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Nelarabine

CAT: 0013-GTR19161135-02Size: 2 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161135-02Size:2 mg
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Description
Nelarabine is a purine nucleoside analog that is used as a cytotoxic agent in hematological malignancies. Nelarabine is converted into arabinosyl-guanine (ara-G) in the blood, and ara-G is selectively accumulated in T cells and malignant T-lymphoid cells, where it is phosphorylated to produce ara-GTP and incorporated into DNA. (In Vitro) :Nelarabine (506U78) (0-20 μM; 48 h) induces cytotoxic effects in T-ALL cell lines.Nelarabine (5 or 2 μM; 48 h) promotes apoptosis in sensitive T-ALL cell lines and modulates PI3K/AKT/mTOR and MEK signaling.Nelarabine (10 μM; 0-48 h) resistance does not depend on expression of ENT1/2 transporters and is partly due to upregulation of PI3K, MEK, and Bcl2 signaling. (In Vivo) :Nelarabine (506U78) (130 mg/kg/day; i.v.; 5 days) reduces leukemic burden and extends mouse survival in NSG mice xenografted with luciferase-expressing U937 cells.
CAS Number
121032-29-9
Product Name Alternative
Arranon, 506U78, GW506U78 | GW-506U78
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO : 9.8 mg/mL. 32.97 mM
Smiles
COC1=NC (N) =NC2=C1N=CN2[C@@H]1O[C@H] (CO) [C@@H] (O) [C@@H]1O
Molecular Formula
C11H15N5O5
Molecular Weight
297.27
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(2R,3S,4R,5R) -2- (2-amino-6-methoxy-9H-purin-9-yl) -5- (hydroxymethyl) tetrahydrofuran-3,4-diol

Chemical Information

Nelarabine

Nelarabine is a purine nucleoside in which O-methylguanine is attached to arabinofuranose via a beta-N9-glycosidic bond. Inhibits DNA synthesis and causes cell death; a prodrug of 9-beta-D-arabinofuranosylguanine (ara-G). It has a role as an antineoplastic agent, a prodrug and a DNA synthesis inhibitor. It is a purine nucleoside, a beta-D-arabinoside and a monosaccharide derivative. It is functionally related to a guanine and a 9-beta-D-arabinofuranosylguanine.

CAS Number121032-29-9
PubChem CID3011155
IUPAC Name(2R,3S,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular FormulaC11H15N5O5
Molecular Weight297.27
XLogP-0.7
Topological Polar Surface Area149
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Heavy Atom Count21
Formal Charge0
Complexity377
SMILES
COC1=NC(=NC2=C1N=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N
InChI
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
InChIKey
IXOXBSCIXZEQEQ-UHTZMRCNSA-N
Chemical Structure
2D Structure
2D structure of Nelarabine
CAS: 121032-29-9
CID: 3011155
Formula: C11H15N5O5
MW: 297.27
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight297.27
XLogP3-0.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass297.10731860
Monoisotopic Mass297.10731860
Topological Polar Surface Area149 Ų
Heavy Atom Count21
Formal Charge0
Complexity377
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
A1379-5.1Nelarabine

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