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Compound Detail

CHEMBL843

ROSIGLITAZONE MALEATE
💊 Approved Drug
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💊 Approved Drug
CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1.O=C(O)/C=C\C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL843
Name ROSIGLITAZONE MALEATE
Phase Approved
Structure Type MOL
InChI Key SUFUKZSWUHZXAV-BTJKTKAUSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL121
Active Moiety CHEMBL121

Known Names

Avandia BRL-49653-C BRL-49653C NSC-717764 Rosiglitazone maleate Rosiglitazone maleate component of avandamet Rosiglitazone maleate component of avandaryl Rosiglitzazone maleate
4
Targets
6
Activities
3
Assay Types
22
PK Parameters
20
Publications
8
Known Names
13
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Availability Withdrawn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

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn
USAN Stem -glitazone
USAN Year 1997

Extended Properties

Molecular Formula C22H23N3O7S
MW 473.51
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.93

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 Atherosclerosis Insulin Resistance Central Nervous System Neoplasms Head and Neck Neoplasms Heart Failure Leukoplakia, Oral Non-alcoholic Fatty Liver Disease Non-alcoholic Fatty Liver Disease Pituitary ACTH Hypersecretion Sarcoma HIV Infections

Drug Warnings

Withdrawn
cardiotoxicity
Increased risk of ischaemic heart disease
Country: Armenia; Guatemala; Egypt; New Zealand; Madagascar; European Union   Year: 2010
Withdrawn
cardiotoxicity
Increased risk of ischaemic heart disease
Country: Armenia; Guatemala; Egypt; New Zealand; Madagascar; European Union   Year: 2010
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

Ki 3 meas. best 7.85
Kd 2 meas. best 6.19
EC50 1 meas. best 6.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 Ki 7.85 7.36 14.0 2
RXR alpha/PPAR gamma
CHEMBL2111394
 Kd 6.19 6.19 650.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 EC50 6.14 6.14 730.0 1
Retinoic acid receptor gamma
CHEMBL2003
 Ki 5.0 5.0 10000.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
 Kd 4.82 4.82 15010.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 59200.0 ng.hr.mL-1 Rattus norvegicus
AUC 358.0 ng.hr.mL-1 Homo sapiens
AUC 733.0 ng.hr.mL-1 Homo sapiens
AUC 2971.0 ng.hr.mL-1 Homo sapiens
AUC 2890.0 ng.hr.mL-1 Homo sapiens
CL/F 3.03 L/hr Homo sapiens
CL/F 2.89 L/hr Homo sapiens
CL/F 2.85 L/hr Homo sapiens
CL/F 2.97 L/hr Homo sapiens
Cmax 82251.57 nM Rattus norvegicus
Cmax 212.62 nM Homo sapiens
Cmax 436.44 nM Homo sapiens
Cmax 1673.01 nM Homo sapiens
Cmax 1208.59 nM Homo sapiens
Excretion 23.0 % Homo sapiens
Excretion 64.0 % Homo sapiens
T1/2 1.02 hr Rattus norvegicus
T1/2 3.16 hr Homo sapiens
T1/2 3.15 hr Homo sapiens
T1/2 3.37 hr Homo sapiens
T1/2 3.59 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Peroxisome proliferator-activated receptor gamma Ki = 14.0 nM 7.85 Binding affinity towards human peroxisome proliferator activated receptor gamma ... 12951090
Peroxisome proliferator-activated receptor gamma Ki = 136.0 nM 6.87 Binding affinity towards peroxisome proliferator activated receptor gamma (PPAR ... 12951090
RXR alpha/PPAR gamma Kd = 650.0 nM 6.19 Binding affinity to human PPARgamma-LBD (206 to 477 residues)/human RXRalpha-LBD... 36923911
Peroxisome proliferator-activated receptor gamma EC50 = 730.0 nM 6.14 Peroxisome proliferator activated receptor gamma agonistic activity in HepG2 cel... 10714503
Retinoic acid receptor gamma Ki = 10000.0 nM 5.0 Binding affinity against Retinoic acid receptor gamma was determined in vitro by... 12801232
Retinoic acid receptor RXR-alpha Kd = 15010.0 nM 4.82 Binding affinity to RXRalpha-LBD (unknown origin) measured up to 120 sec by surf... 28089347

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1317
9572887 10.1021/jm970444e Rattus norvegicus 14
12951090 10.1016/s0960-894x(03)00702-9 Mus musculus 11
9572887 10.1021/jm970444e ADMET 6
12801232 10.1021/jm020340q Retinoic acid receptor RXR-alpha 5
28089347 10.1016/j.bmcl.2016.12.058 Retinoic acid receptor RXR-alpha 4
36923911 10.1021/acsmedchemlett.2c00509 RXR alpha/PPAR gamma 4
20627471 10.1016/j.ejmech.2010.05.020 Mus musculus 3
12801232 10.1021/jm020340q Mus musculus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
28089347 10.1016/j.bmcl.2016.12.058 Retinoic acid receptor gamma 2
12801232 10.1021/jm020340q Rattus norvegicus 2
12801232 10.1021/jm020340q RXR alpha/PPAR gamma 2
12951090 10.1016/s0960-894x(03)00702-9 Peroxisome proliferator-activated receptor gamma 2
12951090 10.1016/s0960-894x(03)00702-9 Peroxisome proliferator-activated receptor alpha 2
10714503 10.1016/s0960-894x(00)00003-2 Peroxisome proliferator-activated receptor gamma 1
10714503 10.1016/s0960-894x(00)00003-2 Mus musculus 1
12801232 10.1021/jm020340q Unchecked 1
28089347 10.1016/j.bmcl.2016.12.058 Nuclear receptor subfamily 4immunitygroup A member 1 1

Data from ChEMBL 36 via Core Engine