TIAPROFENIC ACID

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H12O3S
Molecular Weight	260.308
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC=C(S1)C(=O)C2=CC=CC=C2

InChI

InChIKey=GUHPRPJDBZHYCJ-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b

Tiaprofenic acid is a non-steroidal, anti-inflammatory, analgesic compound, which nonselectively inhibits cyclooxygenase protein. Tiaprofenic acid was approved in Europe for the symptomatic relief of arthritis, ankylosing spondylitis and other inflammatory-rheumatic disorders as well as the painful conditions after injury.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17652824	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Arthritis 89 Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b	Palliative	Approved 8429	SURGAM Approved Use Symptomatic treatment of pain and inflammation in acute arthritis (including gout attack), chronic arthritis (rheumatoid arthritis in particular), ankylosing spondylitis and other inflammatory-rheumatic spinal disorders, irritation in degenerative joint and spine diseases (arthritis and spondylarthritis), inflammatory soft tissue rheumatic diseases, painful swelling or inflammation after injury.
Pain after injury 2 Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b	Primary	Approved 8429	SURGAM Approved Use Symptomatic treatment of pain and inflammation in acute arthritis (including gout attack), chronic arthritis (rheumatoid arthritis in particular), ankylosing spondylitis and other inflammatory-rheumatic spinal disorders, irritation in degenerative joint and spine diseases (arthritis and spondylarthritis), inflammatory soft tissue rheumatic diseases, painful swelling or inflammation after injury.
Soft-tissue rheumatic conditions 2 Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b	Palliative	Approved 8429	SURGAM Approved Use Symptomatic treatment of pain and inflammation in acute arthritis (including gout attack), chronic arthritis (rheumatoid arthritis in particular), ankylosing spondylitis and other inflammatory-rheumatic spinal disorders, irritation in degenerative joint and spine diseases (arthritis and spondylarthritis), inflammatory soft tissue rheumatic diseases, painful swelling or inflammation after injury.

PubMed

Title	Date	PubMed
Hepatotoxicity to several nonsteroidal anti-inflammatory drugs with diclofenac induced histological changes.	1992 Mar	1582111
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.	1993 Apr	8517101
Diclofenac induced hepatitis. 3 cases with features of autoimmune chronic active hepatitis.	1993 Apr	8462374
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease.	2001 Apr	11394653
Mechanism of lipid peroxidation photosensitized by tiaprofenic acid: product studies using linoleic acid and 1,4-cyclohexadienes as model substrates.	2001 Apr	11332030
Effects of some nonsteroidal anti-inflammatory drugs on articular cartilage of rats in an experimental model of osteoarthritis.	2001 Mar	11426673
[New technologies in laparoscopic surgery].	2001 Mar	11317443
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.	2001 May-Jun	11386636
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Antibodies directed to drug epitopes to investigate the structure of drug-protein photoadducts. Recognition of a common photobound substructure in tiaprofenic acid/ketoprofen cross-photoreactivity.	2001 Nov	11712905
Photocontact dermatitis to ketoprofen.	2001 Sep	11526526
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.	2002 Apr	12147041
Differential effects of nonsteroidal antiinflammatory drugs on the IL-1 altered expression of plasminogen activators and plasminogen activator inhibitor-1 by articular chondrocytes.	2002 Aug	12234061
Fixed drug eruption due to tiaprofenic acid.	2002 Dec	19753743
The role of the Australian Adverse Drug Reactions Advisory Committee (ADRAC) in monitoring drug safety.	2002 Dec 27	12505292
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].	2002 Oct	12442124
Thin layer chromatographic resolution of some 2-arylpropionic acid enantiomers using L-(-)-serine, L-(-)-threonine and a mixture of L-(-)-serine and L-(-)-threonine-impregnated silica gel as stationary phases.	2003 Jul	12884398
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.	2003 Jun 2	12771981
Vehicle effects on in vitro release of tiaprofenic acid from different topical formulations.	2004 Jul	15231433
Effectiveness of conservative treatments for the lumbosacral radicular syndrome: a systematic review.	2007 Jul	17415595
The antiplatelet effect of six non-steroidal anti-inflammatory drugs and their pharmacodynamic interaction with aspirin in healthy volunteers.	2008 Apr 1	18359332
Cholesterol-diaryl ketone stereoisomeric dyads as models for "clean" type I and type II photooxygenation mechanisms.	2008 Mar 7	18292877
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery.	2008 Oct 31	18972594
Phytalgic, a food supplement, vs placebo in patients with osteoarthritis of the knee or hip: a randomised double-blind placebo-controlled clinical trial.	2009	20015358
Contact dermatitis due to topical drugs.	2009 Oct	19834431
The effect of terpenes on percutaneous absorption of tiaprofenic acid gel.	2010 Nov	21116781

Patents

Sample Use Guides

In Vivo Use Guide

The recommended daily dose range for adults is 600 mg tiaprofen acid per day divided into 2 doses.

Route of Administration: Oral

In Vitro Use Guide

Human osteoarthritic cartilage was treated with therapeutic doses of tiaprofenic acid (26 micrograms/ml; 2.6 micrograms/ml) in order to test the effect of the drug on the proteoglycan metabolism (catabolism and synthesis) and chondrocyte ultrastructure. The drug suppresed the proteoglycan metabolism by 38%.

Name

Type

Language

TIAPROFENIC ACID

Official Name

English

TIAPROFEN

Brand Name

English

SURGAM

Brand Name

English

Tiaprofenic acid [WHO-DD]

Common Name

English

TIAPROFENATE

Common Name

English

tiaprofenic acid [INN]

Common Name

English

5-BENZOYL-.ALPHA.-METHYL-2-THIOPHENEACETIC ACID

Systematic Name

English

TIAPROFENIC ACID [MI]

Common Name

English

RU-15060

Code

English

TIAPROFENIC ACID [MART.]

Common Name

English

TIAPROFENIC ACID [JAN]

Common Name

English

TIAPROFENIC ACID [EP IMPURITY]

Common Name

English

TIAPROFENIC ACID [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM01AE11