• USA Home
  • C6645 - Cytosine β-D-arabinofuranoside hydrochloride

EMAIL THIS PAGE TO A FRIEND
C6645 Sigma-Aldrich

Cytosine β-D-arabinofuranoside hydrochloride

crystalline

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

  • CAS Number 69-74-9

  • Empirical Formula (Hill Notation) C9H13N3O5 · HCl

  • Molecular Weight 279.68

  •  EC Number 200-713-9

  •  MDL number MFCD00012839

  •  PubChem Substance ID 24278329

  •  NACRES NA.77

Purchase

Properties

Related Categories Antitumor Agents, Apoptosis and Cell Cycle, Cancer Research, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
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.

Packaging

1, 5 g in glass bottle

100, 500 mg in glass bottle

25 mg in poly 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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number
Protocols & Articles

Articles

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
Keywords: AGE, Alkylations, Apoptosis, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Degradations, Eliminations, Environmental, Enzymology, Gene expression, Genetic, Infrared spectroscopy, Metabolites, Methylations, Mutagens, Oncology, Oxidations, Polymorphisms, Rearrangements, Recombination, Substitutions, Transcription, transformation

Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?