251010
1-β-D-Arabinofuranosylcytosine
Anticancer, antiviral agent that is especially effective against leukemias.
Synonyme(s) :
1-β-D-Arabinofuranosylcytosine, Ara-C, Cytarabine, Cytosine Arabinoside
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About This Item
Formule empirique (notation de Hill):
C9H13N3O5
Numéro CAS:
Poids moléculaire :
243.22
Numéro MDL:
Code UNSPSC :
12352200
Produits recommandés
Niveau de qualité
Pureté
≥98% (HPLC)
Forme
solid
Fabricant/nom de marque
Calbiochem®
Conditions de stockage
OK to freeze
Couleur
white
Solubilité
water: 1 mM
Conditions d'expédition
ambient
Température de stockage
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
Clé InChI
UHDGCWIWMRVCDJ-CCXZUQQUSA-N
Description générale
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.
Actions biochimiques/physiologiques
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
Avertissement
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.
Autres remarques
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.
Informations légales
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Mention d'avertissement
Warning
Mentions de danger
Conseils de prudence
Classification des risques
Repr. 2 - Skin Sens. 1
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
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