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Antiviral API
- Arenavirus
- Cytomegalovirus (CMV)
- Endogenous Metabolite
- Enterovirus (EV)
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- HIV Integrase
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- Human immunodeficiency Virus (HIV)
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- Orthopoxvirus
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- Antiviral intermediates
Fialuridine
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| Category | Orthopoxvirus |
| CAS | 69123-98-4 |
| Description | Fialuridine (FIAU) is a thymidine-based nucleoside analog with antiviral activity. Fialuridine and its metabolites blocks DNA synthesis in human cytomegalovirus and hepatitis B, as well as herpes simplex. |
Product Information
| Synonyms | 5-Iodo-2'-deoxy-2'-fluoro-beta-D-arabinouridine; FIAU; Fluoroiodoarauracil; 5-Iodo-2'-Fluoroarauracil; NSC 678514; 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione; 1-(2'-Deoxy-2'-fluoro-β-D-arabinofuranosyl)-5-iodouracil |
| IUPAC Name | 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione |
| Molecular Weight | 372.09 |
| Molecular Formula | C9H10FIN2O5 |
| Canonical SMILES | C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)F)I |
| InChI | InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1 |
| InChIKey | IPVFGAYTKQKGBM-BYPJNBLXSA-N |
| Melting Point | >202°C (dec.) |
| Purity | ≥95% |
| Density | 2.18±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol (Slightly) |
| Appearance | Crystalline Solid |
| Application | Antiviral Agents |
| Storage | Store at 2-8°C |
| Complexity | 418 |
| Exact Mass | 371.96185 |
| Index Of Refraction | 1.685 |
| In Vitro | Previous in-vitro data showed that 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil (FEAU) had activity against herpes simplex virus types 1 and 2 comparable to that of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyluracil (FMAU), fialuridine (FIAU), and acyclovir (ACV). The cellular toxicity of FEAU was found to be much lower than that of FIAU. Biochemical experiments indicated that FEAU had similar affinity toward thymidine kinases encoded by HSV 1 and 2 and a much lower affinity for cellular thymidine kinase than thymidine. |
| In Vivo | The in-vivo antiviral efficiency of FEAU was compared with that of FIAU and ACV by using the herpes encephalitis mode. Moreover, ACV and FEAU could significantly increase the number of survivors at doses of 50 and 100 mg/kg per day, respectively, and FIAU showed significant activity at 25 mg/kg per day in the animal model. |
| PSA | 104.55000 |
| Target | DNA/RNA Synthesis; Orthopoxvirus |
| XLogP3-AA | -0.9 |
