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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
Hepatotoxicity to several nonsteroidal anti-inflammatory drugs with diclofenac induced histological changes.
1992 Mar
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
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.
2001
Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease.
2001 Apr
Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study.
2001 Feb
Effects of some nonsteroidal anti-inflammatory drugs on articular cartilage of rats in an experimental model of osteoarthritis.
2001 Mar
[New technologies in laparoscopic surgery].
2001 Mar
[Photoaggravated contact allergy and contact photoallergy caused by ketoprofen: 19 cases].
2001 Oct
The effect of flurbiprofen and tiaprofenic acid on serum cytokine levels of patients with osteoarthrosis.
2001 Oct
Photocontact dermatitis to ketoprofen.
2001 Sep
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
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
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.
2003 Jun 2
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.
2004 Aug 2
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
Upper gastrointestinal complications associated with NSAIDs in children.
2007 Mar-Apr
Acute NSAID-related transmural duodenitis and extensive duodenal ulceration.
2007 Nov
The pK(a) Distribution of Drugs: Application to Drug Discovery.
2007 Sep 17
Nitric oxide and cardiovascular effects: new insights in the role of nitric oxide for the management of osteoarthritis.
2008
The antiplatelet effect of six non-steroidal anti-inflammatory drugs and their pharmacodynamic interaction with aspirin in healthy volunteers.
2008 Apr 1
Direct enantioselective HPLC monitoring of lipase-catalyzed kinetic resolution of tiaprofenic acid in nonstandard HPLC organic solvents.
2008 Aug
Cholesterol-diaryl ketone stereoisomeric dyads as models for "clean" type I and type II photooxygenation mechanisms.
2008 Mar 7
Phytalgic, a food supplement, vs placebo in patients with osteoarthritis of the knee or hip: a randomised double-blind placebo-controlled clinical trial.
2009
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 15 15:30:44 UTC 2023
Edited
by admin
on Fri Dec 15 15:30:44 UTC 2023
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 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
WHO-ATC M01AE11
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C90908
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
RXCUI
618442
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
ALTERNATIVE
MERCK INDEX
m10847
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY Merck Index
FDA UNII
1LS1T6R34C
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID5023665
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
DRUG CENTRAL
2652
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
CHEBI
32221
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
EVMPD
SUB11011MIG
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
SMS_ID
100000091864
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
MESH
C021270
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
ECHA (EC/EINECS)
251-329-3
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
INN
3320
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
CAS
33005-95-7
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
DRUG BANK
DB01600
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
WIKIPEDIA
TIAPROFENIC ACID
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
RXCUI
38253
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
ChEMBL
CHEMBL365795
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
PUBCHEM
5468
Created by admin on Fri Dec 15 15:30:44 UTC 2023 , Edited by admin on Fri Dec 15 15:30:44 UTC 2023
PRIMARY
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