Nelarabine (CED0007366)

Record Information
Version1.0
Creation Date2016-05-22 05:59:33 UTC
Update Date2026-05-14 16:59:18 UTC
Accession NumberCHEM019294
Identification
Common NameNelarabine
ClassSmall Molecule
Description
Nelarabine is an organic compound with the formula C11H15N5O5 and an average molecular weight of 297.27 g/mol. Nelarabine belongs to the purine nucleosides, a class of nucleosides, nucleotides, and analogues within the organic compounds. Used as an antineoplastic agent within healthcare, pharmaceuticals, and veterinary products, this compound is administered via intravenous exposure. Nelarabine acts on four recorded protein targets, serving as an inhibitor of DNA ligase 1 (LIG1), the DNA primase small subunit (PRIM1), the ribonucleoside-diphosphate reductase large subunit (RRM1), and the DNA polymerase alpha catalytic subunit (POLA1).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purineChEBI
ArranonChEBI
NelzarabineChEBI
2-Amino-9-b-D-arabinofuranosyl-6-methoxy-9H-purineGenerator
2-Amino-9-β-D-arabinofuranosyl-6-methoxy-9H-purineGenerator
GW-506U78HMDB
Compound 506u78HMDB
2-Amino-6-methoxypurine arabinosideHMDB
GlaxoSmithKline brand OF nelarabineHMDB
Chemical FormulaC11H15N5O5
Average Molecular Mass297.267 g/mol
Monoisotopic Mass297.107 g/mol
CAS Registry Number121032-29-9
IUPAC Name(2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional Namenelarabine
SMILESCOC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
InChI KeyIXOXBSCIXZEQEQ-UHTZMRCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Hypoxanthine
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Alkyl aryl ether
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Heteroaromatic compound
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.9 g/LALOGPS
logP-0.81ALOGPS
logP-1.6ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity69.6 m³·mol⁻¹ChemAxon
Polarizability27.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ab9-9160000000-faf81feea076fd7f2c2eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0w30-4902300000-00b862d4b042b6caeb64Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1910000000-d09b09e2c32a65f2ac55Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0940000000-05786731bc8af4c9273cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-c1582ed3900ea73a1a3aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-0900000000-862068247f35d06ca7cfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ot-0590000000-efa66ff74370c360726cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-0910000000-87f932f5a7438fca86ccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2900000000-cfa051ab5e966ccd6168Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-7f20cf9333bbb1eb98e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-49bf916fd47c2c0647daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1900000000-8261e4d55d25a6e7e406Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0590000000-3e9e0887473f63d8445eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-0910000000-b322547ac26e69901a1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-1910000000-eb40dee5635f93bf37eaNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2125.0Log mg/kg[1200:3800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
2 pathways
Nelarabine Action Pathway
Nelarabine Action Pathway
Nelarabine Drug Metabolism Action Pathway
Nelarabine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)14.2464
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)11.9888
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)10.1204
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)14.0907
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)16.8154
Heat shock protein HSP 90-alpha structureClick to view 3D structureHeat shock protein HSP 90-alphaP07900HumansPredicted (SEA)3.58106
Endoplasmin structureClick to view 3D structureEndoplasminP14625HumansPredicted (SEA)2.49118
Click to view 3D structureAdenosine receptor A3P28647Rattus norvegicusPredicted (SEA)9.88685
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)3.50322
Click to view 3D structureAdenosine deaminaseP56658Bos taurusPredicted (SEA)1.01204
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)20.2408
Click to view 3D structureAdenosine receptor A1P28190Bos taurusPredicted (SEA)10.6653
High affinity choline transporter 1 structureClick to view 3D structureHigh affinity choline transporter 1Q9GZV3HumansPredicted (SEA)2.49118
Click to view 3D structureAdenosine receptor A1P49892Gallus gallusPredicted (SEA)4.7488
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)70.2978
Click to view 3D structureAdenosine receptor A2aP46616Cavia porcellusPredicted (SEA)6.30579
Click to view 3D structureAdenosine receptor A3Q61618Mus musculusPredicted (SEA)11.4438
Click to view 3D structureAdenosine receptor A1Q60612Mus musculusPredicted (SEA)10.8989
Click to view 3D structureNAD kinaseQ5HH78Staphylococcus aureus (strain COL)Predicted (SEA)2.33548
Click to view 3D structureNAD kinase 1Q8Y8D7Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)Predicted (SEA)2.33548
Click to view 3D structureAdenosine kinaseP9WID5Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)3.19182
Adenosine kinase structureClick to view 3D structureAdenosine kinaseP55263HumansPredicted (SEA)3.42537
Equilibrative nucleoside transporter 1 structureClick to view 3D structureEquilibrative nucleoside transporter 1Q99808HumansPredicted (SEA)3.11397
Click to view 3D structureAdenosine kinaseQ9TVW2Toxoplasma gondiiPredicted (SEA)2.80257
P2Y purinoceptor 1 structureClick to view 3D structureP2Y purinoceptor 1P47900HumansPredicted (SEA)14.6357
Concentrations
Not Available
External Links
DrugBank IDDB01280
HMDB IDHMDB0015401
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNelarabine
Chemspider ID2280207
ChEBI ID63612
PubChem Compound ID3011155
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gandhi V, Keating MJ, Bate G, Kirkpatrick P: Nelarabine. Nat Rev Drug Discov. 2006 Jan;5(1):17-8.
2. Roecker AM, Allison JC, Kisor DF: Nelarabine: efficacy in the treatment of clinical malignancies. Future Oncol. 2006 Aug;2(4):441-8.
3. Buie LW, Epstein SS, Lindley CM: Nelarabine: a novel purine antimetabolite antineoplastic agent. Clin Ther. 2007 Sep;29(9):1887-99.
4. Sanford M, Lyseng-Williamson KA: Nelarabine. Drugs. 2008;68(4):439-47.
5. Curbo S, Karlsson A: Nelarabine: a new purine analog in the treatment of hematologic malignancies. Rev Recent Clin Trials. 2006 Sep;1(3):185-92.
6. Cooper TM: Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. Ther Clin Risk Manag. 2007 Dec;3(6):1135-41.
7. Sigalas P, Tourvas AD, Moulakakis A, Pangalis G, Kontopidou F: Nelarabine induced complete remission in an adult with refractory T-lineage acute lymphoblastic leukemia: A case report and review of the literature. Leuk Res. 2009 Jul;33(7):e61-3. doi: 10.1016/j.leukres.2008.12.005. Epub 2009 Jan 21.
8. DeAngelo DJ: Nelarabine for the treatment of patients with relapsed or refractory T-cell acute lymphoblastic leukemia or lymphoblastic lymphoma. Hematol Oncol Clin North Am. 2009 Oct;23(5):1121-35, vii-viii. doi: 10.1016/j.hoc.2009.07.008.
9. Reilly KM, Kisor DF: Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. Onco Targets Ther. 2009 Feb 18;2:219-28.
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18586926
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19825456
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20043113
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=20528871
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20616909
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=20796200
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=21151585
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21190039
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21320002
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21353591
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21715318
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21730354
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=21737993
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22184539
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=63612