251010

Cytarabine

≥98% (HPLC), solid, DNA replication inhibito, Calbiochem

• Synonym(s): 1-β-D-Arabinofuranosylcytosine, Ara-C, Cytarabine, Cytosine Arabinoside
• Empirical Formula (Hill Notation): C₉H₁₃N₃O₅
• CAS Number: 147-94-4
• Molecular Weight: 243.22
• MDL number: MFCD00066487
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Product Name: 1-β-D-Arabinofuranosylcytosine, Anticancer, antiviral agent that is especially effective against leukemias.
• Quality Level: 100
• description: Merck USA index - 14, 2784
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: water: 1 mM
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [n]2([c](nc(cc2)N)=O)[C@@H]1O[C@@H]([C@H]([C@@H]1O)O)CO
• 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.

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

Preparation Note

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

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H317,H361fd
• pcodes: P202 - P261 - P272 - P280 - P302 + P352 - P308 + P313
• Hazard Classifications: Repr. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3