Identification
- Summary
Tiaprofenic acid is a nonsteroidal anti-inflammatory (NSAID) used to manage inflammation and analgesia associated with rheumatoid arthritis and osteoarthritis.
- Generic Name
- Tiaprofenic acid
- DrugBank Accession Number
- DB01600
- Background
Tiaprofenic acid is a non-steroidal anti-inflammatory drug employed in the treatment of pain, particularly arthritis pain. It belongs to the arylpropionic acid (profen) group of nonsteroidal anti-inflammatory drugs (NSAIDs).
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tiaprofenic acid (DB01600)
- Weight
- Average: 260.308
Monoisotopic: 260.05071494 - Chemical Formula
- C14H12O3S
- Synonyms
- 2-(5-Benzoyl-thiophen-2-yl)-propionic acid
- 2-(5-Benzyl-2-thienyl)propionsäure
- 5-benzoyl-α-methyl-2-thiopheneacetic acid
- 5-benzoyl-α-methylthiophene-2-acetic acid
- Acide tiaprofenique
- Acido tiaprofenico
- Acidum tiaprofenicum
- Tiaprofenic acid
- Tiaprofensäure
- α-methyl-5-benzoyl-2-thienylacetic acid
Pharmacology
- Indication
Tiaprofenic acid is used to treat pain, especially arthritic pain.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Osteoarthritis •••••••••••• Symptomatic treatment of Rheumatoid arthritis •••••••••••• - Contraindications & Blackbox Warnings
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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. This drug is not recommended for use in the pediatric population.
- 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.
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Tiaprofenic Acid Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Tiaprofenic acid may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Tiaprofenic acid is combined with Abciximab. Acebutolol Tiaprofenic acid may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Acemetacin. - Food Interactions
- Avoid alcohol.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Surgamyl
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Albert Tiafen SR Capsule, extended release 300 mg Oral Aventis Pharma Ltd. Not applicable Not applicable Canada 
Albert Tiafen Tab 200mg Tablet 200 mg Oral Aventis Pharma Ltd. 1991-12-31 2004-07-30 Canada Albert Tiafen Tab 300mg Tablet 300 mg Oral Aventis Pharma Ltd. 1991-12-31 2004-07-30 Canada Surgam Tablet 300 mg Oral Sanofi Aventis 1997-08-20 2007-11-22 Canada Surgam SR Capsule, extended release 300 mg Oral Sanofi Aventis 1997-02-21 2007-07-31 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-tiaprofenic Tablets -300mg Tablet 300 mg Oral Apotex Corporation 1994-12-31 Not applicable Canada Apo-tiaprofenic Tablets-200mg Tablet 200 mg Oral Apotex Corporation 1994-12-31 Not applicable Canada Dom-tiaprofenic Tablet 200 mg / tab Oral Dominion Pharmacal Not applicable Not applicable Canada Dom-tiaprofenic Tablet 300 mg Oral Dominion Pharmacal 2000-06-20 2023-05-08 Canada Nu-tiaprofenic - Tab 200mg Tablet 200 mg Oral Nu Pharm Inc 1995-12-31 2012-09-04 Canada
Categories
- ATC Codes
- M01AE11 — Tiaprofenic acid
- Drug Categories
- Acids, Acyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Fatty Acids
- Fatty Acids, Volatile
- Lipids
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Other Nonsteroidal Anti-inflammatory Agents
- Peripheral Nervous System Agents
- Photosensitizing Agents
- Propionates
- Prostaglandin Antagonists
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- 2,5-disubstituted thiophene / Aromatic heteromonocyclic compound / Aryl-phenylketone / Benzenoid / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid, thiophenes, aromatic ketone (CHEBI:32221)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1LS1T6R34C
- CAS number
- 33005-95-7
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015538
- PubChem Compound
- 5468
- PubChem Substance
- 46504590
- ChemSpider
- 5269
- BindingDB
- 223313
- 38253
- ChEBI
- 32221
- ChEMBL
- CHEMBL365795
- Therapeutic Targets Database
- DAP000973
- PharmGKB
- PA164764503
- Wikipedia
- Tiaprofenic_acid
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count Not Available Completed Treatment Osteoarthritis of the Knee 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suppository Tablet Oral Tablet Oral 300.000 mg Capsule, extended release Oral 300 mg Tablet Oral 200 mg / tab Tablet Oral 300 mg / tab Capsule, extended release Oral 300 mg / cap Granule, for solution Oral 300 MG Injection, powder, for solution Intramuscular 200 MG/3ML Suppository 300 MG Tablet Oral 200 mg Tablet Oral 300 mg Granule - Prices
Unit description Cost Unit Apo-Tiaprofenic 300 mg Tablet 0.43USD tablet Novo-Tiaprofenic 300 mg Tablet 0.43USD tablet Nu-Tiaprofenic 300 mg Tablet 0.43USD tablet Apo-Tiaprofenic 200 mg Tablet 0.36USD tablet Novo-Tiaprofenic 200 mg Tablet 0.36USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 96 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0324 mg/mL ALOGPS logP 3.22 ALOGPS logP 3.66 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 4.03 Chemaxon pKa (Strongest Basic) -7.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.37 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 69.19 m3·mol-1 Chemaxon Polarizability 26.78 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9927 Blood Brain Barrier + 0.9289 Caco-2 permeable + 0.6039 P-glycoprotein substrate Non-substrate 0.7298 P-glycoprotein inhibitor I Non-inhibitor 0.9534 P-glycoprotein inhibitor II Non-inhibitor 0.9664 Renal organic cation transporter Non-inhibitor 0.8998 CYP450 2C9 substrate Non-substrate 0.6293 CYP450 2D6 substrate Non-substrate 0.9226 CYP450 3A4 substrate Non-substrate 0.8098 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.8607 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.8958 CYP450 3A4 inhibitor Non-inhibitor 0.9526 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.9398 Carcinogenicity Non-carcinogens 0.7568 Biodegradation Ready biodegradable 0.7714 Rat acute toxicity 3.1892 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9869 hERG inhibition (predictor II) Non-inhibitor 0.9716
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 167.6020316 predictedDarkChem Lite v0.1.0 [M-H]- 156.43575 predictedDeepCCS 1.0 (2019) [M+H]+ 168.9192316 predictedDarkChem Lite v0.1.0 [M+H]+ 158.8119 predictedDeepCCS 1.0 (2019) [M+Na]+ 168.0560316 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.88689 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [Article]
- 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. [Article]
- 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. [Article]
- Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at August 29, 2007 18:44 / Updated at February 20, 2024 23:55