Compound Detail
CHEMBL408
TROGLITAZONE 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL408 |
| Name | TROGLITAZONE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | GXPHKUHSUJUWKP-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
45
Targets
101
Activities
3
Assay Types
30
PK Parameters
20
Publications
9
Known Names
2
Indications
1
Mechanisms
Molecular Properties
441.6
MW (Da)
4.37
ALogP
6
HBA
2
HBD
84.9
PSA (Ų)
0.72
QED
0
Ro5 Violations
5
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1997 |
| Availability | Withdrawn |
| Chirality | Racemic |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Peroxisome proliferator-activated receptor gamma agonist | AGONIST | Peroxisome proliferator-activated receptor gamma | ✓ | ✓ |
Indications
Diabetes Mellitus Sarcoma
ATC Classification
A10BG01
troglitazone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES
Drug Warnings
Withdrawn
hepatotoxicity
hepatic necrosis and failure, with a mean time to onset of 3 months.
Withdrawn
hepatotoxicity
hepatic necrosis and failure, with a mean time to onset of 3 months.
Withdrawn
hepatotoxicity
Hepatotoxicity
Withdrawn
hepatotoxicity
Severe hepatic adverse effects
Withdrawn
hepatotoxicity
hepatic necrosis and failure, with a mean time to onset of 3 months.
Withdrawn
hepatotoxicity
Severe hepatic adverse effects
Withdrawn
hepatotoxicity
Hepatotoxicity
Withdrawn
hepatotoxicity
hepatic necrosis and failure, with a mean time to onset of 3 months.
Activity Summary
IC50 58 meas. best 7.27
EC50 29 meas. best 7.0
Ki 14 meas. best 7.28
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Forkhead box protein M1 CHEMBL4739852 | Ki | 7.28 | 7.28 | 52.0 | 1 |
| Liver CHEMBL613642 | IC50 | 7.27 | 7.27 | 53.2 | 1 |
| Mesenchymal stem cells CHEMBL5058627 | EC50 | 7.0 | 7.0 | 100.0 | 1 |
| 3T3-L1 CHEMBL614510 | EC50 | 6.89 | 6.89 | 130.0 | 2 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | Ki | 6.7 | 6.33 | 200.0 | 6 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | EC50 | 6.67 | 6.0855 | 215.0 | 20 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | IC50 | 6.52 | 6.13 | 300.0 | 6 |
| Peroxisome proliferator-activated receptor gamma CHEMBL2459 | EC50 | 6.11 | 6.055 | 780.0 | 2 |
| Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456 | IC50 | 6.1 | 6.1 | 800.0 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | Ki | 6.08 | 6.08 | 835.0 | 1 |
| Unchecked CHEMBL612545 | EC50 | 6.07 | 6.07 | 860.0 | 1 |
| Carbonic anhydrase 2 CHEMBL205 | IC50 | 6.01 | 6.01 | 970.0 | 1 |
| Mitogen-activated protein kinase 1 CHEMBL4040 | IC50 | 5.91 | 5.91 | 1238.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 5.89 | 5.3314 | 1299.3 | 7 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | IC50 | 5.88 | 5.88 | 1312.0 | 1 |
| Aldo-keto reductase family 1 member B1 CHEMBL2622 | IC50 | 5.69 | 5.69 | 2038.0 | 1 |
| Amine oxidase [flavin-containing] B CHEMBL2039 | IC50 | 5.68 | 5.68 | 2070.0 | 2 |
| Bile salt export pump CHEMBL6020 | IC50 | 5.57 | 5.16 | 2700.0 | 7 |
| Thromboxane-A synthase CHEMBL1835 | IC50 | 5.53 | 5.53 | 2966.0 | 1 |
| Adenosine receptor A3 CHEMBL256 | Ki | 5.53 | 5.53 | 2943.0 | 1 |
| Bile salt export pump CHEMBL2073674 | IC50 | 5.41 | 5.19 | 3900.0 | 2 |
| Cytochrome P450 2C9 CHEMBL3397 | IC50 | 5.4 | 5.4 | 4000.0 | 1 |
| Leishmania donovani CHEMBL367 | IC50 | 5.37 | 5.37 | 4260.0 | 1 |
| Indoleamine 2,3-dioxygenase 2 CHEMBL2189159 | IC50 | 5.35 | 5.35 | 4500.0 | 1 |
| Amine oxidase [flavin-containing] A CHEMBL3358 | Ki | 5.32 | 5.32 | 4800.0 | 1 |
| Adenosine receptor A3 CHEMBL256 | IC50 | 5.28 | 5.28 | 5208.0 | 1 |
| Nuclear receptor subfamily 1 group I member 2 CHEMBL3401 | EC50 | 5.16 | 4.9033 | 6900.0 | 3 |
| Plasmodium falciparum CHEMBL364 | IC50 | 5.14 | 5.14 | 7270.0 | 1 |
| Amine oxidase [flavin-containing] B CHEMBL2039 | Ki | 5.02 | 5.02 | 9500.0 | 1 |
| Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762 | IC50 | 5.02 | 5.02 | 9500.0 | 1 |
| Hepatitis B virus CHEMBL613497 | IC50 | 5.0 | 5.0 | 10000.0 | 1 |
| Amine oxidase [flavin-containing] A CHEMBL1951 | Ki | 4.98 | 4.98 | 10500.0 | 1 |
| Amine oxidase [flavin-containing] B CHEMBL2993 | Ki | 4.96 | 4.96 | 10900.0 | 1 |
| PC-12 CHEMBL612556 | IC50 | 4.82 | 4.82 | 15000.0 | 1 |
| MDA-MB-231 CHEMBL400 | IC50 | 4.8 | 4.57 | 15700.0 | 2 |
| Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL3259476 | IC50 | 4.7 | 4.7 | 20000.0 | 1 |
| UDP-glucuronosyltransferase 1-6 CHEMBL1743316 | Ki | 4.7 | 4.7 | 20000.0 | 1 |
| LNCaP CHEMBL612518 | IC50 | 4.66 | 4.66 | 22000.0 | 1 |
| PC-3 CHEMBL390 | IC50 | 4.52 | 4.52 | 30000.0 | 1 |
| ATP-binding cassette sub-family C member 3 CHEMBL5918 | IC50 | 4.51 | 4.51 | 31000.0 | 1 |
| Trypanosoma cruzi CHEMBL368 | IC50 | 4.49 | 4.49 | 32610.0 | 1 |
| MCF7 CHEMBL387 | IC50 | 4.45 | 4.29 | 35400.0 | 2 |
| HT-29 CHEMBL384 | IC50 | 4.3 | 4.3 | 50000.0 | 1 |
| HCT-15 CHEMBL612263 | IC50 | 4.29 | 4.29 | 50900.0 | 1 |
| Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335 | IC50 | 4.26 | 4.26 | 55000.0 | 1 |
| Trypanosoma brucei rhodesiense CHEMBL612348 | IC50 | 4.23 | 4.23 | 59340.0 | 1 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | IC50 | 4.21 | 4.21 | 61000.0 | 1 |
| Indoleamine 2,3-dioxygenase 1 CHEMBL1075294 | IC50 | 4.21 | 4.21 | 61000.0 | 1 |
| LoVo CHEMBL614721 | IC50 | 4.19 | 4.19 | 65000.0 | 1 |
| MDA-MB-453 CHEMBL614334 | IC50 | 4.17 | 4.17 | 67100.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 25940.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 27400.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 5090.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 5680.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 25.94 | u-1 hr-1 ml-1 | Rattus norvegicus |
| AUC | 27.4 | u-1 hr-1 ml-1 | Rattus norvegicus |
| AUC | 25940.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 27400.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 9952.54 | ng.hr.mL-1 | Homo sapiens |
| CL | 9.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 3.5 | mL.min-1.kg-1 | Homo sapiens |
| CL | 6.6 | mL.min-1.kg-1 | Canis lupus familiaris |
| CL | 8.3 | mL.min-1.kg-1 | Macaca |
| CL | 22.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 28.18 | uL.min-1.(10^6cells)-1 | Homo sapiens |
| CL | 48.98 | mL.min-1.g-1 | Homo sapiens |
| CL | 150.0 | uL.min-1.(10^6cells)-1 | Rattus norvegicus |
| Cmax | 12388.18 | nM | Rattus norvegicus |
| Cmax | 0.77 | μg/mL | Rattus norvegicus |
| Cmax | 12388.18 | nM | Rattus norvegicus |
| Cmax | 12388.18 | nM | Rattus norvegicus |
| Cmax | 6300.0 | nM | Homo sapiens |
| Cmax | 6387.0 | nM | Homo sapiens |
| T1/2 | 4.01 | hr | Rattus norvegicus |
| T1/2 | 3.9 | hr | Rattus norvegicus |
| T1/2 | 4.01 | hr | Rattus norvegicus |
| T1/2 | 4.01 | hr | Rattus norvegicus |
| Tmax | 2.25 | hr | Rattus norvegicus |
| Tmax | 2.0 | hr | Rattus norvegicus |
| Tmax | 2.25 | hr | Rattus norvegicus |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine