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Key Documents

C1768

Sigma-Aldrich

Cytarabine

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

Synonym(s):

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

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100 MG
$60.10
500 MG
$241.00
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$295.00
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100 MG
$60.10
500 MG
$241.00
1 G
$295.00
5 G
$1,040.00

About This Item

Empirical Formula (Hill Notation):
C9H13N3O5
CAS Number:
Molecular Weight:
243.22
Beilstein:
89175
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

$60.10


In StockDetails


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Product Name

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

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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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.

Features and Benefits

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.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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
Jiang-Bo Wang et al.
Cell & bioscience, 10, 98-98 (2020-08-28)
Schwann cells (SCs) play a crucial role in Wallerian degeneration after peripheral nerve injury. The expression of genes in SCs undergo a series of changes, which greatly affect the proliferation and apoptosis of SCs as well as the fate of
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

Articles

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.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Questions

1–2 of 2 Questions  
  1. Hello, does the freeze-thaw cycle affect the potency or stability of cytarabine?

    1 answer
    1. The freeze-thaw stability of this material in solution has not been determined. However, Cold Spring Harbor Protocols suggests solutions are stable for several weeks when refrigerated. For long term storage, store solutions in working aliquots at −20°C . Please see the link below to review this information:
      https://cshprotocols.cshlp.org/content/2008/12/pdb.rec11555.full?text_only=true

      Helpful?

  2. Does cytoine beta d arabinofuranoside (Arac) solution filterable by .22um filter ,, is it good idea to filter ara c

    1 answer
    1. This product is soluble in water at 50 mg/mL and may be filter sterilized. It is recommended to use a low protein binding filter membrane, such as PES, to prevent product retention in the filter. Solution stability has not been determined, however, Cold Spring Harbor protocols suggest that the filtered stock solution may be stored refrigerated or frozen.

      See the link below to review:
      https://cshprotocols.cshlp.org/content/2008/12/pdb.rec11555.full?text_only=true

      Helpful?

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