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C6645

Cytosine β-D-arabinofuranoside hydrochloride

Name: Cytosine &#946;-<SC>D</SC>-arabinofuranoside hydrochloride
Brand: SIGMA

≥99% (HPLC), synthetic (inorganic), 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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About This Item

Empirical Formula (Hill Notation):

C₉H₁₃N₃O₅ · HCl

CAS Number:

69-74-9

Molecular Weight:

279.68

NACRES:

NA.77

PubChem Substance ID:

24278329

EC Number:

200-713-9

MDL number:

MFCD00012839

UNSPSC Code:

12352208

Assay:

≥99% (HPLC)

Biological source:

synthetic (inorganic)

Form:

crystalline

Solubility:

water: 50 mg/mL, clear, colorless

Storage temp.:

2-8°C

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Properties

Product Name

Cytosine β-D-arabinofuranoside hydrochloride, crystalline

biological source

synthetic (inorganic)

Quality Level

200

assay

≥99% (HPLC)

form

crystalline

mp

197-198 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

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)

Description

Application

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

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.