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
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
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 |
|---|---|---|---|
Target ID: CHEMBL2094253 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | SURGAM Approved UseSymptomatic 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. |
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| Primary | SURGAM Approved UseSymptomatic 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. |
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| Palliative | SURGAM Approved UseSymptomatic 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 |
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| Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans. | 1993 Apr |
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| Diclofenac induced hepatitis. 3 cases with features of autoimmune chronic active hepatitis. | 1993 Apr |
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| Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. | 1993 Jan |
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| Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries. | 2001 |
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| Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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| Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease. | 2001 Apr |
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| Mechanism of lipid peroxidation photosensitized by tiaprofenic acid: product studies using linoleic acid and 1,4-cyclohexadienes as model substrates. | 2001 Apr |
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| Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study. | 2001 Feb |
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| In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes. | 2001 Jun |
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| Effects of some nonsteroidal anti-inflammatory drugs on articular cartilage of rats in an experimental model of osteoarthritis. | 2001 Mar |
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| [New technologies in laparoscopic surgery]. | 2001 Mar |
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| 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 |
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| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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| 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 |
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| [Photoaggravated contact allergy and contact photoallergy caused by ketoprofen: 19 cases]. | 2001 Oct |
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| The effect of flurbiprofen and tiaprofenic acid on serum cytokine levels of patients with osteoarthrosis. | 2001 Oct |
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| Photocontact dermatitis to ketoprofen. | 2001 Sep |
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| [Tuberculous osteitis of the malar bone]. | 2002 |
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| Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs. | 2002 Apr |
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| 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 |
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| Use of the photo-micronucleus assay in Chinese hamster V79 cells to study photochemical genotoxicity. | 2002 Aug 26 |
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| Fixed drug eruption due to tiaprofenic acid. | 2002 Dec |
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| The role of the Australian Adverse Drug Reactions Advisory Committee (ADRAC) in monitoring drug safety. | 2002 Dec 27 |
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| [Results of a French nationwide survey of cutaneous side effects of ketoprofen gel reported between September 1996 and August 2000]. | 2002 Jan-Feb |
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| Do NSAIDs affect the progression of osteoarthritis? | 2002 Jun |
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| [Cross-reaction potentials of ketoprofen]. | 2002 May 12 |
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| [Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)]. | 2002 Oct |
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| Indomethacin-induced morphologic changes in the rat urinary bladder epithelium. | 2003 Jan |
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| 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 |
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| Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study. | 2003 Jun 2 |
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| The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes. | 2003 Jun 5 |
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| Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to non-benzophenone-containing molecules. | 2003 Mar |
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| Evaluation of balhimycin as a chiral selector for enantioresolution by capillary electrophoresis. | 2004 Aug |
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| Vehicle effects on in vitro release of tiaprofenic acid from different topical formulations. | 2004 Jul |
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| Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population. | 2005 Nov 29 |
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| Effects of co-administered dexamethasone and diclofenac potassium on pain, swelling and trismus following third molar surgery. | 2005 Nov 7 |
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| Activity and potential role of licofelone in the management of osteoarthritis. | 2007 |
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| Effectiveness of conservative treatments for the lumbosacral radicular syndrome: a systematic review. | 2007 Jul |
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| Upper gastrointestinal complications associated with NSAIDs in children. | 2007 Mar-Apr |
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| Cholesterol-diaryl ketone stereoisomeric dyads as models for "clean" type I and type II photooxygenation mechanisms. | 2008 Mar 7 |
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| The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery. | 2008 Oct 31 |
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| Phytalgic, a food supplement, vs placebo in patients with osteoarthritis of the knee or hip: a randomised double-blind placebo-controlled clinical trial. | 2009 |
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| Photodegradation mechanism of nonsteroidal anti-inflammatory drugs containing thiophene moieties: suprofen and tiaprofenic acid. | 2009 Aug 13 |
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| Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs. | 2009 Sep |
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| 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 |
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| The effect of terpenes on percutaneous absorption of tiaprofenic acid gel. | 2010 Nov |
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| 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
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%.
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62715-04-2
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6454459
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ZR3VFO4VD3
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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
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
