251010
Cytarabine
≥98% (HPLC), solid, DNA replication inhibito, Calbiochem
Synonyme(s) :
1-β-D-Arabinofuranosylcytosine, Ara-C, Cytarabine, Cytosine Arabinoside
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A propos de cet article
Formule empirique (notation de Hill) :
C9H13N3O5
Numéro CAS:
Poids moléculaire :
243.22
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Service technique
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1-β-D-Arabinofuranosylcytosine, Anticancer, antiviral agent that is especially effective against leukemias.
Quality Level
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
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.
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)
signalword
Danger
hcodes
Hazard Classifications
Muta. 1B - Repr. 2
Classe de stockage
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
Certificats d'analyse (COA)
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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.
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Ryan Reshke et al.
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A small percentage of the short interfering RNA (siRNA) delivered via passive lipid nanoparticles and other delivery vehicles reaches the cytoplasm of cells. The high doses of siRNA and delivery vehicle that are thus required to achieve therapeutic outcomes can
Candice Kutchukian et al.
The EMBO journal, 40(13), e105990-e105990 (2021-05-22)
Cholesterol and phosphoinositides (PI) are two critically important lipids that are found in cellular membranes and dysregulated in many disorders. Therefore, uncovering molecular pathways connecting these essential lipids may offer new therapeutic insights. We report that loss of function of
Numéro d'article de commerce international
| Référence | GTIN |
|---|---|
| 251010-1GM | 04055977199192 |