Compound Detail

CHEMBL7492

PIRITREXIM

🧪 Phase II

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🧪 Phase II

COc1ccc(OC)c(Cc2cnc3nc(N)nc(N)c3c2C)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL7492
Name	PIRITREXIM
Phase	Phase II
Structure Type	MOL
InChI Key	VJXSSYDSOJBUAV-UHFFFAOYSA-N

Known Names

Bw 301u Bw-301u Piritrexim Piritrexima Piritrexime TCMDC-137235

Targets

132

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

325.4

MW (Da)

2.11

ALogP

HBA

HBD

109.2

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Year

1986

Extended Properties

Molecular Formula	C17H19N5O2
MW	325.37
Aromatic Rings	3
Heavy Atoms	24
NP-Likeness	-0.23

Mechanism of Action

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

Indications

Urethral Neoplasms Urinary Bladder Neoplasms

Activity Summary

IC50 127 meas. best 9.21

Ki 5 meas. best 10.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dihydrofolate reductase CHEMBL202	Ki	10.6	8.5	0.0	3
Dihydrofolate reductase CHEMBL1926	Ki	9.85	9.85	0.1	1
Unchecked CHEMBL612545	IC50	9.21	8.31	0.6	6
Dihydrofolate reductase CHEMBL5457	IC50	9.21	9.21	0.6	5
Dihydrofolate reductase CHEMBL2363	IC50	9.0	8.6716	1.0	31
Dihydrofolate reductase CHEMBL2902	IC50	8.82	8.82	1.5	1
Dihydrofolate reductase CHEMBL2329	Ki	8.72	8.72	1.9	1
Dihydrofolate reductase CHEMBL202	IC50	8.7	8.628	2.0	5
Bifunctional dihydrofolate reductase-thymidylate synthase CHEMBL2425	IC50	8.37	7.8918	4.3	28
Dihydrofolate reductase CHEMBL1809	IC50	7.96	7.7125	11.0	4
Dihydrofolate reductase CHEMBL1926	IC50	7.89	7.576	13.0	30
Toxoplasma gondii CHEMBL612888	IC50	7.7	7.7	20.0	1
P388 CHEMBL389	IC50	7.68	7.68	21.0	1
A549 CHEMBL392	IC50	7.62	7.62	24.0	1
Vero CHEMBL391	IC50	7.52	7.52	30.0	1
Dihydrofolate reductase CHEMBL2576	IC50	7.51	7.51	31.0	1
Dihydrofolate reductase CHEMBL2364669	IC50	7.51	7.51	31.0	1
Dihydrofolate reductase CHEMBL2329	IC50	7.4	7.4	40.0	1
Dihydrofolate reductase CHEMBL2057	IC50	7.39	7.39	41.0	1
U-87 MG CHEMBL614247	IC50	7.32	7.32	48.0	1
U373 MG CHEMBL615024	IC50	7.26	7.26	55.0	1
HCT-8 CHEMBL613510	IC50	7.17	7.17	68.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.16	7.14	70.0	2
D54 cell line CHEMBL612247	IC50	6.64	6.64	230.0	1
NCI-H460 CHEMBL396	IC50	6.58	6.58	260.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dihydrofolate reductase	Ki	=	0.025	nM	10.6	Inhibition of human recombinant Dihydrofolate reductase enzyme	8632413
Dihydrofolate reductase	Ki	=	0.143	nM	9.85	Binding affinity was reported with purified recombinant Pneumocystis carinii Dih...	7490723
Dihydrofolate reductase	IC50	=	0.61	nM	9.21	Inhibitory concentration against Mycobacterium avium dihydrofolate reductase	15026078
Dihydrofolate reductase	IC50	=	0.61	nM	9.21	Concentration required to inhibit the Mycobacterium avium Dihydrofolate reductas...	15115391
Dihydrofolate reductase	IC50	=	0.61	nM	9.21	Inhibition of Dihydrohydrofolate reductase(DHFR) of Mycobacterium avium	12699390
Dihydrofolate reductase	IC50	=	0.61	nM	9.21	Inhibitory concentration against Mycobacterium avium DHFR	15974594
Unchecked	IC50	=	0.61	nM	9.21	Inhibition of Mycobacterium avium DHFR	23627352
Dihydrofolate reductase	IC50	=	0.61	nM	9.21	Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium	14998335
Dihydrofolate reductase	IC50	=	1.0	nM	9.0	Inhibition against Dihydrofolate reductase in rat liver	9089339
Dihydrofolate reductase	IC50	=	1.0	nM	9.0	Inhibition of rat liver Dihydrofolate reductase	7783147
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Concentration inhibiting rat liver dihydrofolate reductase.	7629801
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibitory activity against rat DHFR*	12699390
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibition of Dihydrofolate reductase (DHFR) of in rat liver	7799402
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibition of partially purified dihydrofolate reductase (DHFR) from rat liver	11754594
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibitory activity against dihydrofolate reductase (DHFR) from rat liver	9804692
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated...	9301666
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibition of Dihydrofolate Reductase of Rat Liver.	9046338
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibition of rat liver dihydrofolate reductase	8230134
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibitory concentration against Rat liver Dihydrofolate reductase	9191971
Dihydrofolate reductase	IC50	=	1.5	nM	8.82	Inhibitory concentration against rat liver dihydrofolate reductase (DHFR)	9301665

Literature References

PubMed	DOI	Target Context	# Activities
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
11754594	10.1021/jm010407u	Dihydrofolate reductase	6
14998335	10.1021/jm030438k	Dihydrofolate reductase	6
7877140	10.1021/jm00005a002	Dihydrofolate reductase	5
23627352	10.1021/jm400086g	Unchecked	5
8632413	10.1021/jm9505122	Mus musculus	5
12699390	10.1021/jm020466n	Dihydrofolate reductase	5
31176699	10.1016/j.bmcl.2019.06.004	Unchecked	4
20485427	10.1038/nature09107	Plasmodium falciparum	4
9301665	10.1021/jm970271t	Dihydrofolate reductase	4
7490723	10.1021/jm00024a001	Dihydrofolate reductase	4
8632413	10.1021/jm9505122	P388	4
15974594	10.1021/jm0581718	Dihydrofolate reductase	3
15115391	10.1021/jm030599o	Unchecked	3
14584957	10.1021/jm030312n	Dihydrofolate reductase	3
23627352	10.1021/jm400086g	Dihydrofolate reductase	3
15115391	10.1021/jm030599o	Dihydrofolate reductase	3
15026078	10.1016/j.bmcl.2003.12.103	Unchecked	3
20014752	10.1021/tx900326k	Hepatotoxicity	3

Data from ChEMBL 36 via Core Engine