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Key Documents

251010

Sigma-Aldrich

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
MDL number:
MFCD00066487
UNSPSC Code:
12352200
NACRES:
NA.77

product name

1-β-D-Arabinofuranosylcytosine, Anticancer, antiviral agent that is especially effective against leukemias.

Quality Level

100

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

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

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H317,H361fd

Hazard Classifications

Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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