C1768

Sigma-Aldrich

Cytosine β-D-arabinofuranoside

crystalline, ≥90% (HPLC)

Synonym(s):
(β-D-Arabinofuranosyl)cytosine, Cytarabine, Arabinosylcytosine, Cytosine arabinoside, Ara-C, Arabinocytidine
Empirical Formula (Hill Notation):
C9H13N3O5
CAS Number:
Molecular Weight:
243.22
Beilstein/REAXYS Number:
89175
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥90% (HPLC)

form

crystalline

storage temp.

2-8°C

SMILES string

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

InChI key

UHDGCWIWMRVCDJ-CCXZUQQUSA-N

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Packaging

100, 500 mg in poly bottle
1, 5 g in poly bottle

Biochem/physiol Actions

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

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...
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...
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...
Alberto Diez-Torrubia et al.
Journal of medicinal chemistry, 53(2), 559-572 (2009-12-17)
Here we explore the applicability of the dipeptidyl peptidase IV (DPPIV/CD26) based prodrug approach to a variety of amine-containing drugs. Efficient procedures have been developed for the synthesis of dipeptide and tetrapeptide amide prodrugs including N-acylation protocols of the exocyclic...
Sergio Amadori et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(35), 4424-4430 (2013-10-16)
This randomized trial evaluated the efficacy and toxicity of sequential gemtuzumab ozogamicin (GO) and standard chemotherapy in older patients with newly diagnosed acute myeloid leukemia (AML). Patients (n = 472) age 61 to 75 years were randomly assigned to induction...
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