Compound Detail

CHEMBL595

PIOGLITAZONE

💊 Approved Drug

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

💊 Approved Drug

CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL595
Name	PIOGLITAZONE
Phase	Approved
Structure Type	MOL
InChI Key	HYAFETHFCAUJAY-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

AD-4833 Duetact Pioglitazona Pioglitazone U-72107 Zactos

Targets

121

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

356.4

MW (Da)

3.16

ALogP

HBA

HBD

68.3

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1999
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-glitazone
USAN Year	1989

Extended Properties

Molecular Formula	C19H20N2O3S
MW	356.45
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-0.47

Indications

Diabetes Mellitus Arthritis, Rheumatoid Atherosclerosis Coronary Disease Diabetes Mellitus, Type 2 Fatty Liver Friedreich Ataxia HIV Infections HIV-Associated Lipodystrophy Syndrome Hypercholesterolemia Hypertension Insulin Resistance Liver Diseases Metabolic Syndrome Non-alcoholic Fatty Liver Disease Non-alcoholic Fatty Liver Disease Adrenoleukodystrophy Adrenoleukodystrophy Alcoholism Alzheimer Disease

ATC Classification

A10BG03

pioglitazone

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: DRUGS USED IN DIABETES

Activity Summary

EC50 64 meas. best 7.06

IC50 39 meas. best 7.16

Ki 17 meas. best 7.21

Kd 1 meas. best 6.06

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Peroxisome proliferator-activated receptor gamma CHEMBL235	Ki	7.21	6.4709	62.0	11
MCF7 CHEMBL387	IC50	7.16	7.16	70.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	7.06	6.1929	88.0	48
Carbonic anhydrase 2 CHEMBL205	IC50	6.94	6.94	114.0	1
3T3-L1 CHEMBL614510	EC50	6.8	6.8	160.0	2
Amine oxidase [flavin-containing] B CHEMBL2039	Ki	6.7	6.5233	199.4	3
Bile salt export pump CHEMBL6020	IC50	6.58	6.48	260.0	6
K562 CHEMBL385	IC50	6.54	6.54	290.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	6.53	6.53	298.0	2
Unchecked CHEMBL612545	EC50	6.47	6.35	340.0	5
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	Ki	6.43	6.43	370.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL2459	EC50	6.26	6.21	550.0	2
Peroxisome proliferator-activated receptor gamma CHEMBL2459	IC50	6.16	6.16	700.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL4797	IC50	6.16	6.16	700.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	IC50	6.14	5.59	720.0	8
Mesenchymal stem cells CHEMBL5058627	EC50	6.1	6.0	790.0	3
Peroxisome proliferator-activated receptor gamma CHEMBL235	Kd	6.06	6.06	871.0	1
CDGSH iron-sulfur domain-containing protein 1 CHEMBL3308979	IC50	6.0	6.0	1000.0	1
Peroxisome proliferator-activated receptor alpha CHEMBL2128	IC50	5.94	5.94	1150.0	1
Unchecked CHEMBL612545	IC50	5.92	4.99	1200.0	2
Bile salt export pump CHEMBL2073674	IC50	5.7	5.7	2000.0	1
Amine oxidase [flavin-containing] B CHEMBL2993	Ki	5.68	5.68	2100.0	1
CDGSH iron-sulfur domain-containing protein 2 CHEMBL4523399	IC50	5.32	5.32	4800.0	1
Peroxisome proliferator-activated receptor alpha CHEMBL239	EC50	5.17	5.17	6680.0	3
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	IC50	5.06	5.06	8650.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	4.88	4.88	13200.0	1
THP-1 CHEMBL614245	IC50	4.73	4.725	18600.0	2
Unchecked CHEMBL612545	Ki	4.66	4.66	22055.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	4.46	4.46	35069.0	1
HT-29 CHEMBL384	IC50	4.39	4.39	40300.0	1
No relevant target CHEMBL2362975	IC50	4.36	4.36	44100.0	1
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.3	4.3	49500.0	1
Enoyl-[acyl-carrier-protein] reductase [NADH] CHEMBL2150835	IC50	4.1	4.1	79000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1753075.0	ng min	-
AUC	73072.25	ng.hr.mL-1	Mus musculus
AUC	64161.0	ng.hr.mL-1	Mus musculus
AUC	7998.74	ng.hr.mL-1	Homo sapiens
AUC	272.2	-	Chlorocebus sabaeus
CL	1.4	mL.min-1.kg-1	-
CL	3.6e-05	mL.min-1.g-1	Homo sapiens
CL	0.036	uL/min	Homo sapiens
Cmax	13087.39	nM	-
Cmax	2946.0	nM	Homo sapiens
F	112.0	%	Eutheria
T1/2	3.8	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Peroxisome proliferator-activated receptor gamma	Ki	=	62.0	nM	7.21	Binding affinity to PPARgamma (unknown origin) by TR-FRET assay	30672698
MCF7	IC50	=	70.0	nM	7.16	Anticancer activity against human MCF7 cells assessed as cell growth inhibition ...	36481599
Peroxisome proliferator-activated receptor gamma	EC50	=	88.0	nM	7.06	Agonist activity at PPARgamma assessed as transcriptional activation	20219371
Peroxisome proliferator-activated receptor gamma	Ki	=	96.0	nM	7.02	Binding affinity to PPAR-gamma (unknown origin) by TR-FRET assay	33325691
Peroxisome proliferator-activated receptor gamma	EC50	=	98.0	nM	7.01	Transactivation of GAL4-DBD fused human PPARgamma ligand binding domain expresse...	30429097
Peroxisome proliferator-activated receptor gamma	EC50	=	100.0	nM	7.0	Transactivation of human full length PPARgamma expressed in HEK293 cells after 1...	30362739
Carbonic anhydrase 2	IC50	=	114.0	nM	6.94	DRUGMATRIX: Carbonic Anhydrase II enzyme inhibition (substrate: 4-Nitrophenyl ac...	-
Peroxisome proliferator-activated receptor gamma	EC50	=	140.0	nM	6.85	Activation of Gal4-tagged human PPARgamma expressed in CHO cells by luciferase r...	20656494
Peroxisome proliferator-activated receptor gamma	Ki	=	150.0	nM	6.82	Binding affinity to PPARgamma (unknown origin) assessed as inhibition constant b...	36967575
3T3-L1	EC50	=	160.0	nM	6.8	Effective concentration for 50% enhancement of insulin-induced triglyceride accu...	9599241
3T3-L1	EC50	=	160.0	nM	6.8	Effective concentration for 50% enhancement of insulin-induced triglyceride accu...	9599241
Peroxisome proliferator-activated receptor gamma	EC50	=	200.0	nM	6.7	Transactivation of GAL4-fused human PPARgamma ligand binding domain transfected ...	23130964
Peroxisome proliferator-activated receptor gamma	EC50	=	200.0	nM	6.7	Transactivation of human PPARgamma expressed in African green monkey COS7 cells ...	26595749
Peroxisome proliferator-activated receptor gamma	EC50	=	200.0	nM	6.7	Agonist activity at PPARgamma in human BMMSC cells assessed as promotion of adip...	36529937
Amine oxidase [flavin-containing] B	Ki	=	199.4	nM	6.7	Inhibition of human recombinant soluble MAO-B expressed in Pichia pastoris incub...	25600407
Peroxisome proliferator-activated receptor gamma	EC50	=	210.0	nM	6.68	Agonist activity at human PPARgamma expressed in HEK293 cells incubated for 18 h...	25333853
Peroxisome proliferator-activated receptor gamma	EC50	=	240.0	nM	6.62	Agonist activity at PPARgamma in human HepG2 cells assessed as activation of PPR...	30001846
Peroxisome proliferator-activated receptor gamma	EC50	=	250.0	nM	6.6	Transactivation of full length human PPARgamma2 expressed in HEK293T cells co-ex...	30676741
Bile salt export pump	IC50	=	260.0	nM	6.58	Inhibition of human BSEP expressed in HEK293 cell membrane vesicles assessed as ...	32511920
Bile salt export pump	IC50	=	262.1	nM	6.58	Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21...	22961681

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	512
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
38460271	10.1016/j.ejmech.2024.116279	Rattus norvegicus	13
38252989	10.1016/j.ejmech.2024.116139	Rattus norvegicus	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
-	10.1039/C3MD00138E	Mus musculus	10
37793328	10.1016/j.ejmech.2023.115826	Mus musculus	10
30676741	10.1021/acs.jmedchem.8b01573	Peroxisome proliferator-activated receptor gamma	9
38865743	10.1016/j.ejmech.2024.116567	Mus musculus	9
22575535	10.1016/j.ejmech.2012.04.015	Rattus norvegicus	8
29031063	10.1016/j.ejmech.2017.09.071	SCC-15	8
23391145	10.1021/jm400033f	Mus musculus	8
14584939	10.1021/jm0309046	Mus musculus	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
30108748	10.1039/C6MD00467A	Mus musculus	8
14643306	10.1016/j.bmcl.2003.09.052	Mus musculus	8
29525431	10.1016/j.ejmech.2018.02.069	Mus musculus	7
10098657	10.1016/s0960-894x(99)00039-6	Mus musculus	7
11831892	10.1021/jm010964g	Mus musculus	7
11831892	10.1021/jm010964g	ADMET	7

Data from ChEMBL 36 via Core Engine