TIAPROFENIC ACID

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 Search

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
Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b

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
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17652824	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Arthritis 89 Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b	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.
Pain after injury 2 Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b	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.
Soft-tissue rheumatic conditions 2 Sources: https://mein.sanofi.de/produkte/Surgam/Downloads?id=d7a43169-0340-476a-a43c-1871c227d63b	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

Title	Date	PubMed
Hepatotoxicity to several nonsteroidal anti-inflammatory drugs with diclofenac induced histological changes.	1992 Mar	1582111
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.	1993 Apr	8517101
Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs.	1993 Jan	8423545
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
[Photoaggravated contact allergy and contact photoallergy caused by ketoprofen: 19 cases].	2001 Oct	11907961
[Tuberculous osteitis of the malar bone].	2002	12616953
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.	2002 Apr	12147041
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	12234061
Use of the photo-micronucleus assay in Chinese hamster V79 cells to study photochemical genotoxicity.	2002 Aug 26	12160891
Fixed drug eruption due to tiaprofenic acid.	2002 Dec	19753743
The role of the Australian Adverse Drug Reactions Advisory Committee (ADRAC) in monitoring drug safety.	2002 Dec 27	12505292
[Results of a French nationwide survey of cutaneous side effects of ketoprofen gel reported between September 1996 and August 2000].	2002 Jan-Feb	12090148
Do NSAIDs affect the progression of osteoarthritis?	2002 Jun	12083420
[Cross-reaction potentials of ketoprofen].	2002 May 12	12063858
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].	2002 Oct	12442124
Indomethacin-induced morphologic changes in the rat urinary bladder epithelium.	2003 Jan	12559315
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	12884398
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.	2003 Jun 2	12771981
The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes.	2003 Jun 5	12791169
Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to non-benzophenone-containing molecules.	2003 Mar	12755728
Evaluation of balhimycin as a chiral selector for enantioresolution by capillary electrophoresis.	2004 Aug	15351999
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.	2004 Aug 2	15226764
Vehicle effects on in vitro release of tiaprofenic acid from different topical formulations.	2004 Jul	15231433
The modulation of intra-articular inflammation, cartilage matrix and bone loss in mono-articular arthritis induced by heat-killed Mycobacterium tuberculosis.	2005	16259721
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.	2005 Nov 29	16316472
Effects of co-administered dexamethasone and diclofenac potassium on pain, swelling and trismus following third molar surgery.	2005 Nov 7	16274480
In vitro interactions of captopril with NSAID's.	2006 Jul	16935827
[Patterns of non steroidal anti-inflammatory drug use in ambulatory care].	2006 Mar-Apr	16886702
Use of the yeast Saccharomyces cerevisiae as a pre-screening approach for assessment of chemical-induced phototoxicity.	2006 Sep	16497474
Activity and potential role of licofelone in the management of osteoarthritis.	2007	18044077
Effectiveness of conservative treatments for the lumbosacral radicular syndrome: a systematic review.	2007 Jul	17415595
Upper gastrointestinal complications associated with NSAIDs in children.	2007 Mar-Apr	17582320
Acute NSAID-related transmural duodenitis and extensive duodenal ulceration.	2007 Nov	18158085
The pK(a) Distribution of Drugs: Application to Drug Discovery.	2007 Sep 17	19812734
Nitric oxide and cardiovascular effects: new insights in the role of nitric oxide for the management of osteoarthritis.	2008	19007428
The antiplatelet effect of six non-steroidal anti-inflammatory drugs and their pharmacodynamic interaction with aspirin in healthy volunteers.	2008 Apr 1	18359332
Direct enantioselective HPLC monitoring of lipase-catalyzed kinetic resolution of tiaprofenic acid in nonstandard HPLC organic solvents.	2008 Aug	18246593
Cholesterol-diaryl ketone stereoisomeric dyads as models for "clean" type I and type II photooxygenation mechanisms.	2008 Mar 7	18292877
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery.	2008 Oct 31	18972594
Phytalgic, a food supplement, vs placebo in patients with osteoarthritis of the knee or hip: a randomised double-blind placebo-controlled clinical trial.	2009	20015358
Systematic review of the management of canine osteoarthritis.	2009 Apr 4	19346540
Photodegradation mechanism of nonsteroidal anti-inflammatory drugs containing thiophene moieties: suprofen and tiaprofenic acid.	2009 Aug 13	19719267
An exploration of the ability of tepoxalin to ameliorate the degradation of articular cartilage in a canine in vitro model.	2009 Jul 22	19624842
Contact dermatitis due to topical drugs.	2009 Oct	19834431
Single dose oral tiaprofenic acid for acute postoperative pain in adults.	2009 Oct 7	19821426
Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs.	2009 Sep	19740398
Hemorrhagic cystitis: A challenge to the urologist.	2010 Apr	20877590
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	21122103
The effect of terpenes on percutaneous absorption of tiaprofenic acid gel.	2010 Nov	21116781
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

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

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Name

Type

Language

TIAPROFENIC ACID

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