Fialuridine

Base Information Edit

Chemical Name:Fialuridine
CAS No.:69123-98-4
Molecular Formula:C9H10FIN2O5
Molecular Weight:372.092
Hs Code.:29349990
European Community (EC) Number:688-476-1
UNII:53T7IN77LC
DSSTox Substance ID:DTXSID701028030
Nikkaji Number:J61.759H
Wikipedia:Fialuridine
Wikidata:Q5446286
NCI Thesaurus Code:C73197
Metabolomics Workbench ID:155487
ChEMBL ID:CHEMBL271475
Mol file:69123-98-4.mol

Synonyms:1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil;1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione;1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodo-unracil;123I-FIAU;2'-fluoro-5-iodoarauracil;fialuridine;FIAU

Suppliers and Price of Fialuridine

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Fialuridine
10mg
$ 446.00

TCI Chemical
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodouracil >98.0%(HPLC)
10mg
$ 172.00

Sigma-Aldrich
Fialuridine ≥98% (HPLC)
5mg
$ 103.00

Sigma-Aldrich
Fialuridine ≥98% (HPLC)
25mg
$ 415.00

Medical Isotopes, Inc.
1-(2-Deoxy-2-fluoro-?-D-arabinofuranosyl)-5-iodouracil
5 mg
$ 995.00

Medical Isotopes, Inc.
1-(2-Deoxy-2-fluoro-?-D-arabinofuranosyl)-5-iodouracil
1 mg
$ 685.00

Crysdot
1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodouracil 95+%
1g
$ 450.00

Chem-Impex
Fialuridine,≥98%(HPLC) ≥98%(HPLC)
10MG
$ 195.69

Cayman Chemical
Fialuridine ≥98%
25mg
$ 312.00

Cayman Chemical
Fialuridine ≥98%
1mg
$ 28.00

Total 51 raw suppliers

Chemical Property of Fialuridine Edit

Chemical Property:

Appearance/Colour:Colourless crystals
Melting Point:216-217°C
Refractive Index:1.685
PKA:7.94±0.10(Predicted)
PSA：104.55000
Density:2.18 g/cm³
LogP:-1.27010
Storage Temp.:Refrigerator
Solubility.:DMSO: soluble5mg/mL, clear (warmed)
XLogP3:-0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:371.96185
Heavy Atom Count:18
Complexity:418

Purity/Quality:

98%min ^*data from raw suppliers

Fialuridine ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:
Safety Statements: 24/25

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)F)I
Isomeric SMILES:C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I
Recent ClinicalTrials:The Tolerance of HIV-Infected Patients With Herpes Group Virus Infections to Oral Doses of FIAU
Description Fialuridine (FIAU) is one of a series of 2'-fluoro-substituted arabinosyl pyrimidine nucleosides that have demonstrated potent antiviral activities against a number of clinically important viruses, including hepatitis B virus (HBV). Analogs of FIAU have been shown to inhibit viral replication in the woodchuck and duck models of HBV infection. Although the mechanism of the anti-HBV activity is not well understood, evidence suggests that the triphosphate analog of FIAU is a potent inhibitor of HBV DNA polymerase activity. During early clinical investigation FIAU showed much promise as an antiHBV drug because it markedly reduced the level of HBV DNA in the serum of patients with chronic hepatitis B. However, clinical trials were terminated after adverse events occurred following oral administration of FIAU (0.1 and 0.25 mg/kg of body weight per day) for more than 2 months. The mechanism of the unexpected delayed toxicity is unresolved.
Uses An antiviral agent; nucleoside analog with antihepatitis B activity Fialuridine has been used in the selection of clones.
Clinical Use Fialuridine, a nucleoside analog designed for the treatment of hepatitis B virus infection, failed in clinical trials due to fatal hepatotoxicity, occuring after 13 weeks of 0.25 mg/kg qd dosing in HBV infected patients. Both in vitro assays as well as preclinical in vivo tests in mice, rats, dogs, and primates could not predict its hepatotoxic potential. Fialuridine toxicity is thought to be mediated by human-specific impaired mitochondrial function after long-term exposure. We used the micropatterned primary hepatocyte coculture model, HepatoPac?, to assess fialuridine-mediated toxicity in vitro. To confirm the human specific toxicity, also rat, dog and monkey HepatoPac? were exposed to fialuridine. Another nucleoside analog, sofosbuvir, which is on the market for the treatment of hepatitis C virus infection and shows no signs of hepatotoxicity in the clinic, was used to study whether this approach would be able to distinguish a nucleoside analog with clinical chronic DILI finding from a nucleoside analog without DILI findings.

Technology Process of Fialuridine

There total 11 articles about Fialuridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.8%

: 97614-45-4
5-iodo-1-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)uracil

: 69123-98-4
fialuridine

Guidance literature:: 5-iodo-1-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)uracil; With water; sodium hydroxide; In tetrahydrofuran; for 4h;

Acidic conditions;