Compound: Nelarabine
SMILES: O1[C@@H](n2c3nc(nc(c3nc2)OC)N)[C@@H](O)[C@@H]([C@H]1CO)O
InChIKey: IXOXBSCIXZEQEQ-UHTZMRCNSA-N
Synonyms: Nelarabine, 121032-29-9, Nelzarabine, Arranon, Atriance, 506U78, 506U, GW-506U78, Attriance, NSC-686673, GW506U78, 2-Amino-6-methoxypurine arabinoside, compound 506U78, Nelarabina, 2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purine, NSC-755985, (2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, DTXSID6046842, CHEBI:63612, NSC-759876, 60158CV180, DTXCID4026842, (2R,3S,4S,5R)-2-(hydroxymethyl)-5-(2-imino-6-methoxy-3,9-dihydro-2H-purin-9-yl)oxolane-3,4-diol, nelarabinum, NSC686673, nelarabine injection, RefChem:832139, L01BB07, 2-Amino, 6-Methoxypurine Arabinoside, 642-916-9, 9-beta-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, C11H15N5O5, MFCD00871078, Nelarabine (Arranon), 9H-Purin-2-amine, 9-b-D-arabinofuranosyl-6-methoxy-, (2R,3S,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, GW 506U78, MAY, NCGC00181098-01, S1213, Nelarabine [USAN], ArranonG, (2R,3S,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, SMR002544682, Arranon (TN), Nelzarabine (USAN), CAS-121032-29-9, Nelarabine [USAN:INN:BAN], GW-506U, UNII-60158CV180, Nelarabine [INN], 9beta-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine, NSC 686673, Nelarabine (Standard), NELARABINE [MI], NELARABINE [JAN], NELARABINE [VANDF], NELARABINE [MART.], NELARABINE [WHO-DD], SCHEMBL18820, MLS003915614, MLS004774135, MLS006010906, Nelarabine (JAN/USAN/INN), NELARABINE [EMA EPAR], GTPL7090, orb1300623, 9-(beta-D-arabinofuranosyl)-6-methoxy-9H-purin-2-amine, CHEMBL1201112, NELARABINE [ORANGE BOOK], SCHEMBL29374016, EX-A7779L, HMS3715I16, (2R,3R,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol, Tox21_112714, BDBM50247985, EBC-11246, HY-13701R, NSC755985, 2-(2-Amino-6-methoxy-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol, AKOS015852325, AKOS015920191, Tox21_112714_1, CCG-267441, CS-1607, DB01280, NN26176, NCGC00274059-01, NCGC00274059-02, AS-47664, BP-58633, HY-13701, SY227007, N1144, SW218086-2, D05134, F15095, AB01274773-01, AB01274773_02, EN300-7361965, F093678, SR-01000931847, 9-b-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine, Q1216264, SR-01000931847-3, 2-Amino-6-methoxy-9-b-D-arabinofuranosyl-9 H-purine, 2-Amino-6-methoxy-9-b-D-arabinofuranosyl-9H-purine, 9-|A-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine, BRD-K84466663-001-01-3, BRD-K84466663-001-05-4, 2-Amino-6-methoxy-9-beta-D-arabinofuranosyl-9H-purine, 9-beta -D-arabinofuranosyl-2-amino-6-methoxy-9H-purine, 9-beta-D-arabinofuranosyl-2-amino-6-methoxy-9 H-purine, 9H-Purin-2-amine, 9beta-D-arabinofuranosyl-6-methyl-, 2-Amino-6-methoxy-9-(beta-D-arabinofuranosyl)-9H-purine, 2-AMINO-9-.BETA.-D-ARABINOFURANOSYL-6-METHOXY-9H-PURINE, 9-.BETA.-D-ARABINOFURANOSYL-6-METHOXY-9H-PURIN-2-AMINE, 9H-PURIN-2-AMINE, 9-.BETA.-D-ARABINOFURANOSYL-6-METHOXY-
Theoretical properties:
molecular_formula: C11H15N5O5
molecular_weight: 297.27 g/mol
exact_mass: 297.10731860 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 3
heavy_atom_count: 21
topological_polar_surface_area: 149 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 209-217 °C (with decomposition)
solubility: Slightly soluble to soluble in water
Descriptions:
pubchem: 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.
chebi: A purine nucleoside in which <em>O</em>-methylguanine is attached to arabinofuranose via a β-<em>N</em><small><sup>9</small></sup>-glycosidic bond. Inhibits DNA synthesis and causes cell death; a prodrug of 9-β-<small>D</small>-arabinofuranosylguanine (ara-G).
chembl: NELARABINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Nelarabine, sold under the brand names Arranon (US) and Atriance (EU), is a chemotherapy medication used for the treatment of T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL).
Nelarabine is a prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity. Pre-clinical studies suggest that T-cells are particularly sensitive to nelarabine.  In October 2005, it was approved by the FDA for acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma that has not responded to or has relapsed following treatment with at least two chemotherapy regimens. It was later approved in the European Union in October 2005. It is available as a generic medication.