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Compound Detail

CHEMBL1750

CLOFARABINE
💊 Approved Drug
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💊 Approved Drug
Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F

Basic Information

ChEMBL ID CHEMBL1750
Name CLOFARABINE
Phase Approved
Structure Type MOL
InChI Key WDDPHFBMKLOVOX-AYQXTPAHSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201370

Known Names

Clofarabina Clofarabine Clolar Evoltra Ivozall NSC-759857
14
Targets
29
Activities
2
Assay Types
1
PK Parameters
20
Publications
6
Known Names
20
Indications
3
Mechanisms

Molecular Properties

303.7
MW (Da)
-0.35
ALogP
8
HBA
3
HBD
119.3
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Prodrug
USAN Stem -arabine
USAN Year 2003

Extended Properties

Molecular Formula C10H11ClFN5O3
MW 303.68
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.63

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ribonucleoside-diphosphate reductase RR1 inhibitor INHIBITOR Ribonucleoside-diphosphate reductase RR1
DNA inhibitor INHIBITOR DNA
DNA polymerase (alpha/delta/epsilon) inhibitor INHIBITOR DNA polymerase (alpha/delta/epsilon)

Indications

Neoplasms Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Leukemia Leukemia, Myeloid, Acute Graft vs Host Disease Hematologic Diseases Histiocytosis, Langerhans-Cell Hodgkin Disease Leukemia, Biphenotypic, Acute Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Myelogenous, Chronic, BCR-ABL Positive Leukemia, Myelomonocytic, Chronic Lymphoma Lymphoma, Non-Hodgkin Multiple Myeloma Myelodysplastic Syndromes Osteopetrosis

ATC Classification

L01BB06
clofarabine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 28 meas. best 9.0
EC50 1 meas. best 4.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 9.0 7.8067 1.0 9
K562
CHEMBL385
IC50 8.52 8.52 3.0 2
HEp-2
CHEMBL614735
IC50 7.92 7.92 12.0 2
Granta
CHEMBL612254
IC50 7.77 7.77 17.0 1
HL-60
CHEMBL383
IC50 7.4 7.2 40.0 2
CCRF-CEM
CHEMBL382
IC50 7.36 7.2933 44.0 3
TC-32
CHEMBL4296499
IC50 6.89 6.89 130.0 1
L1210
CHEMBL386
IC50 6.64 6.64 230.0 2
RL
CHEMBL2366175
IC50 6.42 6.42 380.0 1
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
IC50 5.51 5.51 3120.0 2
A549
CHEMBL392
IC50 5.1 5.1 8000.0 1
Human immunodeficiency virus 1
CHEMBL378
EC50 4.52 4.52 30400.0 1
MCF7
CHEMBL387
IC50 4.3 4.3 50000.0 1
HeLa
CHEMBL399
IC50 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 57.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
K562 IC50 = 3.0 nM 8.52 Compound was tested for cytotoxicity against K562 cell lines 1732556
K562 IC50 = 3.0 nM 8.52 Anticancer activity against human K562 cells 34213340
Unchecked IC50 = 5.16 nM 8.29 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
HEp-2 IC50 = 12.0 nM 7.92 Compound was tested for cytotoxicity against HEp-2 cell lines 1732556
HEp-2 IC50 = 12.0 nM 7.92 Anticancer activity against human HEp-2 cells 34213340
Granta IC50 = 17.0 nM 7.77 Cytotoxicity against human Granta cells assessed as decrease in cell viability a... 30176535
HL-60 IC50 = 40.0 nM 7.4 Cytotoxicity against human HL60 cells assessed as decrease in cell viability aft... 30176535
CCRF-CEM IC50 = 44.0 nM 7.36 Cytotoxicity against human CCRF-CEM cells assessed as decrease in cell viability... 30176535
CCRF-CEM IC50 = 50.0 nM 7.3 Compound was tested for cytotoxicity against CCRF-CEM cell lines 1732556
CCRF-CEM IC50 = 60.0 nM 7.22 Anticancer activity against human CCRF-CEM cells 34213340
Unchecked IC50 = 65.0 nM 7.19 Inhibition of Ribonucleotide reductase (unknown origin) 33540357
Unchecked IC50 = 65.0 nM 7.19 Inhibition of Ribonucleoside-diphosphate reductase(unknown origin) 37801827
Unchecked IC50 = 90.0 nM 7.05 Cytotoxicity against human TC71 cells assessed as reduction in cell viability in... 36917882
HL-60 IC50 = 100.0 nM 7.0 Cytostatic activity against human HL60 cells after 48 hrs by MTT assay 23820572
TC-32 IC50 = 130.0 nM 6.89 Cytotoxicity against human TC-32 cells assessed as reduction in cell viability i... 36917882
Unchecked IC50 = 163.6 nM 6.79 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 180.0 nM 6.75 Cytotoxicity against human A4573 cells assessed as reduction in cell viability i... 36917882

Literature References

PubMed DOI Target Context # Activities
27117260 10.1016/j.bmc.2016.03.052 Unchecked 25
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
1732556 10.1021/jm00080a029 Mus musculus 12
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
36917882 10.1016/j.ejmech.2023.115244 TC-32 5
36917882 10.1016/j.ejmech.2023.115244 U2OS 4
20014752 10.1021/tx900326k Hepatotoxicity 3
27117260 10.1016/j.bmc.2016.03.052 Human immunodeficiency virus 1 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
29174506 10.1016/j.bmc.2017.11.022 cGMP-dependent 3',5'-cyclic phosphodiesterase 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine