Compound Detail

CHEMBL7002

CIGLITAZONE

🧪 Phase II

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🧪 Phase II

CC1(COc2ccc(CC3SC(=O)NC3=O)cc2)CCCCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL7002
Name	CIGLITAZONE
Phase	Phase II
Structure Type	MOL
InChI Key	YZFWTZACSRHJQD-UHFFFAOYSA-N

Known Names

ADD-3878 Ciglitazona Ciglitazone U-63,287 U-63287

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

333.4

MW (Da)

3.93

ALogP

HBA

HBD

55.4

PSA (Å²)

0.89

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Racemic

Flags

Natural Product

USAN Stem	-glitazone
USAN Year	1983

Extended Properties

Molecular Formula	C18H23NO3S
MW	333.45
Aromatic Rings	1
Heavy Atoms	23
NP-Likeness	0.29

Activity Summary

IC50 29 meas. best 7.07

Ki 16 meas. best 5.76

EC50 7 meas. best 5.52

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 2 CHEMBL205	IC50	7.07	7.07	86.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	6.65	6.65	225.0	2
Adenosine receptor A3 CHEMBL256	Ki	5.76	5.76	1722.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.66	5.66	2201.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.65	5.65	2220.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	5.64	5.64	2263.0	1
15-hydroxyprostaglandin dehydrogenase [NAD(+)] CHEMBL1293255	IC50	5.57	5.57	2700.0	2
Adenosine receptor A3 CHEMBL256	IC50	5.52	5.52	3047.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	5.52	4.9967	3000.0	3
Peroxisome proliferator-activated receptor gamma CHEMBL2459	EC50	5.52	5.52	3000.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Ki	5.51	5.51	3090.3	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	5.5	5.5	3168.0	1
Progesterone receptor CHEMBL1909044	Ki	5.42	5.42	3798.0	1
Substance-K receptor CHEMBL2327	Ki	5.38	5.38	4192.0	1
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	5.35	5.0667	4500.0	3
Epidermal growth factor receptor CHEMBL203	IC50	5.33	5.33	4655.0	1
Hepatitis B virus CHEMBL613497	IC50	5.3	5.3	5000.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.22	5.22	6053.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.21	5.21	6207.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	5.12	5.12	7505.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	5.1	5.1	7941.0	1
D(3) dopamine receptor CHEMBL234	Ki	5.04	5.04	9069.0	1
Delta-type opioid receptor CHEMBL236	Ki	5.02	5.02	9481.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	5.0	5.0	9893.0	1
Substance-K receptor CHEMBL2327	IC50	4.9	4.9	12576.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	4.88	4.88	13258.0	1
Beta-3 adrenergic receptor CHEMBL246	Ki	4.87	4.87	13403.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	4.83	4.83	14948.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	4.83	4.83	14947.0	1
Acetylcholinesterase CHEMBL220	IC50	4.82	4.82	15026.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	4.79	4.79	16224.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	4.78	4.78	16551.0	1
Beta-3 adrenergic receptor CHEMBL246	IC50	4.75	4.75	17871.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	4.7	4.7	19785.0	1
PC-12 CHEMBL612556	IC50	4.7	4.7	20000.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	4.68	4.68	21107.0	1
Delta-type opioid receptor CHEMBL236	IC50	4.57	4.57	26894.0	1
D(3) dopamine receptor CHEMBL234	IC50	4.57	4.57	26704.0	1
Melanocortin receptor 5 CHEMBL4608	Ki	4.57	4.57	26848.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	4.54	4.54	29193.0	1
Progesterone receptor CHEMBL1909044	IC50	4.54	4.54	29118.0	1
Melanocortin receptor 5 CHEMBL4608	IC50	4.54	4.54	28621.0	1
Bile salt export pump CHEMBL6020	IC50	4.42	4.42	37800.0	2
LNCaP CHEMBL612518	IC50	4.22	4.22	60000.0	1
Unchecked CHEMBL612545	IC50	4.11	4.11	78000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 2	IC50	=	86.0	nM	7.07	DRUGMATRIX: Carbonic Anhydrase II enzyme inhibition (substrate: 4-Nitrophenyl ac...	-
Amine oxidase [flavin-containing] B	IC50	=	225.0	nM	6.65	Inhibition of human recombinant MAO-B after 15 mins	20650633
Amine oxidase [flavin-containing] B	IC50	=	225.0	nM	6.65	Inhibition of recombinant human MAO-B	36162779
Adenosine receptor A3	Ki	=	1722.0	nM	5.76	DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA)	-
Sodium-dependent noradrenaline transporter	Ki	=	2201.0	nM	5.66	DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5...	-
Sodium-dependent noradrenaline transporter	IC50	=	2220.0	nM	5.65	DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5...	-
Muscarinic acetylcholine receptor M4	Ki	=	2263.0	nM	5.64	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
15-hydroxyprostaglandin dehydrogenase [NAD(+)]	IC50	=	2700.0	nM	5.57	Antagonist activity at 15-PGDH (unknown origin)	28231521
15-hydroxyprostaglandin dehydrogenase [NAD(+)]	IC50	=	2700.0	nM	5.57	Inhibition of PGDH (unknown origin)	24360556
Peroxisome proliferator-activated receptor gamma	EC50	=	3000.0	nM	5.52	Transactivation activity at Homo sapiens (human) PPARgamma	-
Adenosine receptor A3	IC50	=	3047.0	nM	5.52	DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA)	-
Peroxisome proliferator-activated receptor gamma	EC50	=	3000.0	nM	5.52	In vitro transcriptional activation of Peroxisome proliferator activated recepto...	8576907
Peroxisome proliferator-activated receptor gamma	Ki	=	3090.3	nM	5.51	In vitro binding to peroxisome proliferator activated receptor gamma (PPAR gamma...	9836620
Muscarinic acetylcholine receptor M3	Ki	=	3168.0	nM	5.5	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Progesterone receptor	Ki	=	3798.0	nM	5.42	DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020)	-
Substance-K receptor	Ki	=	4192.0	nM	5.38	DRUGMATRIX: Tachykinin NK2 radioligand binding (ligand: [3H] SR-48968)	-
Nuclear receptor subfamily 1 group I member 2	EC50	=	4500.0	nM	5.35	Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay	20966043
Epidermal growth factor receptor	IC50	=	4655.0	nM	5.33	DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: ...	-
Hepatitis B virus	IC50	=	5000.0	nM	5.3	Antiviral activity against HBV infected in human HepG2-hNTCP cells assessed as r...	36111355
Alpha-2B adrenergic receptor	Ki	=	6053.0	nM	5.22	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-

Literature References

PubMed	DOI	Target Context	# Activities
2642552	10.1021/jm00121a003	Mus musculus	8
20966043	10.1124/dmd.110.035105	Nuclear receptor subfamily 1 group I member 2	7
9544208	10.1021/jm9706168	Mus musculus	4
2913302	10.1021/jm00122a022	Mus musculus	4
1992133	10.1021/jm00105a050	Unchecked	3
1469692	10.1021/jm00102a016	Rattus norvegicus	3
2329563	10.1021/jm00167a022	Mus musculus	3
15109648	10.1016/j.bmcl.2004.02.087	PC-12	3
7966158	10.1021/jm00049a017	Mus musculus	2
1469692	10.1021/jm00102a016	Aldo-keto reductase family 1 member B1	2
10464006	10.1021/jm990260v	Mus musculus	2
7861410	10.1021/jm00004a008	No relevant target	2
11975517	10.1021/np010440j	Peroxisome proliferator-activated receptor gamma	2
1635060	10.1021/jm00092a012	Mus musculus	2
2329563	10.1021/jm00167a022	Rattus norvegicus	2
1560432	10.1021/jm00085a002	Mus musculus	2
18335975	10.1021/jm701212m	LNCaP	2
9836620	10.1021/jm9804127	Peroxisome proliferator-activated receptor gamma	2
1992133	10.1021/jm00105a050	Mus musculus	2
1992133	10.1021/jm00105a050	3T3-L1	2

Data from ChEMBL 36 via Core Engine