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C1768

Sigma-Aldrich

Cytarabine

≥90% (HPLC), crystalline, DNA replication inhibitor

Synonyme(s) :

(β-D-Arabinofuranosyl)cytosine, Ara-C, Arabinocytidine, Arabinosylcytosine, Cytarabine, Cytosine arabinoside

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About This Item

Formule empirique (notation de Hill):
C9H13N3O5
Numéro CAS:
147-94-4
Poids moléculaire :
243.22
Numéro Beilstein :
89175
Numéro CE :
205-705-9
Numéro MDL:
MFCD00066487
Code UNSPSC :
12352200
ID de substance PubChem :
24892435
Nomenclature NACRES :
NA.77

product name

Cytosine β-D-arabinofuranoside, crystalline, ≥90% (HPLC)

Pureté

≥90% (HPLC)

Forme

crystalline

Température de stockage

2-8°C

Chaîne SMILES 

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

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

Informations sur le gène

human ... POLA1(5422) , POLA2(23649) , POLB(5423) , POLD1(5424) , POLD2(5425) , POLD3(10714) , POLD4(57804) , POLE(5426) , POLE2(5427) , POLE3(54107) , PRIM1(5557) , PRIM2(5558)
mouse ... Cda(72269)

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Actions biochimiques/physiologiques

Ara-C incorporates into DNA and inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation; does not inhibit RNA synthesis. Anti-leukemia agent.

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H317,H361fd

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

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Sonia G Das et al.
Journal of medicinal chemistry, 54(16), 5937-5948 (2011-07-26)
Multidrug resistance (MDR) in cancer is a phenomenon in which administration of a single chemotherapeutic agent causes cross-resistance of cancer cells to a variety of therapies even with different mechanisms of action. Development of MDR against standard therapies is a
Hamed I Ali et al.
Bioorganic & medicinal chemistry, 15(1), 242-256 (2006-10-20)
Novel 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides were prepared as a new class of antitumor agents and showed significant antitumor activities against NCI-H 460, HCT 116, A 431, CCRF-HSB-2, andKB cell lines. In vivo investigation, 2-deoxo-10-methyl-2-phenyl-5-deazaflavin exhibited the effective antitumor activity against A
M Low et al.
Internal medicine journal, 43(3), 294-297 (2012-07-05)
Although induction chemotherapy comprising high-dose cytarabine (HiDAC) in combination with idarubicin and etoposide or 'ICE' for adult acute myeloid leukaemia (AML) produces a complete remission rate of nearly 80%, gastrointestinal toxicity is significant. Omission of etoposide may produce similar clinical
Bob Löwenberg
Blood, 121(1), 26-28 (2013-01-05)
High-dose cytarabine applied during remission induction or as consolidation after attainment of a complete remission has become an established element in the treatment of adults with acute myeloid leukemia. Recent evidence has challenged the need for these exceptionally high-dose levels
Jorge Cortes et al.
The Lancet. Oncology, 14(4), 354-362 (2013-03-05)
Tosedostat is a novel oral aminopeptidase inhibitor with clinical activity in a previous phase 1-2 study in elderly patients with relapsed or refractory acute myeloid leukaemia (AML). We aimed to compare two dosing regimens of tosedostat. In this randomised phase
Afficher tous les articles scientifiques apparentés

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Nucleotide Synthesis in Cancer Cells

Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA.

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Contenu apparenté

Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

Discover Bioactive Small Molecules for Cell Cycle Research

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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