Compound Detail

CHEMBL231616

TRIAPINE

🧪 Phase III

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🧪 Phase III

NC(=S)N/N=C/c1ncccc1N

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL231616
Name	TRIAPINE
Phase	Phase III
Structure Type	MOL
InChI Key	XMYKNCNAZKMVQN-NYYWCZLTSA-N

Known Names

3-AP NSC-663249 Ocx 191 OCX-0191 OCX-191 PAN-811 Triapine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

195.2

MW (Da)

-0.17

ALogP

HBA

HBD

89.3

PSA (Å²)

0.35

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem

-pine

Extended Properties

Molecular Formula	C7H9N5S
MW	195.25
Aromatic Rings	1
Heavy Atoms	13
NP-Likeness	-1.80

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Ribonucleotide reductase inhibitor	INHIBITOR	Ribonucleotide reductase	✓	✓

Indications

Breast Neoplasms Breast Neoplasms, Male Carcinoma, Non-Small-Cell Lung Gallbladder Neoplasms Kidney Neoplasms Lung Neoplasms Neuroendocrine Tumors Pancreatic Neoplasms Prostatic Neoplasms, Castration-Resistant Endocrine Gland Neoplasms Neoplasms

Activity Summary

IC50 39 meas. best 6.73

Ki 1 meas. best 6.41

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Ribonucleoside-diphosphate reductase subunit M2 CHEMBL1954	IC50	6.73	6.73	185.0	1
SK-N-MC CHEMBL614163	IC50	6.58	6.485	260.0	4
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	Ki	6.41	6.41	388.0	1
PC-3 CHEMBL390	IC50	6.25	6.25	560.0	2
ADMET CHEMBL612558	IC50	6.18	6.18	660.0	1
A2780 CHEMBL614004	IC50	6.16	6.16	700.0	1
SW480 CHEMBL612544	IC50	6.08	6.08	840.0	1
MV4-11 CHEMBL613835	IC50	6.01	6.01	967.6	1
Ribonucleotide reductase CHEMBL3301398	IC50	5.92	5.92	1200.0	1
HCT-116 CHEMBL394	IC50	5.91	5.91	1226.0	1
L1210 CHEMBL386	IC50	5.89	5.89	1300.0	1
MES-SA CHEMBL614343	IC50	5.88	5.88	1305.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.85	5.54	1400.0	4
Unchecked CHEMBL612545	IC50	5.65	5.325	2250.0	4
A549 CHEMBL392	IC50	5.64	5.64	2288.0	1
MES-SA/Dx5 CHEMBL613827	IC50	5.6	5.6	2523.0	1
EC9706 CHEMBL4296412	IC50	5.51	5.51	3084.0	1
BGC-823 CHEMBL614526	IC50	5.51	5.51	3070.0	1
KB 3-1 CHEMBL614590	IC50	5.51	5.51	3100.0	1
HUVEC CHEMBL613979	IC50	5.46	5.46	3448.0	1
GES1 CHEMBL4296415	IC50	5.27	5.2433	5400.0	3
MGC-803 CHEMBL3706566	IC50	5.27	5.14	5411.0	2
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	IC50	5.04	5.04	9078.0	1
HGC-27 CHEMBL1075463	IC50	4.94	4.94	11495.0	1
SGC-7901 CHEMBL614909	IC50	4.74	4.74	18349.0	1
MCF7 CHEMBL387	IC50	4.72	4.72	18850.0	1
SMMC-7721 CHEMBL613831	IC50	4.37	4.37	42810.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1193.17	ng.hr.mL-1	Canis lupus familiaris
CL	40.62	mL.min-1.kg-1	Canis lupus familiaris
CL	518.1	mL.min-1.kg-1	Mus musculus
T1/2	0.175	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Ribonucleoside-diphosphate reductase subunit M2	IC50	=	185.0	nM	6.73	Inhibition of human RRM2 expressed in Escherichia coli BL21-codon plus(DE3) usin...	29253340
SK-N-MC	IC50	=	260.0	nM	6.58	Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay	17602603
SK-N-MC	IC50	=	260.0	nM	6.58	Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay	19601577
SK-N-MC	IC50	=	310.0	nM	6.51	Antiproliferative activity against human SK-N-MC cells by MTT assay	17142046
CDGSH iron-sulfur domain-containing protein 1	Ki	=	388.0	nM	6.41	Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M...	27687671
SK-N-MC	IC50	=	540.0	nM	6.27	Antiproliferative activity against human SK-N-MC cells by MTT assay	17963372
PC-3	IC50	=	560.0	nM	6.25	Antiproliferative activity against human PC-3 cells assessed as inhibition of ce...	33153765
PC-3	IC50	=	560.0	nM	6.25	Antiproliferative activity against human PC3 cells assessed as reduction in cell...	31614257
ADMET	IC50	=	660.0	nM	6.18	Antiproliferative activity against human SK-MN-C cells by MTT assay	18159922
A2780	IC50	=	700.0	nM	6.16	Cytotoxicity against human A2780 cells incubated for 72 hrs by MTT assay	27336684
SW480	IC50	=	840.0	nM	6.08	Cytotoxicity against human SW480 cells incubated for 72 hrs by MTT assay	27336684
MV4-11	IC50	=	967.6	nM	6.01	Antiproliferative activity against human MV4-11 cells assessed as reduction in c...	30835473
Ribonucleotide reductase	IC50	=	1200.0	nM	5.92	holoenzyme assay: A diverse compound library from NCI Developmental Therapeutics...	-
HCT-116	IC50	=	1226.0	nM	5.91	Dark cytotoxicity against human HCT116 cells expressing wild type p53 after 96 h...	24900837
L1210	IC50	=	1300.0	nM	5.89	Growth inhibition of mouse L1210 cells by MTS assay	30904782
MES-SA	IC50	=	1305.0	nM	5.88	Cytotoxicity against human MES-SA cells transfected with mCherry fluorescent pro...	27161177
NON-PROTEIN TARGET	IC50	=	1412.54	nM	5.85	Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay	19397322
NON-PROTEIN TARGET	IC50	=	1400.0	nM	5.85	Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay	19397322
Unchecked	IC50	=	2250.0	nM	5.65	Inhibition of human recombinant ribonucleotide reductase expressed in BL21 (DE3)...	18976907
A549	IC50	=	2288.0	nM	5.64	Antiproliferative activity against human A549 cells assessed as reduction in cel...	32438199

Literature References

PubMed	DOI	Target Context	# Activities
1433178	10.1021/jm00098a012	Mus musculus	19
30835473	10.1021/acs.jmedchem.8b01996	Unchecked	6
30835473	10.1021/acs.jmedchem.8b01996	MV4-11	5
27524608	10.1021/acs.jmedchem.6b01050	NON-PROTEIN TARGET	4
24900837	10.1021/ml400422a	HCT-116	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
27336684	10.1021/acs.jmedchem.6b00342	SW480	4
19397322	10.1021/jm800861c	NON-PROTEIN TARGET	4
31614257	10.1016/j.ejmech.2019.111764	Unchecked	3
30835473	10.1021/acs.jmedchem.8b01996	No relevant target	3
27524608	10.1021/acs.jmedchem.6b01050	KB-V1	2
27687671	10.1016/j.bmcl.2016.09.009	CDGSH iron-sulfur domain-containing protein 1	2
23276209	10.1021/jm301691s	ADMET	2
23276209	10.1021/jm301691s	SK-N-MC	2
27336684	10.1021/acs.jmedchem.6b00342	A2780	2
27161177	10.1016/j.ejmech.2016.03.078	MES-SA/Dx5	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
27336684	10.1021/acs.jmedchem.6b00342	Unchecked	2
9873695	10.1016/s0960-894x(98)00573-3	Canis familiaris	2
-	10.6019/CHEMBL4513161	Pseudomonas aeruginosa	2

Data from ChEMBL 36 via Core Engine