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Compound Detail

CHEMBL1096882

FLUDARABINE PHOSPHATE
💊 Approved Drug
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💊 Approved Drug
Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1096882
Name FLUDARABINE PHOSPHATE
Phase Approved
Structure Type MOL
InChI Key GIUYCYHIANZCFB-FJFJXFQQSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL4570249

Known Names

2-f-ara-amp Fludara Fludarabine 5'-monophosphate Fludarabine monophosphate Fludarabine phosphate NSC-312887 NSC-328002 Oforta
10
Targets
14
Activities
2
Assay Types
5
PK Parameters
20
Publications
8
Known Names
20
Indications
2
Mechanisms

Molecular Properties

365.2
MW (Da)
-1.72
ALogP
10
HBA
5
HBD
186.1
PSA (Ų)
0.31
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Prodrug
USAN Stem -arabine
USAN Year 1982

Extended Properties

Molecular Formula C10H13FN5O7P
MW 365.21
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 1.09

Mechanism of Action

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

Indications

Leukemia, Lymphocytic, Chronic, B-Cell Neoplasms Neoplasms Anemia, Aplastic Anemia, Aplastic Anemia, Refractory Anemia, Refractory, with Excess of Blasts Bone Marrow Failure Disorders Hodgkin Disease Leukemia Leukemia, Erythroblastic, Acute Leukemia, Megakaryoblastic, Acute Leukemia, Monocytic, Acute Leukemia, Myelogenous, Chronic, BCR-ABL Positive Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myelomonocytic, Acute Leukemia, Myelomonocytic, Chronic Lymphoma Lymphoma, Follicular

ATC Classification

L01BB05
fludarabine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States

Activity Summary

IC50 13 meas. best 7.05
Ki 1 meas. best 6.88

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HL-60
CHEMBL383
 IC50 7.05 7.05 90.0 1
MCF7
CHEMBL387
 IC50 6.89 6.89 130.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 6.88 6.88 130.9 1
K562
CHEMBL385
 IC50 6.82 6.61 150.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.82 5.94 150.0 4
CCRF-CEM
CHEMBL382
 IC50 6.4 6.4 400.0 1
Raji
CHEMBL614628
 IC50 6.4 6.4 400.0 1
ZR-75-1
CHEMBL614393
 IC50 6.22 6.22 600.0 1
L1210
CHEMBL386
 IC50 5.52 5.52 3000.0 1
HEp-2
CHEMBL614735
 IC50 5.05 5.05 9000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 17000.0 ng.hr.mL-1 Rattus norvegicus
AUC 17790.0 ng.hr.mL-1 Mus musculus
Cmax 24613.24 nM Mus musculus
T1/2 1.5 hr Mus musculus
Tmax 0.9 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HL-60 IC50 = 90.0 nM 7.05 Antiproliferative activity against human HL60 cells assessed as cell growth inhi... 25960323
MCF7 IC50 = 130.0 nM 6.89 Antiproliferative activity against human MCF7 cells assessed as cell growth inhi... 25960323
Carbonic anhydrase 5A, mitochondrial Ki = 130.9 nM 6.88 Inhibition of recombinant human carbonic anhydrase VA preincubated with enzyme f... 31387062
NON-PROTEIN TARGET IC50 = 150.0 nM 6.82 Antiproliferative activity against human KG1 cells assessed as cell growth inhib... 25960323
K562 IC50 = 150.0 nM 6.82 Anticancer activity against human K562 cells 34213340
Raji IC50 = 400.0 nM 6.4 Antiproliferative activity against human Raji cells assessed as cell growth inhi... 25960323
K562 IC50 = 400.0 nM 6.4 Antiproliferative activity against human K562 cells assessed as cell growth inhi... 25960323
CCRF-CEM IC50 = 400.0 nM 6.4 Anticancer activity against human CCRF-CEM cells 34213340
ZR-75-1 IC50 = 600.0 nM 6.22 Antiproliferative activity against human ZR-75-1 cells assessed as cell growth i... 25960323
NON-PROTEIN TARGET IC50 = 950.0 nM 6.02 Antiproliferative activity against human MOLT3 cells assessed as cell growth inh... 25960323
NON-PROTEIN TARGET IC50 = 2000.0 nM 5.7 Antiproliferative activity against human M-HeLa cells assessed as cell growth in... 25960323
L1210 IC50 = 3000.0 nM 5.52 Anticancer activity against mouse L1210 cells 34213340
NON-PROTEIN TARGET IC50 = 6000.0 nM 5.22 Antiproliferative activity against human SK-UT-1B cells assessed as cell growth ... 25960323
HEp-2 IC50 = 9000.0 nM 5.05 Anticancer activity against human HEp-2 cells 34213340

Literature References

PubMed DOI Target Context # Activities
25960323 10.1016/j.bmc.2015.04.059 Mus musculus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
25960323 10.1016/j.bmc.2015.04.059 NON-PROTEIN TARGET 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
25960323 10.1016/j.bmc.2015.04.059 HL-60 1
25960323 10.1016/j.bmc.2015.04.059 Raji 1

Data from ChEMBL 36 via Core Engine