Fialuridine

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.

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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	216-217 °C
Purity	≥95%
Density	2.18±0.1 g/cm3 (Predicted)
Solubility	Soluble in DMSO (Slightly), Methanol (Slightly)
Appearance	White to off-white solid or powder
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