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Details

Stereochemistry ACHIRAL
Molecular Formula C16H19FN2O3S
Molecular Weight 338.397
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TILMACOXIB

SMILES

CC1=NC(C2CCCCC2)=C(O1)C3=CC=C(C(F)=C3)S(N)(=O)=O

InChI

InChIKey=MIMJSJSRRDZIPW-UHFFFAOYSA-N
InChI=1S/C16H19FN2O3S/c1-10-19-15(11-5-3-2-4-6-11)16(22-10)12-7-8-14(13(17)9-12)23(18,20)21/h7-9,11H,2-6H2,1H3,(H2,18,20,21)

HIDE SMILES / InChI
Molecular Formula C16H19FN2O3S
Molecular Weight 338.397
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800009145 and http://www.genome.jp/dbget-bin/www_bget?dr:D01974

Tilmacoxib [JTE 522] is an orally active, potent and highly selective cyclo-oxygenase-2 (COX-2) inhibitor. It entered phase II clinical trials for the treatment of Familial adenomatous polyposis, rheumatoid arthritis, osteoarthritis, and acute pain in Japan, but was discontinued in 2003.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 85.0 nM [IC50]
Hepatocellular carcinoma cells growth
1
Target ID: Hepatocellular carcinoma cells growth
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60.9 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TILMACOXIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
2.9 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TILMACOXIB blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
325 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TILMACOXIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
20445 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TILMACOXIB blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8.5 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TILMACOXIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
130.6 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TILMACOXIB blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
7.83 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TILMACOXIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
925.3 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TILMACOXIB blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TILMACOXIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
12.62 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TILMACOXIB blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
40.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12445023/
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TILMACOXIB blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
Other AEs: Cold, Diarrhea...
Other AEs:
Cold (6 patients)
Diarrhea (8 patients)
Stomachache (3 patients)
Hemoglobin decreased (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
AEs

AEs

AESignificanceDosePopulation
Hemoglobin decreased 2 patients
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
Stomachache 3 patients
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
Cold 6 patients
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
Diarrhea 8 patients
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16622748/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

CYP1A2
2153
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no
CYP2D6
2546
 yes [IC50 13.8029 uM]
CYP3A4
2633
 yes [IC50 15.4871 uM]
CYP2C9
2497
 yes [IC50 2.1876 uM]
CYP2C19
2141
 yes [IC50 38.9018 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Preventive effect of JTE-522, a selective cyclooxygenase-2 inhibitor, on DEN-induced hepatocarcinogenesis in rats.
2010-05
Enhancement of the sensitivity of renal cell carcinoma cells to fas-mediated cytotoxicity and apoptosis by the selective cyclooxygenase-2 inhibitor JTE-522.
2010
Mechanisms of anti-proliferative effect of JTE-522, a selective cyclooxygenase-2 inhibitor, on human liver cancer cells.
2007-11
Selective cyclooxygenase-2 inhibitor downregulates the paracrine epithelial-mesenchymal interactions of growth in scirrhous gastric carcinoma.
2007-02-01
A synergic inhibitory-effect of combination with selective cyclooxygenase-2 inhibitor and S-1 on the peritoneal metastasis for scirrhous gastric cancer cells.
2006-12-08
Bilateral induction of the S-100A9 gene in response to spreading depression is modulated by the cyclooxygenase-2 activity.
2005-07-15
Inhibitory effect of a selective cyclooxygenase inhibitor on the invasion-stimulating activity of orthotopic fibroblasts for scirrhous gastric cancer cells.
2005-07
JTE-522, a selective COX-2 inhibitor, inhibits growth of pulmonary metastases of colorectal cancer in rats.
2005-03-03
Selective inhibition of cyclooxygenase (COX)-2 inhibits endothelial cell proliferation by induction of cell cycle arrest.
2005-02-10
Selective inhibition of cyclooxygenase-2 inhibits colon cancer cell adhesion to extracellular matrix by decreased expression of beta1 integrin.
2005-02
JTE-522, a selective cyclooxygenase-2 inhibitor, inhibits induction but not growth and invasion of 1,2-dimethylhydrazine-induced tubular adenocarcinomas of colon in rats.
2005-01-20
JTE-522, a selective COX-2 inhibitor, interferes with the growth of lung metastases from colorectal cancer in rats due to inhibition of neovascularization: a vascular cast model study.
2004-12-20
Cyclooxygenase-2 gene induction causes CDDP resistance in colon cancer cell line, HCT-15.
2004-11-03
Enhanced sensitivity of bladder cancer cells to cisplatin mediated cytotoxicity and apoptosis in vitro and in vivo by the selective cyclooxygenase-2 inhibitor JTE-522.
2004-10
Inhibition of azoxymethane-induced colon carcinogenesis in rats due to JTE-522, a selective cyclooxygenase-2 inhibitor.
2004-09-18
Production of prostaglandinE2 via bile acid is enhanced by trypsin and acid in normal human esophageal epithelial cells.
2004-05-21
Chemopreventive effect of JTE-522, a selective cyclooxygenase-2 inhibitor, on 1, 2-dimethylhydrazine-induced rat colon carcinogenesis.
2003-12-08
COX-2/VEGF-dependent facilitation of tumor-associated angiogenesis and tumor growth in vivo.
2003-10
Combination chemotherapy with JTE-522, a novel selective cyclooxygenase-2 inhibitor, and cisplatin against gastric cancer cell lines in vitro and in vivo.
2003-08-22
JTE-522, a cyclooxygenase-2 inhibitor, is an effective chemopreventive agent against rat experimental liver fibrosis1.
2003-08
The potential for a selective cyclooxygenase-2 inhibitor in the prevention of liver metastasis in human colorectal cancer.
2003-04-12
Suppression of pancreatic cancer cell invasion by a cyclooxygenase-2-specific inhibitor.
2003
Synergistic cytotoxicity and apoptosis of JTE-522, a selective cyclooxygenase-2 inhibitor, and 5-fluorouracil against bladder cancer.
2002-12
Pharmacokinetics and safety of JTE-522, a novel selective cyclooxygenase-2 inhibitor, in healthy male volunteers.
2002-11
Inhibitory effect of a selective cyclooxygenase-2 inhibitor on liver metastasis of colon cancer.
2002-08-10
Significant growth inhibition of human lung cancer cells both in vitro and in vivo by the combined use of a selective cyclooxygenase 2 inhibitor, JTE-522, and conventional anticancer agents.
2002-07
JTE-522, a selective COX-2 inhibitor, inhibits cell proliferation and induces apoptosis in RL95-2 cells.
2002-07
Changes of NF-kB, p53, Bcl-2 and caspase in apoptosis induced by JTE-522 in human gastric adenocarcinoma cell line AGS cells: role of reactive oxygen species.
2002-06
Inhibition of proliferation of gastric epithelial cells by a cyclooxygenase 2 inhibitor, JTE522, is also mediated by a PGE2-independent pathway.
2002-04
JTE-522-induced apoptosis in human gastric adenocarcinoma [correction of adenocarcinoma] cell line AGS cells by caspase activation accompanying cytochrome C release, membrane translocation of Bax and loss of mitochondrial membrane potential.
2002-04
4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522(1).
2002-03-28
Prostacyclin synthase gene transfer modulates cyclooxygenase-2-derived prostanoid synthesis and inhibits neointimal formation in rat balloon-injured arteries.
2002-02-01
Cyclooxygenase-2 downregulates inducible nitric oxide synthase in rat intestinal epithelial cells.
2001-09
Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by JTE-522, a selective COX-2 inhibitor.
2001-04
Cyclooxygenase-2 stimulates production of amyloid beta-peptide in neuroblastoma x glioma hybrid NG108-15 cells.
2001-02-23
Patents

Patents

US2015297747
1
US2016067241
1
US2016074337
1

Sample Use Guides

In Vivo Use Guide
50 mg or 200 mg, once daily orally for 26 weeks.
Route of Administration: Oral
In Vitro Use Guide
Escalating doses (100 nM to 100 uM) of Tilmacoxib (JTE-522) significantly inhibited the growth of all HCC cells in a dose- and time-dependent manner.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:08:31 GMT 2025
Edited
by admin
on Mon Mar 31 18:08:31 GMT 2025
Record UNII
G6VI5P84SX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JTE-522
Preferred Name English
TILMACOXIB
INN   JAN   USAN  
USAN   INN  
Official Name English
TILMACOXIB [USAN]
Common Name English
JTP-19605
Code English
RWJ-57504
Code English
TILMACOXIB [JAN]
Common Name English
BENZENESULFONAMIDE, 4-(4-CYCLOHEXYL-2-METHYL-5-OXAZOLYL)-2-FLUORO-
Systematic Name English
4-(4-Cyclohexyl-2-methyloxazol-5-yl)-2-fluorobenzenesulfonamide
Systematic Name English
tilmacoxib [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
Code System Code Type Description
INN
8033
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
NCI_THESAURUS
C76640
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
USAN
MM-67
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
PUBCHEM
159271
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL34913
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
FDA UNII
G6VI5P84SX
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
CHEBI
73041
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID0057671
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
CAS
180200-68-4
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
SMS_ID
300000034365
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
WIKIPEDIA
Tilmacoxib
Created by admin on Mon Mar 31 18:08:31 GMT 2025 , Edited by admin on Mon Mar 31 18:08:31 GMT 2025
PRIMARY
Related Record Type Details
COX-2
TARGET -> INHIBITOR
Related Record Type Details
Structure of TILMACOXIB
ACTIVE MOIETY
NIH
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