxygenase- 2
  3. EC 1.14.99.1
  4. PGH synthase 2
  5. PGHS-2
  6. PHS II
  7. Prostaglandin G/H synthase 2 precursor
  8. Prostaglandin H2 synthase 2
  9. Prostaglandin-endoperoxide synthase 2
Target 1 Gene Name PTGS2
Target 1 Protein Sequence >Prostaglandin G/H synthase 2 precursor 
MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFYGENCSTPEFL
TRIKLFLKPTPNTVHYILTHFKGFWNVVNNIPFLRNAIMSYVLTSRSHLIDSPPTYNADY
GYKSWEAFSNLSYYTRALPPVPDDCPTPLGVKGKKQLPDSNEIVEKLLLRRKFIPDPQGS
NMMFAFFAQHFTHQFFKTDHKRGPAFTNGLGHGVDLNHIYGETLARQRKLRLFKDGKMKY
QIIDGEMYPPTVKDTQAEMIYPPQVPEHLRFAVGQEVFGLVPGLMMYATIWLREHNRVCD
VLKQEHPEWGDEQLFQTSRLILIGETIKIVIEDYVQHLSGYHFKLKFDPELLFNKQFQYQ
NRIAAEFNTLYHWHPLLPDTFQIHDQKYNYQQFIYNNSILLEHGITQFVESFTRQIAGRV
AGGRNVPPAVQKVSQASIDQSRQMKYQSFNEYRKRFMLKPYESFEELTGEKEMSAELEAL
YGDIDAVELYPALLVEKPRPDAIFGETMVEVGAPFSLKGLMGNVICSPAYWKPSTFGGEV
GFQIINTASIQSLICNNVKGCPFTSFSVPDPELIKTVTINASSSRSGLDDINPTVLLKER
STEL
Target 1 Number of Residues 614
Target 1 Molecular Weight 68997
Target 1 Theoretical pI 7.41
Target 1 GO Classification
Function
antioxidant activity
peroxidase activity
Process
Not Available
Component
Not Available
Target 1 General Function Involved in peroxidase activity
Target 1 Specific Function May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity
Target 1 Pathways
Name SMPDB Link KEGG Link
Prostaglandin and leukotriene metabolism map00590 Link Image
Target 1 Reactions
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-17
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 291988 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35354 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PGH2_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Microsome
  • microsomal membrane
  • peripheral membrane protein
Target 1 Gene Sequence >1815 bp 
ATGCTCGCCCGCGCCCTGCTGCTGTGCGCGGTCCTGGCGCTCAGCCATACAGCAAATCCT
TGCTGTTCCCACCCATGTCAAAACCGAGGTGTATGTATGAGTGTGGGATTTGACCAGTAT
AAGTGCGATTGTACCCGGACAGGATTCTATGGAGAAAACTGCTCAACACCGGAATTTTTG
ACAAGAATAAAATTATTTCTGAAACCCACTCCAAACACAGTGCACTACATACTTACCCAC
TTCAAGGGATTTTGGAACGTTGTGAATAACATTCCCTTCCTTCGAAATGCAATTATGAGT
TATGTGTTGACATCCAGATCACATTTGATTGACAGTCCACCAACTTACAATGCTGACTAT
GGCTACAAAAGCTGGGAAGCCTTCTCTAACCTCTCCTATTATACTAGAGCCCTTCCTCCT
GTGCCTGATGATTGCCCGACTCCCTTGGGTGTCAAAGGTAAAAAGCAGCTTCCTGATTCA
AATGAGATTGTGGAAAAATTGCTTCTAAGAAGAAAGTTCATCCCTGATCCCCAGGGCTCA
AACATGATGTTTGCATTCTTTGCCCAGCACTTCACGCATCAGTTTTTCAAGACAGATCAT
AAGCGAGGGCCAGCTTTCACCAACGGGCTGGGCCATGGGGTGGACTTAAATCATATTTAC
GGTGAAACTCTGGCTAGACAGCGTAAACTGCGCCTTTTCAAGGATGGAAAAATGAAATAT
CAGATAATTGATGGAGAGATGTATCCTCCCACAGTCAAAGATACTCAGGCAGAGATGATC
TACCCTCCTCAAGTCCCTGAGCATCTACGGTTTGCTGTGGGGCAGGAGGTCTTTGGTCTG
GTGCCTGGTCTGATGATGTATGCCACAATCTGGCTGCGGGAACACAACAGAGTATGCGAT
GTGCTTAAACAGGAGCATCCTGAATGGGGTGATGAGCAGTTGTTCCAGACAAGCAGGCTA
ATACTGATAGGAGAGACTATTAAGATTGTGATTGAAGATTATGTGCAACACTTGAGTGGC
TATCACTTCAAACTGAAATTTGACCCAGAACTACTTTTCAACAAACAATTCCAGTACCAA
AATCGTATTGCTGCTGAATTTAACACCCTCTATCACTGGCATCCCCTTCTGCCTGACACC
TTTCAAATTCATGACCAGAAATACAACTATCAACAGTTTATCTACAACAACTCTATATTG
CTGGAACATGGAATTACCCAGTTTGTTGAATCATTCACCAGGCAAATTGCTGGCAGGGTT
GCTGGTGGTAGGAATGTTCCACCCGCAGTACAGAAAGTATCACAGGCTTCCACTGACCAG
AGCAGGCAGATGAAATACCAGTCTTTTAATGAGTACCGCAAACGCTTTATGCTGAAGCCC
TATGAATCATTTGAAGAACTTACAGGAGAAAAGGAAATGTCTGCAGAGTTGGAAGCACTC
TATGGTGACATCGATGCTGTGGAGCTGTATCCTGCCCTTCTGGTAGAAAAGCCTCGGCCA
GATGCCATCTTTGGTGAAACCATGGTAGAAGTTGGAGCACCATTCTCCTTGAAAGGACTT
ATGGGTAATGTTATATGTTCTCCTGCCTACTGGAAGCCAAGCACTTTTGGTGGAGAAGTG
GGTTTTCAAATCATCAACACTGCCTCAATTCAGTCTCTCATCTGCAATAACGTGAAGGGC
TGTCCCTTTACTTCATTCAGTGTTCCAGATCCAGAGCTCATTAAAACAGTCACCATCAAT
GCAAGTTCTTCCCGCTCCGGACTAGATGATATCAATCCCACAGTACTACTAAAAGAACGT
TCGACTGAACTGTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID PTGS2 Link Image
Target 1 GenAtlas ID PTGS2 Link Image
Target 1 HGNC ID HGNC:9605 Link Image
Target 1 Chromosome Location 1
Target 1 Locus 1q25.2-q25.3
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Hla T, Neilson K: Human cyclooxygenase-2 cDNA. Proc Natl Acad Sci U S A. 1992 Aug 15;89(16):7384-8. [PubMed Link Image]
  2. Appleby SB, Ristimaki A, Neilson K, Narko K, Hla T: Structure of the human cyclo-oxygenase-2 gene. Biochem J. 1994 Sep 15;302 ( Pt 3):723-7. [PubMed Link Image]
  3. Kosaka T, Miyata A, Ihara H, Hara S, Sugimoto T, Takeda O, Takahashi E, Tanabe T: Characterization of the human gene (PTGS2) encoding prostaglandin-endoperoxide synthase 2. Eur J Biochem. 1994 May 1;221(3):889-97. [PubMed Link Image]
  4. Jones DA, Carlton DP, McIntyre TM, Zimmerman GA, Prescott SM: Molecular cloning of human prostaglandin endoperoxide synthase type II and demonstration of expression in response to cytokines. J Biol Chem. 1993 Apr 25;268(12):9049-54. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.