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Merck
CN

A4233

Ara-G hydrate

≥98% (HPLC), solid

Synonym(s):

9-β-D-Arabinofuranosyl guanine hydrate

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O5 · xH2O
CAS Number:
38819-10-2
Molecular Weight:
283.24 (anhydrous basis)
NACRES:
NA.77
PubChem Substance ID:
329770852
UNSPSC Code:
12352200
MDL number:
MFCD00065486

Key Documents

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InChI key

NYHBQMYGNKIUIF-FJFJXFQQSA-N

SMILES string

NC1=Nc2c(ncn2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)C(=O)N1

InChI

1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1

assay

≥98% (HPLC)

form

solid

solubility

DMSO: >10 mg/mL, H2O: insoluble

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. This active form of Ara-G induces apoptosis and inhibits DNA synthesis. Ara-G is also an antineoplastic and antimetabolite.

Biochem/physiol Actions

Ara-G is an inducer of apoptosis; inhibitor of DNA synthesis; antineoplastic; and antimetabolite.
Ara-G is an inducer of apoptosis; inhibitor of DNA synthesis; antineoplastic; and antimetabolite. Ara-G 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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000131411
0000125911
0000084206
0000084207
0000106242

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Stacey L Berg et al.
Cancer chemotherapy and pharmacology, 59(6), 743-747 (2006-09-06)
Nelarabine is a water-soluble prodrug of the cytotoxic deoxyguanosine analog ara-G, to which it is rapidly converted in vivo by adenosine deaminase. Nelarabine has shown activity in the treatment of T-cell malignancies, especially T-cell acute lymphoblastic leukemia. Preliminary data suggested
Luigi Leanza et al.
Experimental cell research, 316(20), 3443-3453 (2010-07-07)
The deoxyguanosine (GdR) analog guanine-ß-d-arabinofuranoside (araG) has a specific toxicity for T lymphocytes. Also GdR is toxic for T lymphocytes, provided its degradation by purine nucleoside phosphorylase (PNP) is prevented, by genetic loss of PNP or by enzyme inhibitors. The
C Zhu et al.
FEBS letters, 474(2-3), 129-132 (2000-06-06)
The anti-leukemic nucleoside analogs 1-beta-D-arabinofuranosylcytosine (araC) and 9-beta-D-arabinofuranosylguanine (araG) are dependent on intracellular phosphorylation for pharmacological activity. AraC is efficiently phosphorylated by deoxycytidine kinase (dCK). Although araG is phosphorylated by dCK in vitro, it is a preferred substrate of mitochondrial
Sophie Curbo et al.
Reviews on recent clinical trials, 1(3), 185-192 (2008-05-14)
GW506U78 or nelarabine (Glaxo-SmithKline) is a nucleoside analog that is rapidly converted by cells of lymphoid lineage to its corresponding arabinosylguanine nucleotide triphosphate (araGTP). The triphosphate form of araG acts as a substrate for DNA polymerases and araG gets incorporated
Rie Nishi et al.
Cancer science, 104(4), 502-507 (2013-01-17)
Cytarabine (ara-C) is the key agent for treating acute myeloid leukemia. After being transported into leukemic cells, ara-C is phosphorylated, by several enzymes including deoxycytidine kinase (dCK), to ara-C triphosphate (ara-CTP), an active metabolite, and then incorporated into DNA, thereby
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