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Merck
CN

855855

Cytosine β-D-arabinofuranoside hydrochloride

98%

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:
Molecular Weight:
279.68
UNSPSC Code:
12352100
MDL number:
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assay

98%

optical activity

[α]25/D +130°, c = 1 in H2O

mp

197-198 °C (lit.)

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

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.


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