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251010 Sigma-Aldrich

1-β-D-Arabinofuranosylcytosine - CAS 147-94-4 - Calbiochem

Anticancer, antiviral agent that is especially effective against leukemias.

Synonym: 1-β-D-Arabinofuranosylcytosine - CAS 147-94-4 - Calbiochem, Ara-C, Cytarabine, Cytosine Arabinoside

  • CAS Number 147-94-4

  • Empirical Formula (Hill Notation) C9H13N3O5

  • Molecular Weight 243.22

  •  MDL number MFCD00066487

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Properties

Quality Level   100
assay   ≥98% (HPLC)
form   solid
mfr. no.   Calbiochem®
storage condition   OK to freeze
storage conditions   +2C to +8C
color   white
solubility   water: 1 mM
shipped in   ambient
InChI   1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
InChI key   UHDGCWIWMRVCDJ-CCXZUQQUSA-N

Description

General description

Anticancer, antiviral agent that is especially effective against leukemias. Induces apoptosis in human myeloid leukemia cells and in rat sympathetic neurons. Induces G1/S phase cell cycle arrest.

Cytosine analog that acts as a potent inhibitor of eukaryotic cellular and viral replicative DNA synthesis. AraCTP, formed by intracellular phosphorylation of AraC, is utilized as a substrate by DNA polymerases, which incorporate AraCMP residues into DNA. Incorporated 3′-terminal AraCMP residues inhibit further DNA synthesis by impeding chain elongation by DNA polymerase. AraC is used clinically in the treatment of various cancers, particularly leukemias and lymphomas. Also used to inhibit proliferation of cultured cells and replication of eukaryotic viruses (e.g. vaccinia virus, herpes simplex virus). Also shown to induce apoptosis in human myeloid leukemia cells and in post-mitotic rat sympathetic neurons.

Packaging

1 g in Plastic ampoule

Biochem/physiol Actions

Cell permeable: no

Primary Target
Anticancer, antiviral agent that is especially effective against leukemias

Product does not compete with ATP.

Reversible: no

Warning

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstitution

Following reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 6 months at -70°C.

Other Notes

Zarilli, R., et al. 1999. Gastroenterology 116, 1358.
Dessi, F., et al. 1995. J. Neurochem.64, 1980.
Grant, S., et al. 1994. Oncol. Res. 6, 87.
Greenberg, A.L., et al. 1994. Cancer74, 1261.
Perrino, F.W., et al. 1997. J. Biol. Chem.269, 16357.
Tomkins, C.E., et al. 1994. J. Cell Sci.107, 1499.
Taddie, J.A., and Traktman, P. 1993. J. Virol.67, 4323.
Brach, M.A., et al. 1992. Mol. Pharmacol.41, 60.
Este, E., et al. 1992. Blood79, 2246.
Owens, J.K., et al. 1992. Cancer Res.52, 2389.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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