251010
Cytarabine
≥98% (HPLC), solid, DNA replication inhibito, Calbiochem
Synonym(s):
1-β-D-Arabinofuranosylcytosine, Ara-C, Cytarabine, Cytosine Arabinoside
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About This Item
Empirical Formula (Hill Notation):
C9H13N3O5
CAS Number:
Molecular Weight:
243.22
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Product Name
1-β-D-Arabinofuranosylcytosine, Anticancer, antiviral agent that is especially effective against leukemias.
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
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
Quality Level
Related Categories
Biochem/physiol Actions
Cell permeable: no
Primary Target
Anticancer, antiviral agent that is especially effective against leukemias
Anticancer, antiviral agent that is especially effective against leukemias
Product does not compete with ATP.
Reversible: no
Disclaimer
Toxicity: Harmful & Carcinogenic / Teratogenic (E)
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.
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.
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.
Preparation Note
Following reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 6 months at -70°C.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Warning
hcodes
Hazard Classifications
Repr. 2 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
Certificates of Analysis (COA)
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