C6645

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: 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

Properties

• 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)

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.

Other Notes

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

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H317,H319,H341,H361
• Precautionary Statements: P201 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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