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Details

Stereochemistry RACEMIC
Molecular Formula C14H12O3S.C4H11NO3
Molecular Weight 381.443
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIAPROFENIC ACID TROMETAMOL

SMILES

NC(CO)(CO)CO.CC(C(O)=O)C1=CC=C(S1)C(=O)C2=CC=CC=C2

InChI

InChIKey=PDWBZKWQZFGXGU-UHFFFAOYSA-N
InChI=1S/C14H12O3S.C4H11NO3/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10;5-4(1-6,2-7)3-8/h2-9H,1H3,(H,16,17);6-8H,1-3,5H2

HIDE SMILES / InChI

Molecular Formula C4H11NO3
Molecular Weight 121.135
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[Photoaggravated contact allergy and contact photoallergy caused by ketoprofen: 19 cases].
2001 Oct
[Tuberculous osteitis of the malar bone].
2002
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
Fixed drug eruption due to tiaprofenic acid.
2002 Dec
The role of the Australian Adverse Drug Reactions Advisory Committee (ADRAC) in monitoring drug safety.
2002 Dec 27
[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
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.
2003 Jun 2
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
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
Vehicle effects on in vitro release of tiaprofenic acid from different topical formulations.
2004 Jul
The modulation of intra-articular inflammation, cartilage matrix and bone loss in mono-articular arthritis induced by heat-killed Mycobacterium tuberculosis.
2005
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
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
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
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery.
2008 Oct 31
Phytalgic, a food supplement, vs placebo in patients with osteoarthritis of the knee or hip: a randomised double-blind placebo-controlled clinical trial.
2009
Systematic review of the management of canine osteoarthritis.
2009 Apr 4
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 Sat Dec 16 08:37:21 GMT 2023
Edited
by admin
on Sat Dec 16 08:37:21 GMT 2023
Record UNII
ZR3VFO4VD3
Record Status Validated (UNII)
Record Version
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Name Type Language
TIAPROFENIC ACID TROMETAMOL
Common Name English
TROMETHAMINE 5-BENZOYL-.ALPHA.-METHYL-2-THIOPHENEACETATE
Common Name English
2-THIOPHENEACETIC ACID, 5-BENZOYL-.ALPHA.-METHYL-, COMPD. WITH 2-AMINO-2-(HYDROXYMETHYL)-1,3-PROPANEDIOL (1:1)
Systematic Name English
1,3-PROPANEDIOL, 2-AMINO-2-(HYDROXYMETHYL)-, 5-BENZOYL-.ALPHA.-METHYL-2-THIOPHENEACETATE (SALT)
Common Name English
Code System Code Type Description
CAS
62715-04-2
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
PUBCHEM
6454459
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
FDA UNII
ZR3VFO4VD3
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID60978337
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY