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Compound Detail

CHEMBL1201746

PRALATREXATE
💊 Approved Drug
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💊 Approved Drug
C#CCC(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201746
Name PRALATREXATE
Phase Approved
Structure Type MOL
InChI Key OGSBUKJUDHAQEA-WMCAAGNKSA-N
Therapeutic ✓ Yes

Known Names

Folotyn NSC-754230 PDX Pralatrexate Pralatrexato
11
Targets
17
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names
19
Indications
1
Mechanisms

Molecular Properties

477.5
MW (Da)
0.98
ALogP
9
HBA
5
HBD
207.3
PSA (Ų)
0.26
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Prescription
Chirality Racemic

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -trexate
USAN Year 2004

Extended Properties

Molecular Formula C23H23N7O5
MW 477.48
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.20

Mechanism of Action

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

Indications

Lymphoma, T-Cell Lymphoma, T-Cell, Peripheral Lymphoma, T-Cell, Peripheral Neoplasms Neoplasms Lymphoma Breast Neoplasms Carcinoma, Non-Small-Cell Lung Head and Neck Neoplasms Leukemia-Lymphoma, Adult T-Cell Lung Neoplasms Fallopian Tube Neoplasms Lymphoma, Large-Cell, Anaplastic Lymphoma, T-Cell, Cutaneous Multiple Myeloma Mycosis Fungoides Ovarian Neoplasms Peritoneal Neoplasms Sezary Syndrome

ATC Classification

L01BA05
pralatrexate
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 14 meas. best 9.33
Ki 2 meas. best 10.87
EC50 1 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 10.87 10.87 0.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 10.87 10.87 0.0 1
KB
CHEMBL398
 IC50 9.33 9.02 0.5 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.16 7.97 0.7 2
Reduced folate transporter
CHEMBL4833
 IC50 9.16 9.16 0.7 1
SARS-CoV-2
CHEMBL4303835
 EC50 8.1 8.1 8.0 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.24 7.24 57.0 1
R2
CHEMBL614385
 IC50 7.24 7.24 57.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 7.22 7.22 60.0 2
Folate receptor alpha
CHEMBL2121
 IC50 6.78 6.78 168.0 1
Unchecked
CHEMBL612545
 IC50 6.09 6.09 819.0 1
ADMET
CHEMBL612558
 IC50 6.09 6.09 819.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.0134 nM 10.87 Binding affinity to Plasmodium falciparum DHFR assessed as inhibition constant 37801827
Dihydrofolate reductase Ki = 0.0134 nM 10.87 Inhibition of DHFR (unknown origin) at pH 6.7 33540357
KB IC50 = 0.47 nM 9.33 Growth inhibition of human KB cells expressing human RFC/FRalpha/PCFT after 96 h... 24111942
KB IC50 = 0.47 nM 9.33 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 29425443
NON-PROTEIN TARGET IC50 = 0.69 nM 9.16 Growth inhibition of Chinese hamster PC43-10 cells after 96 hrs by CellTiter-blu... 24111942
Reduced folate transporter IC50 = 0.69 nM 9.16 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 29425443
KB IC50 = 1.94 nM 8.71 Growth inhibition of human KB cells expressing human RFC/FRalpha/PCFT after 96 h... 24111942
KB IC50 = 1.94 nM 8.71 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 29425443
SARS-CoV-2 EC50 = 8.0 nM 8.1 Antiviral activity against SARS-CoV-2 infected in African green monkey Vero cell... 38522112
R2 IC50 = 57.0 nM 7.24 Growth inhibition of Chinese hamster R2 cells expressing human PCFT4 after 96 hr... 24111942
Proton-coupled folate transporter IC50 = 57.0 nM 7.24 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29425443
SARS-CoV-2 IC50 = 60.0 nM 7.22 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
SARS-CoV-2 IC50 = 60.0 nM 7.22 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
NON-PROTEIN TARGET IC50 = 168.0 nM 6.78 Growth inhibition of Chinese hamster RT16 cells after 96 hrs by CellTiter-blue a... 24111942
Folate receptor alpha IC50 = 168.0 nM 6.78 Binding affinity to human FR-alpha receptor expressed in Chinese hamster RT16 ce... 29425443
ADMET IC50 = 819.0 nM 6.09 Growth inhibition of Chinese hamster MTXRII-OuaR2-4 cells after 96 hrs by CellTi... 24111942
Unchecked IC50 = 819.0 nM 6.09 Cytotoxicity in RFC-null Chinese hamster R2 cells assessed as reduction in cell ... 29425443

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
24111942 10.1021/jm401139z NON-PROTEIN TARGET 5
24111942 10.1021/jm401139z ADMET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 ADMET 2
- 10.6019/CHEMBL4495565 Vero C1008 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
29425443 10.1021/acs.jmedchem.7b01708 KB 2
29425443 10.1021/acs.jmedchem.7b01708 Folate receptor beta 2
29425443 10.1021/acs.jmedchem.7b01708 Folate receptor alpha 2
29425443 10.1021/acs.jmedchem.7b01708 Unchecked 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
24111942 10.1021/jm401139z KB 2
29425443 10.1021/acs.jmedchem.7b01708 Proton-coupled folate transporter 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
29425443 10.1021/acs.jmedchem.7b01708 Reduced folate transporter 1
24111942 10.1021/jm401139z R2 1
33540357 10.1016/j.ejmech.2021.113218 Dihydrofolate reductase 1
- 10.6019/EOS300033 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine