DrugBank: Tiaprofenic acid (DB01600)

targets (2)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

2-(5-Benzyl-2-thienyl)propionsaeure
5-Benzoyl-alpha-methyl-2-thiopheneacetic acid
Acide tiaprofenique [inn-french]
Acido tiaprofenico [inn-spanish]
Acidum tiaprofenicum [inn-latin]
Tiaprofensaeure

Brand names

Apo-Tiaprofenic Tablets
Dom-tiaprofenic
Novo-Tiaprofenic
Nu-Tiaprofenic
PMS-tiaprofenic
Surgam
Surgam SR
Tiaprofenic-200 - Tab
Tiaprofenic-300 - Tab

Brand name mixtures

Not Available

Categories

Not Available

CAS number

33005-95-7

Weight

Average: 260.308
Monoisotopic: 260.050714940

Chemical Formula

C₁₄H₁₂O₃S

InChI Key

InChIKey=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)

Plain Text

IUPAC Name

2-(5-benzoylthiophen-2-yl)propanoic acid

SMILES

CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Benzoyl Derivatives

Substructures

Hydroxy Compounds
Acetates
Carboxylic Acids and Derivatives
Benzene and Derivatives
Heterocyclic compounds
Aromatic compounds
Benzoyl Derivatives
Thiophenes
Ketones

Pharmacology

Indication

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

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.

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

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Capsule, extended release	Oral
Tablet	Oral

Prices

Unit description	Cost	Unit
Apo-Tiaprofenic 300 mg Tablet	0.43 USD	tablet
Novo-Tiaprofenic 300 mg Tablet	0.43 USD	tablet
Nu-Tiaprofenic 300 mg Tablet	0.43 USD	tablet
Apo-Tiaprofenic 200 mg Tablet	0.36 USD	tablet
Novo-Tiaprofenic 200 mg Tablet	0.36 USD	tablet

Patents

Not Available

Properties

State

solid

Melting point

96 oC

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	3.24e-02 g/l	ALOGPS
logP	3.22	ALOGPS
logP	3.66	ChemAxon Molconvert
logS	-3.91	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	3	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	54.37	ChemAxon Molconvert
rotatable bond count	4	ChemAxon Molconvert
refractivity	69.19	ChemAxon Molconvert
polarizability	26.78	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	5468
PubChem Substance	46504590
ChemSpider	5269
ChEBI	32221
ChEMBL	32221
Therapeutic Targets Database	DAP000973
PharmGKB	PA10212
Drug Product Database	2136112
Wikipedia	http://en.wikipedia.org/wiki/Tiaprofenic_acid

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Avoid alcohol.
Take with food.

Targets
1. Prostaglandin G/H synthase 2 Pharmacological action: yes Actions: inhibitor May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity Organism class: human UniProt ID: P35354 Gene: PTGS2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed 2. Prostaglandin G/H synthase 1 Pharmacological action: yes Actions: inhibitor May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells Organism class: human UniProt ID: P23219 Gene: PTGS1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. Pubmed 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 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 Hillarp A: [Acetylsalicylic acid resistance—clinical diagnosis with unclear mechanism] Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. Pubmed

Targets

1. Prostaglandin G/H synthase 2

Pharmacological action: yes
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out

Gene: PTGS2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 1

Pharmacological action: yes
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out

Gene: PTGS1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. Pubmed
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
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
Hillarp A: [Acetylsalicylic acid resistance—clinical diagnosis with unclear mechanism] Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. Pubmed

Comments

Drug created on August 29, 2007 12:44 / Updated on April 19, 2011 15:10

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.