General
Preferred name
NELARABINE
Synonyms
GW 506U78 ()
Nelzarabine ()
506U78 ()
Nelarabine (Arranon) ()
Arranon ()
S1213 ()
506U78,Arranon ()
NSC-759876 ()
Atriance ()
NSC-755985 ()
MAY ()
GW-506U78 ()
506U ()
Attriance ()
NSC-686673 ()
P&D ID
PD003304
CAS
121032-29-9
Tags
prodrug
natural product
drug
available
Approved by
EMA
FDA
First approval
2005
Drug Status
investigational
approved
Drug indication
Antineoplastic
leukaemia
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION This compound is a prodrug. The active metabolite is its 5'-triphosphate, ara-GTP. (GtoPdb)
PHARMACODYNAMICS Nelarabine is a prodrug of the cytotoxic deoxyguanosine analogue 9-ß-D-arabinofuranosylguanine (ara-G). Nelarabine is demethylated by adenosine deaminase (ADA) to ara-G. Ara-G is then transported into cells, where it undergoes three phosphorylation steps, resulting in the formation of ara-G triphosphate (ara-GTP). In the first phosphorylation step, ara-G is converted to ara-G monophosphate (ara-GMP). Ara-GMP is then monophosphorylated by deoxyguanosine kinase and deoxycytidine kinase to ara-G diphosphate, and then subsequently to the active ara-G triphosphate (ara-GTP). Ara-GTP is the one that exerts the pharmacological effect. Pre-clinical studies have demonstrated that targeted T-cells possess marked sensitivity to the agent.
DESCRIPTION deoxyguanosine analog; inhibitor of DNA synthesis (Informer Set)
DESCRIPTION Enhances hPSC differentiation into cranial placode cells (Tocris Bioactive Compound Library)
Cell lines
2
Organisms
0
Compound Sets
21
AdooQ Bioactive Compound Library
A10632
Cayman Chemical Bioactives
20248
ChEMBL Approved Drugs
CHEMBL1201112
ChEMBL Drugs
CHEMBL1201112
Drug Repurposing Hub
DrugBank
DB01280
DrugBank Approved Drugs
DB01280
DrugCentral
1892
DrugCentral Approved Drugs
1892
DrugMAP
DMB6VEG
DrugMAP Approved Drugs
DMB6VEG
Guide to Pharmacology
7090
Informer Set
660391
NCATS Inxight Approved Drugs
60158CV180
NIH Approved Oncology Drugs
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Arranon
TargetMol Bioactive Compound Library
T6603
Tocris Bioactive Compound Library
6359
External IDs
40
Properties
(calculated by RDKit )
Molecular Weight
297.11
Hydrogen Bond Acceptors
10
Hydrogen Bond Donors
4
Rotatable Bonds
3
Ring Count
3
Aromatic Ring Count
2
cLogP
-1.97
TPSA
148.77
Fraction CSP3
0.55
Chiral centers
4.0
Largest ring
6.0
QED
0.51
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
POLA1
DNA synthesis (ALL-SIL cells)
DNA synthesis (HSB2 cells)
DNA synthesis (JURKAT cells)
DNA synthesis (PER-255 cells)
DNA/RNA Synthesis
Compound status
FDA
Pathway
DNA Damage/DNA Repair
Primary Target
DNA, RNA and Protein Synthesis
MOA
Inhibitor
DNA/RNA Synthesis inhibitor
DNA synthesis inhibitor, T cell inhibitor
Indication
acute lymphoblastic leukemia (ALL)
Therapeutic Class
Anticancer Agents
Source data