C6645

Cytosine β-D-arabinofuranoside hydrochloride

≥99% (HPLC), synthetic (inorganic), crystalline

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

Properties

• Product Name: Cytosine β-D-arabinofuranoside hydrochloride, crystalline
• biological source: synthetic (inorganic)
• Quality Segment: 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.

Other Notes

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

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H317,H319,H341,H361
• pcodes: P201 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable