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Compound Detail

CHEMBL1117

IDARUBICIN
💊 Approved Drug
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💊 Approved Drug
CC(=O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1ccccc1C3=O

Basic Information

ChEMBL ID CHEMBL1117
Name IDARUBICIN
Phase Approved
Structure Type MOL
InChI Key XDXDZDZNSLXDNA-TZNDIEGXSA-N
Therapeutic ✓ Yes

Known Names

Idarubicin Idarubicina Idarubicine
13
Targets
42
Activities
1
Assay Types
29
PK Parameters
20
Publications
3
Known Names
20
Indications

Molecular Properties

497.5
MW (Da)
1.02
ALogP
10
HBA
5
HBD
176.6
PSA (Ų)
0.33
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -rubicin
USAN Year 1987

Extended Properties

Molecular Formula C26H27NO9
MW 497.50
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness 1.67

Indications

Neoplasms Anemia, Refractory Anemia, Refractory, with Excess of Blasts Leukemia Leukemia, Erythroblastic, Acute Leukemia, Erythroblastic, Acute Leukemia, Megakaryoblastic, Acute Leukemia, Monocytic, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myelomonocytic, Acute Leukemia, Myelomonocytic, Chronic Leukemia, Promyelocytic, Acute Lymphoma Lymphoma, Non-Hodgkin Multiple Myeloma Myelodysplastic Syndromes Myeloproliferative Disorders Myeloproliferative Disorders Neoplasms, Plasma Cell

ATC Classification

L01DB06
idarubicin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 42 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 9.15 7.4779 0.7 14
K562
CHEMBL385
IC50 8.7 7.6817 2.0 6
DNA topoisomerase 2-alpha
CHEMBL1806
IC50 8.59 8.59 2.6 1
U2OS
CHEMBL615023
IC50 7.62 7.62 24.0 1
MEL-JUSO
CHEMBL1075501
IC50 7.05 7.05 89.0 1
Unchecked
CHEMBL612545
IC50 6.16 5.765 700.0 4
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.64 5.57 2300.0 2
Mycolicibacterium smegmatis
CHEMBL613088
IC50 5.44 5.3 3610.0 6
SK-OV-3
CHEMBL614925
IC50 5.35 5.35 4500.0 1
Son of sevenless homolog 1
CHEMBL2079846
IC50 5.22 5.16 6000.0 2
Plasmodium berghei
CHEMBL612653
IC50 5.18 5.18 6620.0 1
MCF7
CHEMBL387
IC50 5.14 5.14 7300.0 1
HepG2
CHEMBL395
IC50 4.91 4.91 12300.0 1

Pharmacokinetic Data

Parameter Value Units Species
ALB_CHANGE - - Rattus norvegicus
ALB_CHANGE - - Rattus norvegicus
AUC 305.0 ug.ml-1 Canis lupus familiaris
CHOL_CHANGE - - Rattus norvegicus
CHOL_CHANGE - - Rattus norvegicus
CL 24.0 mL.min-1.kg-1 Homo sapiens
CL 24.0 mL.min-1.kg-1 Homo sapiens
Clp 711.0 ml.min-1 Canis lupus familiaris
Clp 6.0 ml.min-1 Canis lupus familiaris
F 28.0 % Homo sapiens
Fu 0.076 - Homo sapiens
Incidence - - Rattus norvegicus
Incidence - - Rattus norvegicus
Incidence - - Rattus norvegicus
Incidence - - Rattus norvegicus
Mortality - - Rattus norvegicus
MRT 26.0 hr Homo sapiens
PHOSLPD_CHANGE - - Rattus norvegicus
PHOSLPD_CHANGE - - Rattus norvegicus
T1/2 16.0 hr Homo sapiens
T1/2 0.1 hr Canis lupus familiaris
T1/2 18.9 hr Canis lupus familiaris
TRIG_CHANGE - - Rattus norvegicus
TRIG_CHANGE - - Rattus norvegicus
Vd 34.5 L.kg-1 Canis lupus familiaris
WBC_CHANGE 35.0 % Rattus norvegicus
WBC_CHANGE 50.0 % Rattus norvegicus
WBC_CHANGE 35.0 % Rattus norvegicus
WBC_CHANGE 55.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.71 nM 9.15 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.0 nM 9.0 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 1.05 nM 8.98 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.05 nM 8.98 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.17 nM 8.93 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.26 nM 8.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.41 nM 8.85 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
K562 IC50 = 2.0 nM 8.7 Cytotoxic activity against K562 erythroleukemic cells 10425093
DNA topoisomerase 2-alpha IC50 = 2.6 nM 8.59 Inhibition of Topo IIalpha (unknown origin) 37847948
K562 IC50 = 12.0 nM 7.92 Cytotoxicity against human K562 cells after 5 days by XTT assay 18076140
U2OS IC50 = 24.0 nM 7.62 Cytotoxicity against human U2OS cells incubated for 2 hrs by cell titre blue via... 37561481
K562 IC50 = 27.0 nM 7.57 Cytotoxicity against human K562 cells incubated for 2 hrs by cell titre blue via... 37561481
K562 IC50 = 27.0 nM 7.57 Cytotoxicity against human K562 cells incubated for 2 hrs followed by compound w... 39088428
K562 IC50 = 41.0 nM 7.39 Cytotoxicity against human K562 cells overexpressing ABCB1 incubated for 2 hrs f... 39088428
MEL-JUSO IC50 = 89.0 nM 7.05 Cytotoxicity against human MEL-JUSO cells incubated for 2 hrs by cell titre blue... 37561481
K562 IC50 = 116.0 nM 6.94 Cytotoxicity against human K562 cells overexpressing ABCG2 incubated for 2 hrs f... 39088428
Plasmodium falciparum IC50 = 630.96 nM 6.2 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 700.0 nM 6.16 Inhibition of NDM-1 (unknown origin) using nitrocefin as substrate preincubated ... 23591260
Unchecked IC50 = 890.0 nM 6.05 Displacement of SYBR from phage lambda DNA by FID assay 24900668
Plasmodium falciparum IC50 = 1000.0 nM 6.0 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 740
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19734910 10.1038/nchembio.215 Plasmodium falciparum 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
39088428 10.1021/acs.jmedchem.4c00614 ADMET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
24900668 10.1021/ml3002852 Unchecked 5
23591260 10.1016/j.bmc.2013.03.031 Unchecked 4
39088428 10.1021/acs.jmedchem.4c00614 K562 4
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
24900668 10.1021/ml3002852 ADMET 3
24900668 10.1021/ml3002852 NON-PROTEIN TARGET 3
33324471 10.1021/acsmedchemlett.0c00521 Unchecked 2
19445515 10.1021/jm900403j Homo sapiens 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
22586124 10.1073/pnas.1118370109 Plasmodium falciparum 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2

Data from ChEMBL 36 via Core Engine