Compound Detail
CHEMBL121
ROSIGLITAZONE 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL121 |
| Name | ROSIGLITAZONE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | YASAKCUCGLMORW-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
34
Targets
316
Activities
4
Assay Types
30
PK Parameters
20
Publications
14
Known Names
20
Indications
1
Mechanisms
Molecular Properties
357.4
MW (Da)
2.49
ALogP
6
HBA
1
HBD
71.5
PSA (Ų)
0.82
QED
0
Ro5 Violations
7
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1999 |
| Availability | Withdrawn |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 Diabetes Mellitus, Type 2 Alzheimer Disease Atherosclerosis Cardiovascular Diseases Coronary Disease Diabetic Neuropathies Glucose Intolerance Glucose Intolerance Hypercholesterolemia Hypertension Lipid Metabolism Disorders Metabolic Diseases Metabolic Syndrome Multiple Organ Failure Prostatic Neoplasms Arthritis, Rheumatoid Asthma Cognitive Dysfunction Colitis, Ulcerative
ATC Classification
A10BG02
rosiglitazone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES
Drug Warnings
Withdrawn
cardiotoxicity
Increased cardiovascular risk outweighs its benefit; Cardiovascular risk; Elevated risk of cardiovascular events
Withdrawn
cardiotoxicity
Elevated risk of cardiovascular events
Activity Summary
EC50 198 meas. best 9.0
IC50 84 meas. best 8.11
Ki 25 meas. best 9.64
Kd 9 meas. best 8.92
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Type-1 angiotensin II receptor A CHEMBL329 | Ki | 9.64 | 9.64 | 0.2 | 1 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | EC50 | 9.0 | 7.0904 | 1.0 | 159 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | Kd | 8.92 | 6.9238 | 1.2 | 8 |
| Unchecked CHEMBL612545 | EC50 | 8.7 | 7.1717 | 2.0 | 6 |
| Peroxisome proliferator-activated receptor alpha CHEMBL239 | EC50 | 8.4 | 5.8489 | 4.0 | 18 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | Ki | 8.24 | 7.3858 | 5.8 | 19 |
| Peroxisome proliferator-activated receptor gamma CHEMBL235 | IC50 | 8.11 | 6.8938 | 7.7 | 47 |
| U2OS CHEMBL615023 | EC50 | 7.52 | 7.52 | 30.0 | 1 |
| Peroxisome proliferator-activated receptor gamma CHEMBL2459 | EC50 | 7.52 | 7.2867 | 30.0 | 3 |
| CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168 | Ki | 7.51 | 7.51 | 31.0 | 1 |
| Peroxisome proliferator-activated receptor alpha CHEMBL2128 | IC50 | 7.1 | 7.1 | 80.0 | 1 |
| 3T3-L1 CHEMBL614510 | EC50 | 6.92 | 6.34 | 120.0 | 2 |
| Unchecked CHEMBL612545 | IC50 | 6.9 | 5.9633 | 125.0 | 3 |
| Unchecked CHEMBL612545 | Kd | 6.43 | 6.43 | 370.0 | 1 |
| CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168 | IC50 | 6.14 | 6.14 | 731.0 | 1 |
| Amine oxidase [flavin-containing] B CHEMBL2039 | IC50 | 6.08 | 6.08 | 832.0 | 2 |
| HUVEC CHEMBL613979 | IC50 | 5.96 | 5.96 | 1100.0 | 1 |
| CDGSH iron-sulfur domain-containing protein 1 CHEMBL3308979 | IC50 | 5.96 | 5.96 | 1100.0 | 1 |
| Peroxisome proliferator-activated receptor CHEMBL3559683 | EC50 | 5.8 | 5.8 | 1600.0 | 1 |
| CDGSH iron-sulfur domain-containing protein 2 CHEMBL4523399 | IC50 | 5.64 | 5.64 | 2290.0 | 1 |
| Bile salt export pump CHEMBL6020 | IC50 | 5.55 | 5.3583 | 2800.0 | 6 |
| Thromboxane-A synthase CHEMBL1835 | IC50 | 5.45 | 5.45 | 3560.0 | 1 |
| Peroxisome proliferator-activated receptor delta CHEMBL3979 | EC50 | 5.44 | 5.2567 | 3620.0 | 3 |
| Carbonic anhydrase 2 CHEMBL205 | IC50 | 5.39 | 5.39 | 4069.0 | 1 |
| Amine oxidase [flavin-containing] B CHEMBL2039 | Ki | 5.38 | 5.38 | 4200.0 | 1 |
| L6 CHEMBL614793 | EC50 | 5.35 | 5.325 | 4490.0 | 2 |
| L6 CHEMBL614793 | IC50 | 5.32 | 5.32 | 4800.0 | 1 |
| Hepatic sodium/bile acid cotransporter CHEMBL5287 | IC50 | 5.29 | 5.29 | 5100.0 | 1 |
| Hepatitis B virus CHEMBL613497 | IC50 | 5.29 | 5.29 | 5100.0 | 1 |
| MDA-MB-231 CHEMBL400 | IC50 | 5.28 | 5.28 | 5230.0 | 1 |
| Amine oxidase [flavin-containing] B CHEMBL2993 | Ki | 5.24 | 5.24 | 5800.0 | 1 |
| Keratinocyte CHEMBL613995 | IC50 | 5.1 | 5.1 | 8000.0 | 1 |
| Free fatty acid receptor 1 CHEMBL4422 | EC50 | 4.94 | 4.94 | 11481.5 | 1 |
| DU-145 CHEMBL613508 | IC50 | 4.8 | 4.8 | 16000.0 | 1 |
| RAW264.7 CHEMBL612557 | IC50 | 4.76 | 4.76 | 17500.0 | 1 |
| PC-3 CHEMBL390 | IC50 | 4.69 | 4.69 | 20300.0 | 1 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | IC50 | 4.68 | 4.68 | 21000.0 | 1 |
| Amine oxidase [flavin-containing] A CHEMBL1951 | Ki | 4.56 | 4.56 | 27600.0 | 1 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | IC50 | 4.53 | 4.53 | 29500.0 | 1 |
| Amine oxidase [flavin-containing] A CHEMBL3358 | Ki | 4.49 | 4.49 | 32600.0 | 1 |
| Bile salt export pump CHEMBL2073674 | IC50 | 4.4 | 4.4 | 40000.0 | 1 |
| HT-29 CHEMBL384 | IC50 | 4.35 | 4.35 | 45000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 5862.02 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 5862.02 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 873922.0 | ng min | - |
| AUC | 14565.37 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 4080.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 113308.48 | ng.hr.mL-1 | Mus musculus |
| AUC | 574406.08 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 250208.0 | ng.hr.mL-1 | Mus musculus |
| AUC | 965088.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 19194.53 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 33670.85 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 207672.64 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 114380.8 | ng.hr.mL-1 | Mus musculus |
| AUC | 3216.96 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 21839.58 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 208637.73 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 2308347.52 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 5862.02 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 113308.48 | ng.hr.mL-1 | Mus musculus |
| AUC | 214464.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 78636.8 | ng.hr.mL-1 | Mus musculus |
| AUC | 2865.6 | ng.hr.mL-1 | Homo sapiens |
| AUC | 7.068 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | - | - | Rattus norvegicus |
| AUC | 6550.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 525000.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | - | - | Rattus norvegicus |
| CL | 2.7 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 2.7 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 2.1 | mL.min-1.kg-1 | - |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine