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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:
147-94-4
Molecular Weight:
243.22
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00066487
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
OK to freeze
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Product Name

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

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)

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pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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