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Compound Detail

CHEMBL1568

FLUDARABINE
🧪 Phase III
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🧪 Phase III
Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1568
Name FLUDARABINE
Phase Phase III
Structure Type MOL
InChI Key HBUBKKRHXORPQB-FJFJXFQQSA-N

Known Names

2-f-araa 2-fluoro ara-a 2-fluorovidarabine Fludarabina Fludarabine Fluradosa NSC-118218 NSC-118218H
27
Targets
63
Activities
3
Assay Types
14
PK Parameters
20
Publications
8
Known Names
20
Indications

Molecular Properties

285.2
MW (Da)
-1.84
ALogP
9
HBA
4
HBD
139.5
PSA (Ų)
0.47
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -arabine

Extended Properties

Molecular Formula C10H12FN5O4
MW 285.24
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 1.06

Indications

Anemia, Aplastic Anemia, Aplastic Anemia, Sickle Cell Leukemia Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Myelogenous, Chronic, BCR-ABL Positive Leukemia, Myeloid, Acute Lymphoma Lymphoma, Follicular Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Lymphoma, Mantle-Cell Lymphoma, Non-Hodgkin Melanoma Melanoma Melanoma Multiple Myeloma Myelodysplastic Syndromes Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma

Activity Summary

IC50 50 meas. best 6.82
EC50 8 meas. best 6.8
Ki 5 meas. best 8.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL318
 Ki 8.23 8.23 5.9 1
Adenosine receptor A2a
CHEMBL302
 Ki 7.55 7.55 28.0 1
K562
CHEMBL385
 IC50 6.82 6.7 150.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.8 5.7971 160.0 7
SNU-398
CHEMBL614454
 IC50 6.7 6.7 200.0 2
CCRF-CEM
CHEMBL382
 IC50 6.4 5.555 400.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.0 5.1333 1010.0 3
PBMC
CHEMBL613107
 IC50 5.72 5.19 1900.0 3
L1210
CHEMBL386
 IC50 5.52 5.52 3000.0 1
HCT-116
CHEMBL394
 IC50 5.1 5.0933 8000.0 3
Unchecked
CHEMBL612545
 IC50 5.07 4.9475 8449.6 4
HEp-2
CHEMBL614735
 IC50 5.05 5.05 9000.0 1
Mahlavu
CHEMBL4296473
 IC50 5.0 4.9 10000.0 3
Adenosine receptor A3
CHEMBL3360
 Ki 4.98 4.98 10400.0 1
MCF7
CHEMBL387
 IC50 4.82 4.82 15000.0 3
HeLa
CHEMBL399
 EC50 4.8 4.8 16000.0 1
HepG2
CHEMBL395
 IC50 4.77 4.7467 17000.0 3
Huh-7
CHEMBL614039
 IC50 4.61 4.56 24400.0 3
SNU-449
CHEMBL1075585
 IC50 4.6 4.6 25100.0 2
Hep 3B2
CHEMBL4296437
 IC50 4.56 4.56 27800.0 2
SNU-423
CHEMBL1075584
 IC50 4.49 4.49 32600.0 2
SNU-387
CHEMBL1075583
 IC50 4.47 4.47 33800.0 2
SNU-182
CHEMBL4296495
 IC50 4.43 4.43 37200.0 2
SNU-475
CHEMBL1075586
 IC50 4.38 4.38 41500.0 2
PLC
CHEMBL613522
 IC50 4.38 4.38 41700.0 2
T47D
CHEMBL614361
 IC50 4.33 4.33 46200.0 1
A549
CHEMBL392
 IC50 4.32 4.32 47440.0 1
5'-nucleotidase
CHEMBL5957
 Ki 3.3 3.175 500000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 65700.0 ng.hr.mL-1 Mus musculus
AUC 39600.0 ng.hr.mL-1 Mus musculus
AUC 2490.0 ng.hr/g Mus musculus
AUC 11300.0 ng.hr/g Mus musculus
CL 3.2 mL.min-1.kg-1 Homo sapiens
Cmax 801.0 ng/g Mus musculus
Cmax 6050.0 ng/g Mus musculus
Fu 0.76 - Homo sapiens
MRT 12.0 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
T1/2 2.2 hr Mus musculus
T1/2 1.7 hr Mus musculus
Tmax 1.63 hr Mus musculus
Tmax 0.88 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 5.9 nM 8.23 Binding affinity to adenosine A1 receptor in rat brain membranes by measuring di... 7707320
Adenosine receptor A2a Ki = 28.0 nM 7.55 Binding affinity to adenosine A2A receptor in rat striatal membranes by measurin... 7707320
K562 IC50 = 150.0 nM 6.82 Compound was tested for cytotoxicity against K562 cell lines 1732556
NON-PROTEIN TARGET EC50 = 160.0 nM 6.8 Antitumor activity against CLL5 cells isolated from CLL patient assessed as cell... 24673739
SNU-398 IC50 = 200.0 nM 6.7 Cytotoxicity against human SNU-398 cells assessed as cell growth inhibition incu... 38688437
SNU-398 IC50 = 200.0 nM 6.7 Cytotoxicity against human SNU-398 cells assessed as cell growth inhibition incu... 38107180
K562 IC50 = 260.0 nM 6.58 Cytotoxicity against human paclitaxel-resistant K562 cells after 72 hrs by MTT a... 20605656
NON-PROTEIN TARGET EC50 = 350.0 nM 6.46 Antitumor activity against CLL3 cells isolated from CLL patient assessed as cell... 24673739
CCRF-CEM IC50 = 400.0 nM 6.4 Compound was tested for cytotoxicity against CCRF-CEM cell lines 1732556
NON-PROTEIN TARGET EC50 = 640.0 nM 6.19 Antitumor activity against CLL4 cells isolated from CLL patient assessed as cell... 24673739
NON-PROTEIN TARGET IC50 = 1010.0 nM 6.0 Cytotoxicity against human CEM-DNR-B cells after 72 hrs by MTT assay 20605656
NON-PROTEIN TARGET EC50 = 1600.0 nM 5.8 Antitumor activity against CLL6 cells isolated from CLL patient assessed as cell... 24673739
PBMC IC50 = 1900.0 nM 5.72 Cytotoxicity against patient PBMC after 48 hrs by CellTitre-Blue assay 25562417
NON-PROTEIN TARGET EC50 = 2660.0 nM 5.58 Antitumor activity against CLL2 cells isolated from CLL patient assessed as cell... 24673739
L1210 IC50 = 3000.0 nM 5.52 Compound was tested for cytotoxicity against L1210 cell lines 1732556
NON-PROTEIN TARGET IC50 = 6600.0 nM 5.18 Cytotoxicity against human HCT116 cells after 72 hrs by SRB assay 25462277
HCT-116 IC50 = 8000.0 nM 5.1 Antiproliferative activity against human HCT116 cells after 72 hrs by SRB assay 29326016
HCT-116 IC50 = 8000.0 nM 5.1 Cytotoxicity against human HCT-116 cells assessed as cell growth inhibition incu... 38688437
HCT-116 IC50 = 8300.0 nM 5.08 Cytotoxicity against human HCT-116 cells assessed as cell growth inhibition incu... 38107180
Unchecked IC50 = 8449.6 nM 5.07 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
20605656 10.1016/j.ejmech.2010.05.003 CCRF-CEM 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23388705 10.1124/dmd.112.049858 Mus musculus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
24673739 10.1021/jm4016922 NON-PROTEIN TARGET 7
23388705 10.1124/dmd.112.049858 Brain 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
18426954 10.1124/dmd.108.020479 ADMET 4
25562417 10.1021/jm501848m PBMC 3
12617912 10.1016/s0960-894x(03)00011-8 K562 3
17526755 10.1128/aac.00081-07 Streptococcus sp. 3
25562417 10.1021/jm501848m NON-PROTEIN TARGET 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
20605656 10.1016/j.ejmech.2010.05.003 K562 2
25462277 10.1016/j.ejmech.2014.10.080 NON-PROTEIN TARGET 2
17526755 10.1128/aac.00081-07 Staphylococcus aureus 2
4068000 10.1021/jm00149a033 Adenosine deaminase 2
30798051 10.1016/j.ejmech.2019.02.040 5'-nucleotidase 2

Data from ChEMBL 36 via Core Engine