Nelarabine

Names

[ Name ]:
Nelarabine

[Synonym ]:
2-Amino-9-b-D-arabinofuranosyl-6-methoxy-9H-purine
2-Amino-6-methoxypurinribonucleosid
506u
MAY
9-(β-D-Arabinofuranosyl)-6-methoxy-9H-purin-2-amine
9-b-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine
(2R,3S,4S,5R)-2-(2-Amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
9-β-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine
(2R,3S,4S,5R)-2-(2-amino-6-méthoxy-9H-purin-9-yl)-5-(hydroxyméthyl)tétrahydrofurane-3,4-diol
Nelzarabine
9beta-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine
9H-Purin-2-amine, 9-β-D-arabinofuranosyl-6-methoxy-
Nelarabine
O6-methyl-guanosine
Arranon
GW 506U78

Biological Activity

[Description]:

Nelarabine (Arranon, 506U78) is a purine nucleoside analog and DNA synthesis inhibitor with IC50 from 0.067-2.15 μM in tumor cells. Nelarabine is a chemotherapy drug used in T-cell acute lymphoblastic leukemia. IC50 Value: 0.44 uM (HSB2 cell lines); 1.24 μM(ALL-SIL cell lines); 2.15 μM(JURKAT cell lines); 0.067 uM (PER-255 cell lines) [1]Target: Nucleoside antimetabolite/analogin vitro: The IC50 of Nelarabine is 25-fold and 113-fold higher than ARAC in T- and B-lineage, respectively. T-ALL cells are eightfold more sensitive to Nelarabine than B-lineage but there is considerable overlap. The efficacy of NEL in T-lineage and B-lineage cell lines is 25-fold and 113-fold less than ARAC, respectively [1].in vivo: The median age was 34 years (range, 16-66 years); 32 (82%) patients were male. The rate of complete remission was 31% (95% confidence interval [CI], 17%, 48%) and the overall response rate was 41% (95% CI, 26%, 58%). The principal toxicity was grade 3 or 4 neutropenia and thrombocytopenia, occurring in 37% and 26% of patients, respectively [2]. Nelarabine has activity in T-cell malignancies, as evaluated in 2 Phase I and 5 Phase II studies. It received accelerated approval from the FDA based on the resuits of 2 Phase II trials, one in pediatric patients (PGAA 2001) and the other in adults (CALGB 19801)Toxicity: The principal toxicity was grade 3 or 4 neutropenia and thrombocytopenia, occurring in 37% and 26% of patients, respectively [2].Clinical trial: Drug Use Investigation for Arranon G (Nelarabine) Injection 250 mg.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Cancer

[References]

[1]. Beesley AH, et al. In vitro cytotoxicity of nelarabine, clofarabine and flavopiridol in paediatric acute lymphoblastic leukaemia. Br J Haematol. 2007 Apr;137(2):109-16.

[2]. DeAngelo DJ, et al. Nelarabine induces complete remissions in adults with relapsed or refractory T-lineage acute lymphoblastic leukemia or lymphoblastic lymphoma: Cancer and Leukemia Group B study 19801. Blood. 2007 Jun 15;109(12):5136-42.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
721.0±70.0 °C at 760 mmHg

[ Melting Point ]:
209-217ºC

[ Molecular Formula ]:
C₁₁H₁₅N₅O₅

[ Molecular Weight ]:
297.267

[ Flash Point ]:
389.9±35.7 °C

[ Exact Mass ]:
297.107330

[ PSA ]:
148.77000

[ LogP ]:
-0.58

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.829

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi