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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 of TIAPROFENIC ACID

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

Molecular Formula C14H12O3S
Molecular Weight 260.308
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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.
Primary
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.
Palliative
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

PubMed

TitleDatePubMed
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.
1993 Apr
Diclofenac induced hepatitis. 3 cases with features of autoimmune chronic active hepatitis.
1993 Apr
Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs.
1993 Jan
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study.
2001 Feb
[New technologies in laparoscopic surgery].
2001 Mar
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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.
2002 Apr
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
Use of the photo-micronucleus assay in Chinese hamster V79 cells to study photochemical genotoxicity.
2002 Aug 26
[Results of a French nationwide survey of cutaneous side effects of ketoprofen gel reported between September 1996 and August 2000].
2002 Jan-Feb
Do NSAIDs affect the progression of osteoarthritis?
2002 Jun
[Cross-reaction potentials of ketoprofen].
2002 May 12
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].
2002 Oct
Indomethacin-induced morphologic changes in the rat urinary bladder epithelium.
2003 Jan
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
The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes.
2003 Jun 5
Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to non-benzophenone-containing molecules.
2003 Mar
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.
2004 Aug 2
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.
2005 Nov 29
Effects of co-administered dexamethasone and diclofenac potassium on pain, swelling and trismus following third molar surgery.
2005 Nov 7
In vitro interactions of captopril with NSAID's.
2006 Jul
[Patterns of non steroidal anti-inflammatory drug use in ambulatory care].
2006 Mar-Apr
Use of the yeast Saccharomyces cerevisiae as a pre-screening approach for assessment of chemical-induced phototoxicity.
2006 Sep
Activity and potential role of licofelone in the management of osteoarthritis.
2007
The antiplatelet effect of six non-steroidal anti-inflammatory drugs and their pharmacodynamic interaction with aspirin in healthy volunteers.
2008 Apr 1
Cholesterol-diaryl ketone stereoisomeric dyads as models for "clean" type I and type II photooxygenation mechanisms.
2008 Mar 7
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery.
2008 Oct 31
Photodegradation mechanism of nonsteroidal anti-inflammatory drugs containing thiophene moieties: suprofen and tiaprofenic acid.
2009 Aug 13
An exploration of the ability of tepoxalin to ameliorate the degradation of articular cartilage in a canine in vitro model.
2009 Jul 22
Contact dermatitis due to topical drugs.
2009 Oct
Single dose oral tiaprofenic acid for acute postoperative pain in adults.
2009 Oct 7
Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs.
2009 Sep
Hemorrhagic cystitis: A challenge to the urologist.
2010 Apr
Enhancement of antinociception by coadministration of minocycline and a non-steroidal anti-inflammatory drug indomethacin in naïve mice and murine models of LPS-induced thermal hyperalgesia and monoarthritis.
2010 Dec 1
The effect of terpenes on percutaneous absorption of tiaprofenic acid gel.
2010 Nov
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Sample Use Guides

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%.
Substance Class Chemical
Created
by admin
on Fri Dec 16 17:17:48 UTC 2022
Edited
by admin
on Fri Dec 16 17:17:48 UTC 2022
Record UNII
1LS1T6R34C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIAPROFENIC ACID
EP   INN   JAN   MART.   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
NCI_THESAURUS C257
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
WHO-ATC M01AE11
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C90908
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
RXCUI
618442
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
ALTERNATIVE
MERCK INDEX
M10847
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY Merck Index
FDA UNII
1LS1T6R34C
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
EPA CompTox
DTXSID5023665
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
DRUG CENTRAL
2652
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
CHEBI
32221
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
EVMPD
SUB11011MIG
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
MESH
C021270
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
ECHA (EC/EINECS)
251-329-3
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
INN
3320
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
CAS
33005-95-7
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
DRUG BANK
DB01600
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
WIKIPEDIA
TIAPROFENIC ACID
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
RXCUI
38253
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
ChEMBL
CHEMBL365795
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
PUBCHEM
5468
Created by admin on Fri Dec 16 17:17:49 UTC 2022 , Edited by admin on Fri Dec 16 17:17:49 UTC 2022
PRIMARY
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