D5782

2′,3′-Dideoxycytidine

≥98% (HPLC)

• Synonym(s): ddC
• Empirical Formula (Hill Notation): C₉H₁₃N₃O₃
• CAS Number: 7481-89-2
• Molecular Weight: 211.22
• Beilstein/REAXYS Number: 654956
• MDL number: MFCD00012188
• UNSPSC Code: 41106305
• PubChem Substance ID: 24278377
• NACRES: NA.52

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• assay: ≥98% (HPLC)
• form: powder
• color: colorless
• mp: 217-218 °C (lit.)
• solubility: water: 50 mg/mL, clear, colorless to faintly yellow
• storage temp.: −20°C
• SMILES string: NC1=NC(=O)N(C=C1)[C@H]2CC[C@@H](CO)O2
• InChI: 1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1
• InChI key: WREGKURFCTUGRC-POYBYMJQSA-N

Description

Application

2′,3′-Dideoxycytidine is used:

• as a DNA chain-terminating nucleotide for DNA sequencing methods based on the Sanger chain-termination method
• as a nucleoside reverse transcriptase inhibitor (NRTI) to study its effects on the development of mechanical allodynia in aging mice
• as a mitochondrial DNA (mtDNA) replication inhibitor to inhibit the activation of cGAS-STING pathway and study its effects on signaling protein-stimulator of interferon genes (STING), cyclic GMP-AMP synthase (cGAS), and phospho-interferon regulator factor 3 (p-IRF3) expression in mouse hippocampal and microglial cells
• as an NRTI inhibitor to study its effects on the drug induced-mitochondrial toxicity in Caenorhabditis elegans

Biochem/physiol Actions

2′,3′-Dideoxycytidine (ddC), is an ionic compound and a nucleoside analog. It acts as a nucleoside reverse transcriptase inhibitor and exhibits therapeutic effects against human immunodeficiency virus (HIV) infection. 2′,3′-Dideoxycytidine possesses anti-adenovirus activity and inhibits the adenovirus polymerase.

Safety Information

• pictograms: GHS08
• signalword: Warning
• hcodes: H351
• pcodes: P281
• Hazard Classifications: Carc. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges