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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17652824 |
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. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3582474/ |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
20.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3582474/ |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.55 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8864796/ |
3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
|
7.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
7.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
11.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
8.78 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
76.71 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
65.53 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
77.25 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3582474/ |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
79.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3582474/ |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
35.33 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8864796/ |
3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
|
37.7 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
35.8 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
44.3 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
39.3 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.05 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3582474/ |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3582474/ |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.82 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8864796/ |
3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
|
2.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
2.36 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
2.35 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1748142/ |
3 mg/kg single, intragastric dose: 3 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered: THIOPENTAL |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/301929/ |
TIAPROFENIC ACID serum | Homo sapiens |
||
1.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067848/ |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TIAPROFENIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3% |
TIAPROFENIC ACID plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
2000 mg single, oral Overdose |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
|
400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
|
300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Chronic interstitial cystitis... AEs leading to discontinuation/dose reduction: Chronic interstitial cystitis (grade 3) Sources: |
300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Anorexia, Alkaline phosphatase increased... Other AEs: Lethargy... AEs leading to discontinuation/dose reduction: Anorexia Other AEs:Alkaline phosphatase increased ALT increased GGT increased Lethargy Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Chronic interstitial cystitis | grade 3 Disc. AE |
300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Lethargy | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
ALT increased | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Alkaline phosphatase increased | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Anorexia | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
GGT increased | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes. | 2001 Jun |
|
Effects of some nonsteroidal anti-inflammatory drugs on articular cartilage of rats in an experimental model of osteoarthritis. | 2001 Mar |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
The effect of flurbiprofen and tiaprofenic acid on serum cytokine levels of patients with osteoarthrosis. | 2001 Oct |
|
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 |
|
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 |
|
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)]. | 2002 Oct |
|
The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes. | 2003 Jun 5 |
|
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs. | 2004 Aug 2 |
|
Effects of co-administered dexamethasone and diclofenac potassium on pain, swelling and trismus following third molar surgery. | 2005 Nov 7 |
|
[Patterns of non steroidal anti-inflammatory drug use in ambulatory care]. | 2006 Mar-Apr |
|
Phytalgic, a food supplement, vs placebo in patients with osteoarthritis of the knee or hip: a randomised double-blind placebo-controlled clinical trial. | 2009 |
|
Contact dermatitis due to topical drugs. | 2009 Oct |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2754669
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
Edited
Mon Mar 31 22:12:46 GMT 2025
by
admin
on
Mon Mar 31 22:12:46 GMT 2025
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Record UNII |
ZR3VFO4VD3
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Record Status |
Validated (UNII)
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Record Version |
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-
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Preferred Name | English | ||
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62715-04-2
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6454459
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ZR3VFO4VD3
Created by
admin on Mon Mar 31 22:12:46 GMT 2025 , Edited by admin on Mon Mar 31 22:12:46 GMT 2025
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DTXSID60978337
Created by
admin on Mon Mar 31 22:12:46 GMT 2025 , Edited by admin on Mon Mar 31 22:12:46 GMT 2025
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ACTIVE MOIETY |