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Merck
CN

SML1736

Nelarabine

≥98% (HPLC)

Synonym(s):

2-amino-9-β-D-arabinofuranosyl-6-methoxy-9H-purine, 506U, 506U78, 9-β-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine, Arranon, Atriance, GW-506U78

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About This Item

Empirical Formula (Hill Notation):
C11H15N5O5
CAS Number:
121032-29-9
Molecular Weight:
297.27
NACRES:
NA.77
UNSPSC Code:
12352200

Key Documents

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InChI

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 key

IXOXBSCIXZEQEQ-KBNQYOMWSA-N

SMILES string

O[C@@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C=NC3=C2N=C(N)N=C3OC

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Antineoplastic purine nucleoside analog used in T-cell acute lymphoblastic leukemia; pro-drug of Ara-G.
Nelarabine is an antineoplastic purine nucleoside analog used in T-cell acute lymphoblastic leukemia. It is a pro-drug of Ara-G, which is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. Incorporation of Ara-GTP into DNA leads to inhibition of DNA synthesis and apoptosis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000437874
0000437874
0000232308
0000232308
0000126507

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Stuart S Winter et al.
Pediatric blood & cancer, 62(7), 1176-1183 (2015-03-11)
Nelarabine has shown impressive single agent clinical activity in T-cell acute lymphoblastic leukemia (T-ALL), but has been associated with significant neurotoxicities in heavily pre-treated patients. We showed previously that it was safe to add nelarabine to a BFM-86 chemotherapy backbone
Larry W Buie et al.
Clinical therapeutics, 29(9), 1887-1899 (2007-11-24)
Nelarabine was approved by the US Food and Drug Administration (FDA) in October 2005 for the treatment of T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL) that has not responded to or has relapsed after treatment with at
Nelarabine, cyclosphosphamide and etoposide for adults with relapsed T-cell acute lymphoblastic leukaemia and lymphoma.
Marlise R Luskin et al.
British journal of haematology, 174(2), 332-334 (2015-09-26)

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