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Identification
NameTiaprofenic acid
Accession NumberDB01600
TypeSmall Molecule
GroupsApproved
Description

Tiaprofenic acid is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain.

Structure
Thumb
Synonyms
2-(5-Benzoyl-thiophen-2-yl)-propionic acid
2-(5-Benzyl-2-thienyl)propionsaeure
5-Benzoyl-alpha-methyl-2-thiopheneacetic acid
5-Benzoyl-alpha-methylthiophene-2-acetic acid
Acide tiaprofenique
Acido tiaprofenico
Acidum tiaprofenicum
alpha-Methyl-5-benzoyl-2-thienylacetic acid
Tiaprofensaeure
Tiaprofensäure
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Albert Tiafen SRcapsule (sustained-release)300 mgoralAventis Pharma IncNot applicableNot applicableCanada
Albert Tiafen Tab 200mgtablet200 mgoralAventis Pharma Inc1991-12-312004-07-30Canada
Albert Tiafen Tab 300mgtablet300 mgoralAventis Pharma Inc1991-12-312004-07-30Canada
Dom-tiaprofenictablet300 mgoralDominion Pharmacal2000-06-20Not applicableCanada
Dom-tiaprofenictablet200 mgoralDominion PharmacalNot applicableNot applicableCanada
Nu-tiaprofenic - Tab 200mgtablet200 mgoralNu Pharm Inc1995-12-312012-09-04Canada
Nu-tiaprofenic - Tab 300mgtablet300 mgoralNu Pharm Inc1995-12-312012-09-04Canada
Penta-tiaprofenic Tabletstablet300 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Penta-tiaprofenic Tabletstablet200 mgoralPentapharm Ltd.Not applicableNot applicableCanada
PMS-tiaprofenictablet300 mgoralPharmascience Inc1997-07-08Not applicableCanada
PMS-tiaprofenictablet200 mgoralPharmascience Inc1999-01-24Not applicableCanada
Surgamtablet300 mgoralSanofi Aventis Canada Inc1997-08-202007-11-22Canada
Surgam SRcapsule (sustained-release)300 mgoralSanofi Aventis Canada Inc1997-02-212007-07-31Canada
Surgam SR Cap 300mgcapsule (sustained-release)300 mgoralHoechst Roussel Canada Inc.1990-12-311999-08-11Canada
Surgam Tab 200mgtablet200 mgoralRoussel Canada Inc.1986-12-311997-08-05Canada
Surgam Tab 200mgtablet200 mgoralHoechst Roussel Canada Inc.1996-12-312001-07-20Canada
Surgam Tab 300mgtablet300 mgoralRoussel Canada Inc.1986-12-311997-08-05Canada
Surgam Tab 300mgtablet300 mgoralHoechst Roussel Canada Inc.1995-12-311999-08-11Canada
Surgam-SR Src 300mgcapsule (sustained-release)300 mgoralRoussel Canada Inc.1990-12-311996-09-09Canada
Teva-tiaprofenic Acidtablet200 mgoralTeva Canada Limited1996-12-31Not applicableCanada
Teva-tiaprofenic Acidtablet300 mgoralTeva Canada Limited1996-12-31Not applicableCanada
Tiaprofenic-200 - Tabtablet200 mgoralPro Doc Limitee1996-12-312009-07-23Canada
Tiaprofenic-300 - Tabtablet300 mgoralPro Doc Limitee1996-12-312009-07-23Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tiaprofenic Tablets -300mgtablet300 mgoralApotex Inc1994-12-31Not applicableCanada
Apo-tiaprofenic Tablets-200mgtablet200 mgoralApotex Inc1994-12-31Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
SurgamylNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1LS1T6R34C
CAS number33005-95-7
WeightAverage: 260.308
Monoisotopic: 260.05071494
Chemical FormulaC14H12O3S
InChI KeyInChIKey=GUHPRPJDBZHYCJ-UHFFFAOYSA-N
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)
IUPAC Name
2-(5-benzoylthiophen-2-yl)propanoic acid
SMILES
CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Acetophenone
  • Aryl ketone
  • Thiophene carboxylic acid or derivatives
  • Benzoyl
  • 2,5-disubstituted thiophene
  • Heteroaromatic compound
  • Thiophene
  • Ketone
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationTiaprofenic acid is used to treat pain, especially arthritic pain.
PharmacodynamicsTiaprofenic 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 actionTiaprofenic 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.
Related Articles
AbsorptionBioavailability is 90% following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic (10%). Sparingly metabolised in the liver to two inactive metabolites.

Route of eliminationNot Available
Half life1.5-2.5 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Tiaprofenic Acid Action PathwayDrug actionSMP00705
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9927
Blood Brain Barrier+0.9289
Caco-2 permeable+0.6039
P-glycoprotein substrateNon-substrate0.7298
P-glycoprotein inhibitor INon-inhibitor0.9534
P-glycoprotein inhibitor IINon-inhibitor0.9664
Renal organic cation transporterNon-inhibitor0.8998
CYP450 2C9 substrateNon-substrate0.6293
CYP450 2D6 substrateNon-substrate0.9226
CYP450 3A4 substrateNon-substrate0.8098
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8607
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.8958
CYP450 3A4 inhibitorNon-inhibitor0.9526
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.9398
CarcinogenicityNon-carcinogens0.7568
BiodegradationReady biodegradable0.7714
Rat acute toxicity3.1892 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9869
hERG inhibition (predictor II)Non-inhibitor0.9716
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral300 mg
Tabletoral200 mg
Capsule (sustained-release)oral300 mg
Prices
Unit descriptionCostUnit
Apo-Tiaprofenic 300 mg Tablet0.43USD tablet
Novo-Tiaprofenic 300 mg Tablet0.43USD tablet
Nu-Tiaprofenic 300 mg Tablet0.43USD tablet
Apo-Tiaprofenic 200 mg Tablet0.36USD tablet
Novo-Tiaprofenic 200 mg Tablet0.36USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point96 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0324 mg/mLALOGPS
logP3.22ALOGPS
logP3.66ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.19 m3·mol-1ChemAxon
Polarizability26.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesM01AE11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabTiaprofenic acid may increase the anticoagulant activities of Abciximab.
AcenocoumarolTiaprofenic acid may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Acetylsalicylic acid.
AliskirenTiaprofenic acid may decrease the antihypertensive activities of Aliskiren.
AlteplaseTiaprofenic acid may increase the anticoagulant activities of Alteplase.
AmikacinTiaprofenic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAmitriptyline may increase the antiplatelet activities of Tiaprofenic acid.
AnistreplaseTiaprofenic acid may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Apixaban.
ArbekacinTiaprofenic acid may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazideTiaprofenic acid may increase the nephrotoxic activities of Balsalazide.
Citric AcidTiaprofenic acid may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Tiaprofenic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Collagenase.
CyclosporineTiaprofenic acid may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilateTiaprofenic acid may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinTiaprofenic acid may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Tiaprofenic acid.
DeferasiroxThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Tiaprofenic acid.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Tiaprofenic acid.
DicoumarolTiaprofenic acid may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Tiaprofenic acid.
DrospirenoneTiaprofenic acid may increase the hyperkalemic activities of Drospirenone.
Edetic AcidTiaprofenic acid may increase the anticoagulant activities of Edetic Acid.
EnoxaparinTiaprofenic acid may increase the anticoagulant activities of Enoxaparin.
EplerenoneTiaprofenic acid may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetateTiaprofenic acid may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Tiaprofenic acid.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Tiaprofenic acid.
Fondaparinux sodiumTiaprofenic acid may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinTiaprofenic acid may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinTiaprofenic acid may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
GlucosamineGlucosamine may increase the antiplatelet activities of Tiaprofenic acid.
HaloperidolThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Haloperidol.
HeparinTiaprofenic acid may increase the anticoagulant activities of Heparin.
HomoharringtonineThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Homoharringtonine.
HydralazineTiaprofenic acid may decrease the antihypertensive activities of Hydralazine.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tiaprofenic acid.
IcosapentThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Tiaprofenic acid.
KanamycinTiaprofenic acid may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Tiaprofenic acid.
LimaprostLimaprost may increase the antiplatelet activities of Tiaprofenic acid.
LithiumThe serum concentration of Lithium can be increased when it is combined with Tiaprofenic acid.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Tiaprofenic acid.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Tiaprofenic acid.
NadololTiaprofenic acid may decrease the antihypertensive activities of Nadolol.
NeomycinTiaprofenic acid may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinTiaprofenic acid may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
ObinutuzumabThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Tiaprofenic acid.
PamidronateThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Tiaprofenic acid.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Tiaprofenic acid.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Tiaprofenic acid.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Tiaprofenic acid.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Tiaprofenic acid.
PhenindioneTiaprofenic acid may increase the anticoagulant activities of Phenindione.
PhenprocoumonTiaprofenic acid may increase the anticoagulant activities of Phenprocoumon.
PorfimerTiaprofenic acid may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Tiaprofenic acid.
ProbenecidThe serum concentration of Tiaprofenic acid can be increased when it is combined with Probenecid.
ReteplaseTiaprofenic acid may increase the anticoagulant activities of Reteplase.
RibostamycinTiaprofenic acid may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelTiaprofenic acid may increase the anticoagulant activities of Ridogrel.
RivaroxabanTiaprofenic acid may increase the anticoagulant activities of Rivaroxaban.
SparfloxacinTiaprofenic acid may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinTiaprofenic acid may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinaseTiaprofenic acid may increase the anticoagulant activities of Streptokinase.
StreptomycinTiaprofenic acid may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulodexideTiaprofenic acid may increase the anticoagulant activities of Sulodexide.
TacrolimusTiaprofenic acid may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Tiaprofenic acid.
TenecteplaseTiaprofenic acid may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Tenofovir.
TipranavirTipranavir may increase the antiplatelet activities of Tiaprofenic acid.
TobramycinTiaprofenic acid may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideTiaprofenic acid may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Tiaprofenic acid.
TriamtereneTiaprofenic acid may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Tiaprofenic acid.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Tiaprofenic acid.
UrokinaseTiaprofenic acid may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Tiaprofenic acid.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Tiaprofenic acid.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Tiaprofenic acid.
VerteporfinTiaprofenic acid may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Tiaprofenic acid.
WarfarinTiaprofenic acid may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Avoid alcohol.
  • Take with food.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
  3. Brandt KD, Albrecht ME, Kalasinski LA: Effects of tiaprofenic acid on the concentration and metabolism of proteoglycans in normal and degenerating canine articular cartilage. J Clin Pharmacol. 1990 Sep;30(9):808-14. [PubMed:2277128 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [PubMed:14592549 ]
  2. Gupta K, Kaub CJ, Carey KN, Casillas EG, Selinsky BS, Loll PJ: Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorg Med Chem Lett. 2004 Feb 9;14(3):667-71. [PubMed:14741265 ]
  3. Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [PubMed:14987823 ]
  4. Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [PubMed:15575422 ]
Comments
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Drug created on August 29, 2007 12:44 / Updated on September 16, 2013 17:15