Compound Detail

CHEMBL727

THIOGUANINE

💊 Approved Drug

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💊 Approved Drug

Nc1nc2[nH]cnc2c(=S)[nH]1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL727
Name	THIOGUANINE
Phase	Approved
Structure Type	MOL
InChI Key	WYWHKKSPHMUBEB-UHFFFAOYSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL1812063

Known Names

Lanvis NSC-752 NSC-76504 Tabloid Thioguanine Thioguanine anhydrous Thioguanine hemihydrate Thioguanine, anhydrous Tioguanina Tioguanine Tioguanine hemihydrate

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

167.2

MW (Da)

0.60

ALogP

HBA

HBD

83.4

PSA (Å²)

0.50

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1966
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product Prodrug

USAN Year

1965

Extended Properties

Molecular Formula	C5H5N5S
MW	167.20
Aromatic Rings	2
Heavy Atoms	11
NP-Likeness	-0.18

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor	INHIBITOR	Inosine-5'-monophosphate dehydrogenase (IMPDH)	✓	✓
DNA inhibitor	INHIBITOR	DNA	✓	✓

Indications

Neoplasms Anemia, Refractory Anemia, Refractory, with Excess of Blasts Brain Neoplasms Brain Neoplasms Central Nervous System Neoplasms Leukemia Leukemia, Basophilic, Acute Leukemia, Biphenotypic, Acute Leukemia, Erythroblastic, Acute Leukemia, Lymphoid Leukemia, Megakaryoblastic, Acute Leukemia, Monocytic, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myelomonocytic, Acute Leukemia, Myelomonocytic, Chronic Lymphoma Myelodysplastic Syndromes Myeloproliferative Disorders

ATC Classification

L01BB03

tioguanine

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 45 meas. best 7.31

EC50 9 meas. best 6.57

Ki 2 meas. best 4.91

Kd 1 meas. best 4.75

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	7.31	5.966	49.3	15
Replicase polyprotein 1ab CHEMBL4523582	IC50	7.0	5.86	100.0	4
THP-1 CHEMBL614245	EC50	6.57	6.57	270.0	1
P388 CHEMBL389	IC50	6.52	6.52	300.0	1
Unchecked CHEMBL612545	EC50	6.5	6.5	320.0	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.22	6.22	601.0	1
K562 CHEMBL385	EC50	6.13	6.13	740.0	1
CCRF-CEM CHEMBL382	EC50	6.06	6.06	870.1	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.03	5.735	941.6	2
HT-29 CHEMBL384	IC50	5.91	5.91	1240.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.89	5.4988	1280.0	8
K562 CHEMBL385	IC50	5.81	5.61	1540.0	2
SARS-CoV-2 CHEMBL4303835	IC50	5.77	5.77	1710.0	1
Bacillus anthracis CHEMBL613904	IC50	5.7	5.7	2000.0	1
SARS-CoV-2 CHEMBL4303835	EC50	5.67	5.67	2130.0	1
A549 CHEMBL392	IC50	5.55	5.55	2820.0	1
CCRF-CEM CHEMBL382	IC50	5.53	5.53	2980.0	1
HEK-293T CHEMBL3706568	EC50	5.44	5.44	3600.0	1
HL-60 CHEMBL383	EC50	5.41	5.41	3897.0	1
DAN-G CHEMBL614033	IC50	5.37	5.37	4320.0	1
Mitogen-activated protein kinase 3 CHEMBL3385	IC50	5.26	5.26	5516.0	1
Plasmodium falciparum CHEMBL364	IC50	5.0	4.835	10000.0	2
Adenosine receptor A3 CHEMBL256	Ki	4.91	4.91	12258.0	1
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358	IC50	4.79	4.79	16159.0	1
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase CHEMBL3217379	Kd	4.75	4.75	18000.0	1
Adenosine receptor A3 CHEMBL256	IC50	4.66	4.66	21687.0	1
Ubiquitin carboxyl-terminal hydrolase 2 CHEMBL1293227	IC50	4.38	4.38	42000.0	1
Tyrosinase CHEMBL3318	Ki	4.28	4.28	52000.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	4.03	4.03	92420.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	49.27	nM	7.31	PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
Replicase polyprotein 1ab	IC50	=	100.0	nM	7.0	Inhibition of SARS-CoV-2 papain-like protease-mediated de-ISGylation	35620927
Unchecked	IC50	=	108.05	nM	6.97	PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
Unchecked	IC50	=	138.55	nM	6.86	PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c...	-
Unchecked	IC50	=	163.26	nM	6.79	PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (...	-
THP-1	EC50	=	270.0	nM	6.57	Antiproliferative activity against human THP-1 cells with low HGPRT expression i...	36374020
P388	IC50	=	300.0	nM	6.52	Antiproliferative activity against mouse P388 cells after 48 hrs by MTT assay	2778449
Unchecked	EC50	=	320.0	nM	6.5	PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP...	-
Unchecked	IC50	=	343.1	nM	6.46	PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf...	-
Unchecked	IC50	=	372.99	nM	6.43	PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ...	-
Unchecked	IC50	=	402.37	nM	6.39	PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
Replicase polyprotein 1ab	IC50	=	500.0	nM	6.3	Inhibition of TAP-tagged SARS-CoV-2 papain-like protease nsp123	35620927
Prostaglandin G/H synthase 1	IC50	=	601.0	nM	6.22	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Unchecked	IC50	=	622.4	nM	6.21	PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de...	-
K562	EC50	=	740.0	nM	6.13	Antiproliferative activity against human K562 cells with low HGPRT expression in...	36374020
CCRF-CEM	EC50	=	870.1	nM	6.06	Cytotoxicity against human CCRF-CEM cells after 48 hrs by cell titer-blue assay	19743858
NON-PROTEIN TARGET	EC50	=	941.6	nM	6.03	Cytotoxicity against human CCRF-CEM/C2 cells after 48 hrs by cell titer-blue ass...	19743858
Replicase polyprotein 1ab	IC50	=	1000.0	nM	6.0	Inhibition of TAP-tagged SARS-CoV-2 papain-like protease nsp23	35620927
HT-29	IC50	=	1240.0	nM	5.91	Antiproliferative activity against human HT-29 cells after 96 hrs by MTT assay	2778449
NON-PROTEIN TARGET	IC50	=	1280.0	nM	5.89	Cytotoxicity against human T3M4 cells by crystal violet staining	20930123

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	900
16472241	10.2174/1570163043334794	Hepatotoxicity	18
20605656	10.1016/j.ejmech.2010.05.003	CCRF-CEM	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
3761323	10.1021/jm00160a043	EMT6	8
20930123	10.1124/dmd.110.033613	NON-PROTEIN TARGET	7
7205884	10.1021/jm00134a008	L1210	7
17149876	10.1021/jm061012j	Unchecked	6
2778449	10.1021/np50063a010	HT-29	5
35620927	10.1021/acs.jmedchem.2c00303	Replicase polyprotein 1ab	4
2778449	10.1021/np50063a010	P388	4
2738881	10.1021/jm00127a013	Rattus norvegicus	3
27391135	10.1016/j.ejmech.2016.06.034	NON-PROTEIN TARGET	3
20921305	10.1128/aac.01029-10	Bacillus anthracis	3
7205884	10.1021/jm00134a008	NON-PROTEIN TARGET	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
7205884	10.1021/jm00134a008	Mus musculus	3
17145120	10.1016/j.ejmech.2006.10.012	NCI-H226	2

Data from ChEMBL 36 via Core Engine