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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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
22 μg/mL
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
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
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
76.71 μg × h/mL
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
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
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
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
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.77 h
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
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
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
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
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
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
2.1%
TIAPROFENIC ACID serum
Homo sapiens
1.5%
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%
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

Doses

DosePopulationAdverse events​
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
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
Alkaline phosphatase increased
ALT increased
GGT increased
Other AEs:
Lethargy
Sources:
AEs

AEs

AESignificanceDosePopulation
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

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
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
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 Mon Mar 31 22:12:46 GMT 2025
Edited
by admin
on Mon Mar 31 22:12:46 GMT 2025
Record UNII
ZR3VFO4VD3
Record Status Validated (UNII)
Record Version
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Name Type Language
1,3-PROPANEDIOL, 2-AMINO-2-(HYDROXYMETHYL)-, 5-BENZOYL-.ALPHA.-METHYL-2-THIOPHENEACETATE (SALT)
Preferred Name English
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
Code System Code Type Description
CAS
62715-04-2
Created by admin on Mon Mar 31 22:12:46 GMT 2025 , Edited by admin on Mon Mar 31 22:12:46 GMT 2025
PRIMARY
PUBCHEM
6454459
Created by admin on Mon Mar 31 22:12:46 GMT 2025 , Edited by admin on Mon Mar 31 22:12:46 GMT 2025
PRIMARY
FDA UNII
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
PRIMARY
EPA CompTox
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
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY