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Compound Detail

CHEMBL119

TRIMETREXATE
💊 Approved Drug
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💊 Approved Drug
COc1cc(NCc2ccc3nc(N)nc(N)c3c2C)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL119
Name TRIMETREXATE
Phase Approved
Structure Type MOL
InChI Key NOYPYLRCIDNJJB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

CI-898 NSC-249008 Trimetrexate Trimetrexato
30
Targets
182
Activities
2
Assay Types
5
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

369.4
MW (Da)
2.74
ALogP
8
HBA
3
HBD
117.5
PSA (Ų)
0.61
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Discontinued
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -trexate
USAN Year 1981

Extended Properties

Molecular Formula C19H23N5O3
MW 369.43
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.57

Indications

Amebiasis

ATC Classification

P01AX07
trimetrexate
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 173 meas. best 9.38
Ki 9 meas. best 10.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL202
 Ki 10.4 8.555 0.0 4
Dihydrofolate reductase
CHEMBL4564
 Ki 10.22 9.655 0.1 2
Dihydrofolate reductase
CHEMBL202
 IC50 9.38 8.2345 0.4 11
Dihydrofolate reductase
CHEMBL1926
 Ki 9.15 9.15 0.7 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 8.87 7.8588 1.4 34
Unchecked
CHEMBL612545
 IC50 8.87 8.5975 1.4 8
Dihydrofolate reductase
CHEMBL5457
 IC50 8.82 8.82 1.5 4
HCT-8
CHEMBL613510
 IC50 8.74 8.74 1.8 1
Dihydrofolate reductase
CHEMBL2329
 Ki 8.72 8.72 1.9 1
Plasmodium falciparum
CHEMBL364
 IC50 8.72 7.7117 1.9 6
P388
CHEMBL389
 IC50 8.57 8.57 2.7 1
Dihydrofolate reductase
CHEMBL2363
 IC50 8.52 8.4829 3.0 34
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.39 8.0429 4.1 7
A549
CHEMBL392
 IC50 8.28 8.28 5.3 1
SCC-7
CHEMBL614147
 IC50 8.2 8.2 6.3 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1163130
 Ki 8.18 8.18 6.6 1
R2
CHEMBL614385
 IC50 8.17 8.17 6.7 1
Dihydrofolate reductase
CHEMBL1809
 IC50 8.15 7.5229 7.0 7
SCC-25
CHEMBL614901
 IC50 8.1 8.1 8.0 1
IGROV-1
CHEMBL613984
 IC50 8.07 7.995 8.6 2
U373 MG
CHEMBL615024
 IC50 8.02 8.02 9.6 1
Dihydrofolate reductase
CHEMBL1926
 IC50 8.0 7.4025 10.0 32
U-87 MG
CHEMBL614247
 IC50 7.96 7.96 11.0 1
Vero
CHEMBL391
 IC50 7.8 7.8 16.0 1
Toxoplasma gondii
CHEMBL612888
 IC50 7.7 7.7 20.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1163130
 IC50 7.7 7.7 20.2 1
Lacticaseibacillus casei
CHEMBL613075
 IC50 7.57 7.57 27.0 1
Dihydrofolate reductase
CHEMBL2902
 IC50 7.57 7.075 27.0 2
Dihydrofolate reductase
CHEMBL2329
 IC50 7.4 7.4 40.0 1
Dihydrofolate reductase
CHEMBL2576
 IC50 7.38 7.38 42.0 1
KB
CHEMBL398
 IC50 7.24 7.025 58.0 2
D54 cell line
CHEMBL612247
 IC50 7.22 7.22 60.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 6.48 6.48 330.0 2
Homo sapiens
CHEMBL372
 IC50 6.12 6.115 750.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 0.77 mL.min-1.kg-1 Homo sapiens
CL 0.77 mL.min-1.kg-1 Homo sapiens
Fu 0.05 - Homo sapiens
MRT 17.0 hr Homo sapiens
T1/2 17.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 0.04 nM 10.4 Inhibition of DHFR (unknown origin) assessed as inhibition constant 33243532
Dihydrofolate reductase Ki = 0.06 nM 10.22 Inhibitory constant for murine Wild-type dihydrofolate reductase (DHFR) 12825924
Dihydrofolate reductase IC50 = 0.42 nM 9.38 Inhibition of human DHFR 34894691
Dihydrofolate reductase Ki = 0.71 nM 9.15 Binding affinity was reported with purified recombinant Pneumocystis carinii Dih... 7490723
Dihydrofolate reductase Ki = 0.81 nM 9.09 Inhibitory constant for F31A/F34A murine dihydrofolate reductase (DHFR) 12825924
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1.35 nM 8.87 Inhibition of Toxoplasma gondii DHFR-TS expressed in Escherichia coli BL21 compe... 30624926
Unchecked IC50 = 1.35 nM 8.87 TBD: TBD -
Dihydrofolate reductase Ki = 1.4 nM 8.85 Inhibition of human recombinant Dihydrofolate reductase enzyme 8632413
Unchecked IC50 = 1.4 nM 8.85 Inhibition of Toxoplasma gondii DHFR 34894691
Dihydrofolate reductase IC50 = 1.4 nM 8.85 Tested for inhibitory activity against dihydrofolate reductase in human 8230096
Dihydrofolate reductase IC50 = 1.5 nM 8.82 Inhibition of Mycobacterium avium DHFR at 37 degC by spectrophotometry 20056546
Dihydrofolate reductase IC50 = 1.5 nM 8.82 Inhibitory concentration against Mycobacterium avium dihydrofolate reductase 15026078
Dihydrofolate reductase IC50 = 1.5 nM 8.82 Inhibitory concentration against Dihydrofolate reductase from Mycobacterium aviu... 15214795
Dihydrofolate reductase IC50 = 1.5 nM 8.82 Concentration required to inhibit the Mycobacterium avium Dihydrofolate reductas... 15115391
Unchecked IC50 = 1.5 nM 8.82 Inhibition of Mycobacterium avium DHFR using dihydrofolic acid substrate and NAD... 18605720
Unchecked IC50 = 1.5 nM 8.82 Inhibition of Mycobacterium avium DHFR 23627352
HCT-8 IC50 = 1.8 nM 8.74 Activity was evaluated against HCT-8 tumor cells 8632413
Plasmodium falciparum IC50 = 1.9 nM 8.72 Antimalarial activity against pyrimethamine-sensitive Plasmodium falciparum 3D7 ... 19528269
Dihydrofolate reductase Ki = 1.9 nM 8.72 Inhibition of Dihydrofolate reductase enzyme from Candida albicans 8632413
Unchecked IC50 = 2.1 nM 8.68 Inhibition of Pneumocystis jirovecii DHFR expressed in Escherichia coli Rosetta-... 31176699

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
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
19528269 10.1128/aac.00308-09 Plasmodium falciparum 6
18680275 10.1021/jm8003366 NON-PROTEIN TARGET 5
23627352 10.1021/jm400086g Unchecked 5
12825924 10.1021/jm034057i Dihydrofolate reductase 5
9719595 10.1021/jm980081y Dihydrofolate reductase 5
7877140 10.1021/jm00005a002 Dihydrofolate reductase 5
8230096 10.1021/jm00073a009 Dihydrofolate reductase 4
8632413 10.1021/jm9505122 P388 4
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
17552508 10.1021/jm070165j Unchecked 3
12408727 10.1021/jm0202369 Dihydrofolate reductase 3
15115391 10.1021/jm030599o Unchecked 3
17552508 10.1021/jm070165j Dihydrofolate reductase 3
15115391 10.1021/jm030599o Dihydrofolate reductase 3
12408727 10.1021/jm0202369 Unchecked 3

Data from ChEMBL 36 via Core Engine