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Compound Detail

CHEMBL260046

EVOFOSFAMIDE
🧪 Phase III
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🧪 Phase III
Cn1c(COP(=O)(NCCBr)NCCBr)cnc1[N+](=O)[O-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL260046
Name EVOFOSFAMIDE
Phase Phase III
Structure Type MOL
InChI Key UGJWRPJDTDGERK-UHFFFAOYSA-N
Active Moiety CHEMBL4802229

Known Names

Evofosfamida Evofosfamide HAP-302 TH-302
9
Targets
25
Activities
1
Assay Types
0
PK Parameters
20
Publications
4
Known Names
8
Indications
1
Mechanisms

Molecular Properties

449.0
MW (Da)
1.92
ALogP
6
HBA
2
HBD
111.3
PSA (Ų)
0.24
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product Prodrug
USAN Stem -fos-; -fosfamide
USAN Year 2014

Extended Properties

Molecular Formula C9H16Br2N5O4P
MW 449.04
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -0.46

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Biliary Tract Neoplasms Glioblastoma Melanoma Sarcoma Esophageal Neoplasms Multiple Myeloma Neoplasms Pancreatic Neoplasms

Activity Summary

IC50 25 meas. best 8.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-468
CHEMBL614335
 IC50 8.21 6.785 6.2 2
NCI-H460
CHEMBL396
 IC50 8.03 5.7313 9.3 8
SW-620
CHEMBL612262
 IC50 7.28 5.985 52.0 2
H-EMC-SS
CHEMBL1075451
 IC50 6.89 6.215 130.0 2
Alpha-enolase
CHEMBL3298
 IC50 6.52 5.87 301.0 4
Unchecked
CHEMBL612545
 IC50 6.39 5.945 404.0 2
DU-145
CHEMBL613508
 IC50 5.38 5.38 4140.0 1
PC-3
CHEMBL390
 IC50 5.19 5.19 6490.0 1
HT-29
CHEMBL384
 IC50 4.3 4.3 49510.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-468 IC50 = 6.2 nM 8.21 Cytotoxicity against human MDA-MB-468 cells incubated for 4 hrs under hypoxic co... 30885680
NCI-H460 IC50 = 9.3 nM 8.03 Cytotoxicity against human NCI-H460 cells after 24 hrs under hypoxic condition b... 29079474
NCI-H460 IC50 = 19.0 nM 7.72 Cytotoxicity against human H460 cells under hypoxic condition after 2 hrs by Ala... 18257544
SW-620 IC50 = 52.0 nM 7.28 Cytotoxicity against human SW620 cells incubated for 4 hrs under hypoxic conditi... 30885680
H-EMC-SS IC50 = 130.0 nM 6.89 Antiproliferative activity against human HEMC-SS cells treated for 24 hrs under ... 30199705
Alpha-enolase IC50 = 301.0 nM 6.52 Inhibition of ENO1 in overexpressed human D423 cells incubated for 5 days in pre... 32676158
Unchecked IC50 = 404.0 nM 6.39 Cytotoxicity against human D423 cells with ENO1 deficient assessed as reduction ... 32676158
Alpha-enolase IC50 = 897.0 nM 6.05 Inhibition of ENO1 in wild-type human LN319 cells incubated for 5 days in presen... 32676158
NCI-H460 IC50 = 2000.0 nM 5.7 Antiproliferative activity against human NCI-H460 cells in presence of N2 30295477
Alpha-enolase IC50 = 2554.0 nM 5.59 Inhibition of ENO1 in overexpressed human D423 cells incubated for 5 days in pre... 32676158
H-EMC-SS IC50 = 2900.0 nM 5.54 Antiproliferative activity against human HEMC-SS cells treated for 24 hrs under ... 30199705
Unchecked IC50 = 3202.0 nM 5.5 Cytotoxicity against human D423 cells with ENO1 deficient assessed as reduction ... 32676158
DU-145 IC50 = 4140.0 nM 5.38 Cytotoxicity against human DU145 cells incubated for 2 hrs under hypoxic conditi... 29259746
MDA-MB-468 IC50 = 4403.0 nM 5.36 Cytotoxicity against human MDA-MB-468 cells incubated for 4 hrs under aerobic co... 30885680
Alpha-enolase IC50 = 4838.0 nM 5.32 Inhibition of ENO1 in wild-type human LN319 cells incubated for 5 days in presen... 32676158
NCI-H460 IC50 = 5100.0 nM 5.29 Cytotoxicity against human H460 cells under normoxic condition after 2 hrs by Al... 18257544
PC-3 IC50 = 6490.0 nM 5.19 Cytotoxicity against human PC3 cells incubated for 2 hrs under hypoxic condition... 29259746
NCI-H460 IC50 = 6650.0 nM 5.18 Cytotoxicity against human NCI-H460 cells after 24 hrs under normoxic condition ... 29079474
NCI-H460 IC50 = 9080.0 nM 5.04 Cytotoxicity against human NCI-H460 cells pretreated for 24 hrs under hypoxic co... 28350997
SW-620 IC50 = 20600.0 nM 4.69 Cytotoxicity against human SW620 cells incubated for 4 hrs under aerobic conditi... 30885680

Literature References

PubMed DOI Target Context # Activities
18257544 10.1021/jm701028q NCI-H460 6
29079474 10.1016/j.bmcl.2017.10.023 Unchecked 5
32676158 10.1021/acsmedchemlett.0c00203 Alpha-enolase 4
18257544 10.1021/jm701028q HT-29 3
30885680 10.1016/j.bmcl.2019.03.015 SW-620 3
30885680 10.1016/j.bmcl.2019.03.015 MDA-MB-468 3
28350997 10.1016/j.ejmech.2017.03.040 HT-29 3
28350997 10.1016/j.ejmech.2017.03.040 NCI-H460 3
29259746 10.1021/acsmedchemlett.7b00355 PC-3 3
29259746 10.1021/acsmedchemlett.7b00355 DU-145 3
30295477 10.1021/acs.jmedchem.8b00147 NCI-H460 3
30199705 10.1016/j.ejmech.2018.08.060 H-EMC-SS 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32676158 10.1021/acsmedchemlett.0c00203 Unchecked 2
29079474 10.1016/j.bmcl.2017.10.023 NCI-H460 2
18257544 10.1021/jm701028q Mus musculus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
29079474 10.1016/j.bmcl.2017.10.023 No relevant target 1
18257544 10.1021/jm701028q MIA PaCa-2 1

Data from ChEMBL 36 via Core Engine