Identification

Name
Tiaprofenic acid
Accession Number
DB01600
Type
Small Molecule
Groups
Approved
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Albert Tiafen SRCapsule, extended release300 mgOralAventis Pharma Ltd.Not applicableNot applicableCanada
Albert Tiafen Tab 200mgTablet200 mgOralAventis Pharma Ltd.1991-12-312004-07-30Canada
Albert Tiafen Tab 300mgTablet300 mgOralAventis Pharma Ltd.1991-12-312004-07-30Canada
SurgamTablet300 mgOralSanofi Aventis1997-08-202007-11-22Canada
Surgam SRCapsule, extended release300 mgOralSanofi Aventis1997-02-212007-07-31Canada
Surgam SR Cap 300mgCapsule, extended release300 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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tiaprofenic Tablets -300mgTablet300 mgOralApotex Corporation1994-12-31Not applicableCanada
Apo-tiaprofenic Tablets-200mgTablet200 mgOralApotex Corporation1994-12-31Not applicableCanada
Dom-tiaprofenicTablet200 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-tiaprofenicTablet300 mgOralDominion Pharmacal2000-06-20Not 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
International/Other Brands
Surgamyl
Categories
UNII
1LS1T6R34C
CAS number
33005-95-7
Weight
Average: 260.308
Monoisotopic: 260.05071494
Chemical Formula
C14H12O3S
InChI Key
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

Pharmacology

Indication

Tiaprofenic acid is used to treat pain, especially arthritic pain.

Associated Conditions
Pharmacodynamics

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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
AProstaglandin G/H synthase 1
inhibitor
Human
Absorption

Bioavailability is 90% following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

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

Route of elimination
Not Available
Half life

1.5-2.5 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tiaprofenic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Tiaprofenic acid is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Tiaprofenic acid is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Tiaprofenic acid is combined with 4-hydroxycoumarin.
AbacavirTiaprofenic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Tiaprofenic acid is combined with Abciximab.
AcarboseTiaprofenic acid may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololTiaprofenic acid may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Acemetacin.
AcenocoumarolThe risk or severity of gastrointestinal bleeding can be increased when Tiaprofenic acid is combined with Acenocoumarol.
Food Interactions
  • Avoid alcohol.
  • Take with food.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015538
PubChem Compound
5468
PubChem Substance
46504590
ChemSpider
5269
BindingDB
223313
ChEBI
32221
ChEMBL
CHEMBL365795
Therapeutic Targets Database
DAP000973
PharmGKB
PA164764503
Wikipedia
Tiaprofenic_acid
ATC Codes
M01AE11 — Tiaprofenic acid
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Capsule, extended releaseOral300 mg
TabletOral200 mg
TabletOral300 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)96 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a5i-3910000000-04c8e1561815c7f17b73

Taxonomy

Description
This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl-phenylketones
Alternative Parents
Thiophene carboxylic acids and derivatives / Benzoyl derivatives / 2,5-disubstituted thiophenes / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Aryl-phenylketone / Thiophene carboxylic acid or derivatives / Benzoyl / 2,5-disubstituted thiophene / Benzenoid / Monocyclic benzene moiety / Heteroaromatic compound / Thiophene / Organoheterocyclic compound / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid, thiophenes, aromatic ketone (CHEBI:32221)

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...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
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]

Drug created on August 29, 2007 12:44 / Updated on November 12, 2018 07:30