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Compound Detail

CHEMBL25336

BISANTRENE
🧪 Phase III
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🧪 Phase III
C(=N/NC1=NCCN1)\c1c2ccccc2c(/C=N/NC2=NCCN2)c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL25336
Name BISANTRENE
Phase Phase III
Structure Type MOL
InChI Key NJSMWLQOCQIOPE-OCHFTUDZSA-N

Known Names

Bisantrene Bisantreno
10
Targets
12
Activities
1
Assay Types
0
PK Parameters
20
Publications
2
Known Names
1
Indications
2
Mechanisms

Molecular Properties

398.5
MW (Da)
1.76
ALogP
8
HBA
4
HBD
97.6
PSA (Ų)
0.31
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Year 1981

Extended Properties

Molecular Formula C22H22N8
MW 398.47
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.41

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Alpha-ketoglutarate-dependent dioxygenase FTO inhibitor INHIBITOR Alpha-ketoglutarate-dependent dioxygenase FTO ✓ ✓
DNA disrupting agent DISRUPTING AGENT DNA ✓ ✓

Indications

Leukemia, Myeloid, Acute

Activity Summary

IC50 12 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A549
CHEMBL392
 IC50 7.77 7.77 17.0 1
RPMI-8226
CHEMBL614882
 IC50 7.75 6.395 18.0 2
L1210
CHEMBL386
 IC50 7.31 6.405 49.0 2
SW480
CHEMBL612544
 IC50 7.05 7.05 90.0 1
OCI-AML2
CHEMBL2366220
 IC50 7.0 7.0 100.0 1
RNA demethylase ALKBH5
CHEMBL3621037
 IC50 6.85 6.85 140.0 1
HL-60
CHEMBL383
 IC50 6.52 6.52 300.0 1
A2780
CHEMBL614004
 IC50 6.47 6.47 340.0 1
WiDr
CHEMBL614647
 IC50 6.1 6.1 790.0 1
NAD(P)H dehydrogenase [quinone] 1
CHEMBL3623
 IC50 4.6 4.6 25000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A549 IC50 = 17.0 nM 7.77 Compound was tested for potency against human lung A549 cells using sulforhodami... 9371238
RPMI-8226 IC50 = 18.0 nM 7.75 Compound was tested for potency against human myeloma 8226 cells using MTT assay... 9371238
L1210 IC50 = 49.0 nM 7.31 Compound was tested for potency against multidrug-resistant murine leukemia L121... 9371238
SW480 IC50 = 90.0 nM 7.05 Compound was tested for potency against human colon carcinoma SW 480 cells in a ... 9371238
OCI-AML2 IC50 = 100.0 nM 7.0 Antiproliferative activity against human OCI-AML2 cells assessed as reduction in... 38805939
RNA demethylase ALKBH5 IC50 = 140.0 nM 6.85 Inhibition of ALKBH5 (66 to 292 residues)(unknown origin) expressed in Escherich... 38805939
HL-60 IC50 = 300.0 nM 6.52 Cell cytotoxicity was determined against human promyelocytic leukemia (HL60) cel... 9871638
A2780 IC50 = 340.0 nM 6.47 Cell cytotoxicity was determined against human ovarian cancer (A2780) cell line 9871638
WiDr IC50 = 790.0 nM 6.1 Compound was tested for potency against human colon carcinoma WiDr cells in a su... 9371238
L1210 IC50 = 3200.0 nM 5.5 Compound was tested for potency against multi drug resistant murine leukemia L12... 9371238
RPMI-8226 IC50 = 9100.0 nM 5.04 Compound was tested for potency against human myeloma 8226 cells (40 fold resist... 9371238
NAD(P)H dehydrogenase [quinone] 1 IC50 = 25000.0 nM 4.6 Inhibition of human recombinant NQO1 17011189

Literature References

PubMed DOI Target Context # Activities
6806475 10.1021/jm00347a006 Mus musculus 17
2441053 10.1021/jm00391a009 RPMI-8226 13
2441053 10.1021/jm00391a009 L1210 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
8340913 10.1021/jm00067a007 Mus musculus 4
2342051 10.1021/jm00168a005 Nucleic Acid 3
9733500 10.1021/jm980167r Salmonella typhimurium 3
9871638 10.1016/s0960-894x(97)10207-4 DNA topoisomerase II 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
9371238 10.1021/jm970308+ L1210 2
9371238 10.1021/jm970308+ RPMI-8226 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
2441053 10.1021/jm00391a009 Unchecked 2
9871638 10.1016/s0960-894x(97)10207-4 A2780 1
9371238 10.1021/jm970308+ WiDr 1
38805939 10.1016/j.ejmech.2024.116526 OCI-AML2 1
2342051 10.1021/jm00168a005 Ovarian cancer cell line 1

Data from ChEMBL 36 via Core Engine