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C6645

Sigma-Aldrich

Cytosine β-D-arabinofuranoside hydrochloride

crystalline

Synonym(s):

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

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25 MG
CN¥594.52
100 MG
CN¥850.66
500 MG
CN¥2,819.14
1 G
CN¥3,828.11
5 G
CN¥16,048.99

CN¥594.52

Available to ship onApril 17, 2025Details

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25 MG
CN¥594.52
100 MG
CN¥850.66
500 MG
CN¥2,819.14
1 G
CN¥3,828.11
5 G
CN¥16,048.99

About This Item

Empirical Formula (Hill Notation):
C9H13N3O5 · HCl
CAS Number:
69-74-9
Molecular Weight:
279.68
EC Number:
200-713-9
MDL number:
MFCD00012839
UNSPSC Code:
12352202
PubChem Substance ID:
24278329
NACRES:
NA.77

CN¥594.52

Available to ship onApril 17, 2025Details

biological source

synthetic (inorganic)

Assay

≥99% (HPLC)

form

crystalline

mp

197-198 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C9H13N3O5.ClH/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);1H/t4-,6-,7+,8-;/m1./s1

InChI key

KCURWTAZOZXKSJ-JBMRGDGGSA-N

Gene Information

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

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Show Differences

1 of 4

This Item
C1768V900339M6500
Cytosine β-D-arabinofuranoside hydrochloride crystalline

C6645

Cytosine β-D-arabinofuranoside hydrochloride

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

C1768

Cytosine β-D-arabinofuranoside

Cytosine β-D-arabinofuranoside Vetec™, reagent grade, 90%

V900339

Cytosine β-D-arabinofuranoside

Cysteamine hydrochloride ≥98% (titration)

M6500

Cysteamine hydrochloride

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

300

form

crystalline

form

crystalline

form

-

form

powder or crystals

assay

≥99% (HPLC)

assay

≥90% (HPLC)

assay

90%

assay

≥98% (titration)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

mp

197-198 °C (lit.)

mp

-

mp

-

mp

67-71 °C

Application

Cytosine β-D-arabinofuranoside hydrochloride has been used in fetal bovine serum supplemented Dulbecco′s modified eagle medium (FBS-DMEM)[1] and B27/neurobasal-A medium[2] to inhibit the growth of glial cells. It has also been used to inhibit astrocyte proliferation in embryonic spinal cord neurons.[3]

Biochem/physiol Actions

Ara-C is phosphorylated to Ara-CTP and is incorporatee into DNA. It inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation, and ultimately induces apoptosis via the PKC signaling pathway. Does not inhibit RNA synthesis. Anti-leukemia agent.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H317,H319,H341,H361

Hazard Classifications

Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000438677
    0000438675
    0000438675
    0000438677
    0000435902

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    Vindhya Vijay et al.
    Leukemia research, 84, 106180-106180 (2019-07-13)
    One of the greatest challenges in treating acute myeloid leukemia (AML) is chemotherapy refractory disease. Previously, we demonstrated a novel mechanism whereby AML-induced endothelial cell (EC) activation leads to subsequent leukemia cell adherence, quiescence and chemoresistance, identifying activated ECs as
    JNK plays a key role in tau hyperphosphorylation in Alzheimer's disease models
    Ploia C, et al.
    Journal of Alzheimer'S Disease, 26(2), 315-329 (2011)
    Reduced activity of AMP-activated protein kinase protects against genetic models of motor neuron disease
    Lim MA, et al.
    The Journal of Neuroscience, 32(3), 1123-1141 (2012)
    Joost J Leenders et al.
    The Journal of biological chemistry, 285(35), 27449-27456 (2010-06-23)
    Pathological forms of left ventricular hypertrophy (LVH) often progress to heart failure. Specific transcription factors have been identified that activate the gene program to induce pathological forms of LVH. It is likely that apart from activating transcriptional inducers of LVH
    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
    View All Related Papers

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