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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 ( + / - )

Description

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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.
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.
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

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
Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease.
2001 Apr
Mechanism of lipid peroxidation photosensitized by tiaprofenic acid: product studies using linoleic acid and 1,4-cyclohexadienes as model substrates.
2001 Apr
Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study.
2001 Feb
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
[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
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
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].
2002 Oct
Evaluation of balhimycin as a chiral selector for enantioresolution by capillary electrophoresis.
2004 Aug
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.
2004 Aug 2
In vitro interactions of captopril with NSAID's.
2006 Jul
Effectiveness of conservative treatments for the lumbosacral radicular syndrome: a systematic review.
2007 Jul
Upper gastrointestinal complications associated with NSAIDs in children.
2007 Mar-Apr
Single dose oral tiaprofenic acid for acute postoperative pain in adults.
2009 Oct 7
Patents

Patents

JP2003515526A
462

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%.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:30:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:30:44 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
WHO-ATC M01AE11
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C90908
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
RXCUI
618442
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
ALTERNATIVE
MERCK INDEX
m10847
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY Merck Index
FDA UNII
1LS1T6R34C
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID5023665
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
DRUG CENTRAL
2652
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
CHEBI
32221
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
EVMPD
SUB11011MIG
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
SMS_ID
100000091864
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
MESH
C021270
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
251-329-3
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
INN
3320
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
CAS
33005-95-7
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
DRUG BANK
DB01600
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
WIKIPEDIA
TIAPROFENIC ACID
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
RXCUI
38253
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL365795
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
PUBCHEM
5468
Created by admin on Fri Dec 15 15:30:44 GMT 2023 , Edited by admin on Fri Dec 15 15:30:44 GMT 2023
PRIMARY
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