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Compound Detail

CHEMBL53418

DANTHRON
💊 Approved Drug
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💊 Approved Drug
O=C1c2cccc(O)c2C(=O)c2c(O)cccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL53418
Name DANTHRON
Phase Approved
Structure Type MOL
InChI Key QBPFLULOKWLNNW-UHFFFAOYSA-N

Known Names

Danthron Dantron Dantrone Dorbane Istizin NSC-38626 NSC-646568 Pilules vinchy n.f.
3
Targets
5
Activities
1
Assay Types
0
PK Parameters
20
Publications
8
Known Names
1
Indications
1
Mechanisms

Molecular Properties

240.2
MW (Da)
1.87
ALogP
4
HBA
2
HBD
74.6
PSA (Ų)
0.63
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C14H8O4
MW 240.21
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness 0.82

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Retinoid X receptor alpha antagonist ANTAGONIST Retinoic acid receptor RXR-alpha ✓ ✓

Indications

Constipation

ATC Classification

A06AB03
dantron
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR CONSTIPATION
A06AB53
dantron, combinations
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR CONSTIPATION

Drug Warnings

Withdrawn
carcinogenicity
Carcinogenicity
Country: United States; Canada; Singapore   Year: 1988
Withdrawn
carcinogenicity
Potential carcinogenicity
Country: United States; Canada; Singapore   Year: 1988
Withdrawn
carcinogenicity
May have a carcinogenic potential
Country: United States; Canada; Singapore   Year: 1988

Activity Summary

IC50 5 meas. best 5.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.24 4.97 5700.0 2
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 4.97 4.97 10700.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 4.23 4.23 58700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 5700.0 nM 5.24 Antiangiogenic activity against BAEC assessed as inhibition of bFGF-induced cell... 12350162
Amine oxidase [flavin-containing] A IC50 = 10700.0 nM 4.97 Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI inse... 34915314
NON-PROTEIN TARGET IC50 = 20100.0 nM 4.7 Antiangiogenic activity against BAEC assessed as inhibition of bFGF-induced cell... 12350162
Amine oxidase [flavin-containing] B IC50 = 58700.0 nM 4.23 Inhibition of recombinant human MAO-B expressed in baculovirus infected BTI inse... 34915314

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
619147 10.1021/jm00199a005 No relevant target 10
21531052 10.1016/j.ejmech.2011.03.034 Nucleic Acid 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2558164 10.1021/np50065a012 Unchecked 4
2558164 10.1021/np50065a012 Raji 4
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1016/j.cropro.2011.09.009 Trichoplusia ni 3
2213033 10.1021/np50069a014 NON-PROTEIN TARGET 3
17689076 10.1016/j.bmcl.2006.12.071 Pseudomonas aeruginosa 3
17689076 10.1016/j.bmcl.2006.12.071 Proteus mirabilis 3
17689076 10.1016/j.bmcl.2006.12.071 Proteus vulgaris 3
17689076 10.1016/j.bmcl.2006.12.071 Escherichia coli 3
11459643 10.1016/s0960-894x(01)00318-3 Estrogen receptor 3
11140730 10.1016/s0960-894x(00)00599-0 ADMET 3
11262091 10.1021/jm001073w ADMET 3
27884693 10.1016/j.bmcl.2016.11.029 Macrophage scavenger receptor types I and II 3
12350162 10.1021/np010577+ NON-PROTEIN TARGET 2
22680914 10.1021/np300074z Plasmodium falciparum 2
22680914 10.1021/np300074z ADMET 2

Data from ChEMBL 36 via Core Engine