Merck
All Photos(5)

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
Empirical Formula (Hill Notation):
C9H13N3O5 · HCl
CAS Number:
Molecular Weight:
279.68
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

crystalline

Quality Level

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

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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.

Packaging

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

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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