251010

Cytarabine

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

• Synonyme(s) : 1-β-D-Arabinofuranosylcytosine, Ara-C, Cytarabine, Cytosine Arabinoside
• Formule empirique (notation de Hill) : C₉H₁₃N₃O₅
• Numéro CAS: 147-94-4
• Poids moléculaire : 243.22
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00066487
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Propriétés

• Nom du produit: 1-β-D-Arabinofuranosylcytosine, Anticancer, antiviral agent that is especially effective against leukemias.
• Quality Segment: 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)

Informations sur la sécurité

• pictograms: GHS08
• signalword: Danger
• hcodes: H340,H361fd
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Muta. 1B - Repr. 2
• Classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects