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Compound Detail

CHEMBL1619

CLADRIBINE
💊 Approved Drug
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💊 Approved Drug
Nc1nc(Cl)nc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1619
Name CLADRIBINE
Phase Approved
Structure Type MOL
InChI Key PTOAARAWEBMLNO-KVQBGUIXSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL4594368

Known Names

2-cda Cladaribine Cladribina Cladribine Leustat Leustatin Litak Mavenclad NSC-05014 NSC-105014 NSC-105014-F RWJ 26251 +1 more
33
Targets
75
Activities
3
Assay Types
6
PK Parameters
20
Publications
13
Known Names
20
Indications
1
Mechanisms

Molecular Properties

285.7
MW (Da)
-0.30
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 1993
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -ribine
USAN Year 1992

Extended Properties

Molecular Formula C10H12ClN5O3
MW 285.69
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness 0.76

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Anemia Immune System Diseases Leukemia, Hairy Cell Multiple Sclerosis Neoplasms Leukemia Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Myeloid, Acute Lymphoma Lymphoma, T-Cell, Peripheral Multiple Sclerosis, Relapsing-Remitting Cholangitis, Sclerosing Histiocytosis Histiocytosis, Langerhans-Cell Leukemia, Biphenotypic, Acute Leukemia, Myeloid Lymphoma, B-Cell, Marginal Zone Lymphoma, Mantle-Cell Mastocytosis, Systemic Multiple Sclerosis, Chronic Progressive

ATC Classification

L01BB04
cladribine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS
L04AA40
cladribine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 69 meas. best 9.3
Ki 4 meas. best 8.64
EC50 2 meas. best 5.53

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CCRF-CEM
CHEMBL382
 IC50 9.3 8.78 0.5 3
BV-173
CHEMBL2366145
 IC50 9.1 9.1 0.8 1
Purine nucleoside phosphorylase
CHEMBL4338
 Ki 8.64 8.64 2.3 1
Raji
CHEMBL614628
 IC50 8.05 8.05 9.0 1
HEp-2
CHEMBL614735
 IC50 7.52 7.52 30.0 2
HepG2
CHEMBL395
 IC50 7.4 6.7333 40.0 3
L1210
CHEMBL386
 IC50 7.16 6.91 70.0 3
Hep 3B2
CHEMBL4296437
 IC50 7.0 7.0 100.0 2
Mahlavu
CHEMBL4296473
 IC50 7.0 7.0 100.0 1
BT-549
CHEMBL614072
 IC50 6.91 6.91 123.0 1
CT26
CHEMBL613866
 IC50 6.88 6.88 131.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.78 6.1 165.0 10
K562
CHEMBL385
 IC50 6.77 5.6267 170.0 3
HCT-116
CHEMBL394
 IC50 6.52 5.775 300.0 2
Huh-7
CHEMBL614039
 IC50 6.4 6.105 400.0 4
Unchecked
CHEMBL612545
 IC50 6.4 5.6117 400.0 6
Jurkat
CHEMBL397
 IC50 6.18 6.18 660.0 1
T47D
CHEMBL614361
 IC50 6.16 6.16 700.0 1
EL4
CHEMBL614293
 IC50 6.07 6.07 848.0 1
MCF7
CHEMBL387
 IC50 5.7 5.45 2000.0 6
SNU-475
CHEMBL1075586
 IC50 5.6 5.6 2500.0 2
TC-32
CHEMBL4296499
 IC50 5.54 5.54 2920.0 1
Unchecked
CHEMBL612545
 EC50 5.53 5.425 2958.0 2
SNU-423
CHEMBL1075584
 IC50 5.17 5.17 6700.0 2
SNU-387
CHEMBL1075583
 IC50 5.15 5.15 7100.0 2
Adenosine receptor A1
CHEMBL318
 Ki 5.13 5.13 7320.0 1
PC-3
CHEMBL390
 IC50 5.08 5.08 8280.0 1
PLC
CHEMBL613522
 IC50 5.04 5.04 9100.0 2
C6
CHEMBL614657
 IC50 5.04 5.04 9070.0 1
HPAC
CHEMBL612595
 IC50 5.03 5.03 9320.0 1
HT-29
CHEMBL384
 IC50 5.03 5.03 9440.0 1
Adenosine receptor A2a
CHEMBL302
 Ki 4.69 4.69 20400.0 1
SNU-182
CHEMBL4296495
 IC50 4.63 4.63 23300.0 2
SNU-449
CHEMBL1075585
 IC50 4.43 4.43 37300.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
F 40.0 % Homo sapiens
Fu 0.79 - Homo sapiens
MRT 9.2 hr Homo sapiens
T1/2 16.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CCRF-CEM IC50 = 0.5 nM 9.3 Cytotoxicity against human CCRF-CEM cells after 72 hrs by MTT assay 21840722
BV-173 IC50 = 0.8 nM 9.1 Cytotoxicity against human BV173 cells after 3 days by MTT assay 21711054
Purine nucleoside phosphorylase Ki = 2.3 nM 8.64 Binding affinity to PNP (unknown origin) assessed as inhibition constant by fluo... 38701712
CCRF-CEM IC50 = 3.0 nM 8.52 Compound was tested for cytotoxicity against CCRF-CEM cell lines 1732556
CCRF-CEM IC50 = 3.0 nM 8.52 Anticancer activity against human CCRF-CEM cells 34213340
Raji IC50 = 9.0 nM 8.05 Cytotoxicity against human Raji cells after 72 hrs by MTT assay 21840722
HEp-2 IC50 = 30.0 nM 7.52 Compound was tested for cytotoxicity against HEp-2 cell lines 1732556
HEp-2 IC50 = 30.0 nM 7.52 Anticancer activity against human HEp-2 cells 34213340
HepG2 IC50 = 40.0 nM 7.4 Antiproliferative activity against human HepG2 cells after 72 hrs by SRB assay 29326016
L1210 IC50 = 70.0 nM 7.16 Compound was tested for cytotoxicity against L1210 cell lines 1732556
L1210 IC50 = 70.0 nM 7.16 Anticancer activity against mouse L1210 cells 34213340
Hep 3B2 IC50 = 100.0 nM 7.0 Cytotoxicity against human Hep3B cells assessed as cell growth inhibition incuba... 38107180
Hep 3B2 IC50 = 100.0 nM 7.0 Cytotoxicity against human Hep3B cells assessed as cell growth inhibition incuba... 38688437
Mahlavu IC50 = 100.0 nM 7.0 Antiproliferative activity against human Mahlavu cells after 72 hrs by SRB assay 29326016
BT-549 IC50 = 123.0 nM 6.91 Cytotoxicity against human BT549 cells after 3 days by MTT assay 21711054
CT26 IC50 = 131.0 nM 6.88 Cytotoxicity against mouse CT26 cells after 3 days by MTT assay 21711054
NON-PROTEIN TARGET IC50 = 165.0 nM 6.78 Cytotoxicity against human MES-SA cells after 3 days by MTT assay 21711054
K562 IC50 = 170.0 nM 6.77 Cytotoxicity against human paclitaxel resistant K562 cells after 3 days by MTT a... 21711054
NON-PROTEIN TARGET IC50 = 200.0 nM 6.7 Antiproliferative activity against human KG1 cells assessed as cell growth inhib... 25960323
NON-PROTEIN TARGET IC50 = 285.0 nM 6.54 Cytotoxicity against mouse P388D1 cells after 3 days by MTT assay 21711054

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19929004 10.1021/jm901428k CCRF-CEM 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 15
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18570408 10.1021/jm800134t Unchecked 6
18570408 10.1021/jm800134t Deoxycytidine kinase 6
25960323 10.1016/j.bmc.2015.04.059 NON-PROTEIN TARGET 5
21711054 10.1021/jm2005173 NON-PROTEIN TARGET 5
9873575 10.1016/s0960-894x(98)00452-1 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
17526755 10.1128/aac.00081-07 Streptococcus sp. 3
25462277 10.1016/j.ejmech.2014.10.080 NON-PROTEIN TARGET 2
29174506 10.1016/j.bmc.2017.11.022 cGMP-dependent 3',5'-cyclic phosphodiesterase 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
17526755 10.1128/aac.00081-07 Staphylococcus aureus 2
21711054 10.1021/jm2005173 K562 2
19445515 10.1021/jm900403j Homo sapiens 2

Data from ChEMBL 36 via Core Engine