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Compound Detail

CHEMBL70927

DEFERIPRONE
💊 Approved Drug
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💊 Approved Drug
Cc1c(O)c(=O)ccn1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL70927
Name DEFERIPRONE
Phase Approved
Structure Type MOL
InChI Key TZXKOCQBRNJULO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

APO-066 APO-66 CP-20 CP20 Deferipron Deferiprona Deferiprone Deferiprone lipomed DN-180-01-AF DN-18001AF Ferriprox L-1 +4 more
17
Targets
28
Activities
2
Assay Types
1
PK Parameters
20
Publications
16
Known Names
16
Indications
1
Mechanisms

Molecular Properties

139.2
MW (Da)
0.40
ALogP
3
HBA
1
HBD
42.2
PSA (Ų)
0.56
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -iprone
USAN Year 2008

Extended Properties

Molecular Formula C7H9NO2
MW 139.15
Aromatic Rings 1
Heavy Atoms 10
NP-Likeness -0.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Anemia, Sickle Cell beta-Thalassemia beta-Thalassemia Iron Overload Thalassemia Acute Kidney Injury Hemochromatosis Pantothenate Kinase-Associated Neurodegeneration Amyotrophic Lateral Sclerosis Friedreich Ataxia Parkinson Disease Stroke HIV Infections Myocardial Infarction Cerebellar Ataxia Cognitive Dysfunction

ATC Classification

V03AC02
deferiprone
Level 1: VARIOUS
Level 2: ALL OTHER THERAPEUTIC PRODUCTS

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States

Activity Summary

IC50 24 meas. best 6.7
EC50 4 meas. best 4.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L1210
CHEMBL386
 IC50 6.7 4.78 200.0 5
Aspergillus fumigatus
CHEMBL363
 IC50 5.89 5.89 1290.0 1
Lysine-specific demethylase 4A
CHEMBL5896
 IC50 5.49 5.485 3220.0 2
Rattus norvegicus
CHEMBL376
 IC50 5.41 5.41 3900.0 2
Lysine-specific demethylase 6A
CHEMBL2069164
 IC50 5.38 5.38 4200.0 1
Deoxyhypusine hydroxylase
CHEMBL4523441
 IC50 5.3 5.3 5000.0 1
Lysine-specific demethylase 5C
CHEMBL2163176
 IC50 5.25 5.25 5600.0 1
Lysine-specific demethylase 2A
CHEMBL1938210
 IC50 5.17 5.17 6800.0 1
Lysine-specific demethylase 2B
CHEMBL3779760
 IC50 5.09 5.09 8100.0 1
No relevant target
CHEMBL2362975
 IC50 5.01 4.905 9700.0 2
A-375
CHEMBL613859
 IC50 4.57 4.57 27240.0 1
Mushroom tyrosinase
CHEMBL6066154
 IC50 4.52 4.52 30000.0 1
HEK-293T
CHEMBL3706568
 EC50 4.4 4.4 40000.0 1
Rattus norvegicus
CHEMBL376
 EC50 4.33 4.33 46700.0 1
HeLa
CHEMBL399
 IC50 4.21 4.21 61840.0 1
MCF7
CHEMBL387
 IC50 4.19 4.19 64950.0 1
Unchecked
CHEMBL612545
 EC50 4.19 4.19 64000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.17 4.17 67500.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 13.0 uM Agaricus bisporus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L1210 IC50 = 200.0 nM 6.7 Antiproliferative activity against mouse L1210 cells 19601577
Aspergillus fumigatus IC50 = 1290.0 nM 5.89 Antifungal activity against Aspergillus fumigatus B5233 conidia after 16 hrs by ... 19307370
Lysine-specific demethylase 4A IC50 = 3220.0 nM 5.49 Inhibition of KDM4A (unknown origin) measured by formaldehyde dehydrogenase (FDH... 35838529
Lysine-specific demethylase 4A IC50 = 3330.0 nM 5.48 Inhibition of KDM4A (unknown origin) measured by LANCEUltra assay 35838529
Rattus norvegicus IC50 = 3900.0 nM 5.41 Compound was tested for 50% Inhibition of lipid peroxidation in rat brain homoge... 10956184
Rattus norvegicus IC50 = 3900.0 nM 5.41 Compound was tested for its inhibitory activity against lipid peroxidation in ra... 12392736
Lysine-specific demethylase 6A IC50 = 4200.0 nM 5.38 Inhibition of KDM6A (unknown origin) 35101649
Deoxyhypusine hydroxylase IC50 = 5000.0 nM 5.3 Inhibition of DOHH (unknown origin) 30684796
Lysine-specific demethylase 5C IC50 = 5600.0 nM 5.25 Inhibition of KDM5C (unknown origin) 35101649
Lysine-specific demethylase 2A IC50 = 6800.0 nM 5.17 Inhibition of KDM2A (unknown origin) 35101649
Lysine-specific demethylase 2B IC50 = 8100.0 nM 5.09 Inhibition of KDM2B (unknown origin) 35101649
No relevant target IC50 = 9700.0 nM 5.01 Antioxidant activity assessed as ABTS radical scavenging activity incubated in d... 37976709
No relevant target IC50 = 15950.0 nM 4.8 Antioxidant activity assessed as ABTS radical scavenging activity incubated for ... 37976703
A-375 IC50 = 27240.0 nM 4.57 Cytotoxicity against human A-375 cells assessed as reduction in cell viability p... 38626642
Mushroom tyrosinase IC50 = 30000.0 nM 4.52 Inhibition of mushroom Tyrosinase 37487307
HEK-293T EC50 = 40000.0 nM 4.4 Protection against cisplatin-induced cytotoxicity in HEK293T cells assessed as c... 37976709
L1210 IC50 = 46000.0 nM 4.34 Inhibitory concentration against growth of murine L1210 cells at 48 hours 15943485
L1210 IC50 = 46000.0 nM 4.34 Compound was tested for the growth inhibition of L1210 cell at a duration of 48 ... 14640556
Rattus norvegicus EC50 = 46700.0 nM 4.33 Ability to protect cerebellar granule cells (CGC) from iodoacetate (IAA)-induced... 10956184
L1210 IC50 = 55000.0 nM 4.26 Compound was tested for the growth inhibition of L1210 cell at a duration of 96 ... 14640556

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32208614 10.1021/acs.jmedchem.0c00137 ADMET 11
37976709 10.1016/j.ejmech.2023.115945 No relevant target 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
31325784 10.1016/j.ejmech.2019.07.031 No relevant target 7
8289206 10.1021/jm00027a011 Rattus norvegicus 6
32503694 10.1016/j.bmc.2020.115550 No relevant target 6
17869385 10.1016/j.ejmech.2007.07.011 No relevant target 6
10579844 10.1021/jm991080o No relevant target 6
10579844 10.1021/jm991080o ADMET 5
9719587 10.1021/jm9707784 No relevant target 5
7509878 10.1021/jm00030a005 ADMET 5
14640556 10.1021/jm0302694 L1210 5
15943485 10.1021/jm048974f L1210 5
28061347 10.1016/j.ejmech.2016.12.045 No relevant target 4
32866008 10.1021/acs.jmedchem.0c00763 No relevant target 4
23266185 10.1016/j.bmc.2012.11.009 Unchecked 4
8355246 10.1021/jm00069a002 No relevant target 4
9719587 10.1021/jm9707784 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine