Fialuridine

Product Name: Fialuridine
CAS No.: 69123-98-4
Chemical Name: Fialuridine
Synonyms: FIAU;DRG-0098;NSC 678514;FIALURIDINE;5-I-2'-F-dU;Fialuridine(FIAU);5-1-Ara-2'-F-2-dU;5-I-Ara-2'-F-2'-dU;Fluoroiodoarauracil;Fluoroiodoarauridine
CBNumber: CB4386960
Molecular Formula: C9H10FIN2O5
Formula Weight: 372.09
MOL File: 69123-98-4.mol

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Fialuridine Property

Melting point:: 216-217°C
Density: 2.18±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMSO: soluble5mg/mL, clear (warmed)
pka: 7.94±0.10(Predicted)
form: powder
color: white to beige
Merck: 14,4069
InChIKey: IPVFGAYTKQKGBM-BYPJNBLXSA-N

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Safety

Safety Statements: 24/25
WGK Germany: 3
RTECS: YQ9512500
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0632
Product name: Fialuridine
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $123
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0632
Product name: Fialuridine
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $496
Updated: 2024/03/01

TCI Chemical

Product number: D4200
Product name: 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodouracil
Purity: >98.0%(HPLC)
Packaging: 10mg
Price: $190
Updated: 2024/03/01

Cayman Chemical

Product number: 15867
Product name: Fialuridine
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 15867
Product name: Fialuridine
Purity: ≥98%
Packaging: 5mg
Price: $93
Updated: 2024/03/01

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Fialuridine Chemical Properties,Usage,Production

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.

Chemical Properties

Colourless crystals

Uses

An antiviral agent; nucleoside analog with antihepatitis B activity

Uses

Fialuridine has been used in the selection of clones.

General Description

Fialuridine (1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil, or FIAU) is an antiviral agent. It is a thymidine-based nucleoside analogue.

Biochem/physiol Actions

Fialuridine (1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil, or FIAU) and its metabolites blocks DNA polymerase at sites of multiple adjacent analog incorporation, reduces the presence of mtDNA (mitochondrial DNA) and results in mitochondrial structural defects in cultured hepatoblasts. It is considered as an efficient drug against hepatitis B virus (HBV) infection.

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.

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 [1].

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 [1].

References

[1] mansuri, m. m.,ghazzouli, i.,chen, m.s., et al. 1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-ethyluracil. a highly selective antiherpes simplex agent. journal of medicinal chemistry 30(5), 867-871 (1987).
[2] mckenzie r et al. hepatic failure and lactic acidosis due to fialuridine (fiau), an investigational nucleoside analogue for chronic hepatitis b. n engl j med. 1995 oct 26;333(17):1099-105.

Fialuridine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Fialuridine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Fialuridine 69123-98-4
Price: US $0.00-0.00/g
Min. Order: 5g
Purity: 98%min
Supply Ability: 1000g
Release date: 2021-08-30

Career Henan Chemical Co

Product: Fialuridine 69123-98-4
Price: US $5.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 1ton
Release date: 2019-08-05

69123-98-4, FialuridineRelated Search:

1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Idoxuridine 1-(2-HYDROXY-ETHOXYMETHYL)-5-IODO-1H-PYRIMIDINE-2,4-DIONE 2'-FLUORO 2'-DEOXY-5-IODOURACIL-BETA-D-ARABINOFURANOSIDE, [2-14C]- 5-IODO-2',3'-DIDEOXYURIDINE 2'-FLUORO 2'-DEOXY-5-IODOURACIL-BETA-D-ARABINOFURANOSIDE-5'-TRIPHOSPHATE Fialuridine 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil 5-Iodouracil

1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodouracil

2,4(1h,3h)-pyrimidinedione,1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-io

2’-fluoro-5-iodo-1-beta-d-arabinofuranosyluracil

2'-Deoxy-2'-fluoro-5-iodo-D-uridine

5-IODO-2'-FLUORO-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLURACIL

2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-IODO-

2'-FLUORO-5-IODOURACIL

2'-FLUORO 2'-DEOXY-5-IODOURACIL-BETA-D-ARABINOFURANOSIDE

1-(2'FLUORO-2'-DEOXYARABINOFURANOSYL)-5-IODOURACIL

1-(2-DEOXY-2-FLUORO-B-D-ARABINOFURANOSYL)-5-IODOURACIL

FIALURIDINE

FIAU

1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

5-I-Ara-2'-F-2'-dU

1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione

Fialuridine(FIAU)

5-Iodo-2'-fluoro-deoxyuridine

1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-uraci

2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-

1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodouracil 5-Iodo-2'-fluoroarauracil

Fluoroiodoarauracil

NSC 678514

1-(2-Deoxy-2-fluoro--D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione

1-(2'-Deoxy-2'-fluoro--D-arabinofuranosyl)-5-iodouracil

5-Iodo-2'-fluoroarauracil

5-Iodo-1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)uracil

2'-Deoxy-2'-fluoro-5-iodouridine

5-Iodo-2'-fluoro-2'-deoxy-ara-uridine

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-

Fialuridine FIAU 2'-Fluoro-5-iodoarauracil

5-Iodo-2'-deoxy-2'-fluoro-beta-D-arabinouridine

5-I-2'-F-dU

1-(2-Deoxy-2-fluoro--D-arabinofuranosyl)-5-iodouracil (FIAU

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil&gt

DRG-0098

5-Iodo-2’-deoxy-2’-fluoro-beta-D-arabinouridine, FIAU, Fiauridine

5-Iodo-2’-deoxy-2’-fluoro-β-D-arabinouridine

69123-98-4 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil

2'-Fluoro-5-iodoarauracil

Fialuridine USP/EP/BP

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil

1-((2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione

5-Iodo-2’-deoxy-2’-fluoro-arabinouridine

5-1-Ara-2'-F-2-dU

Fluoroiodoarauridine

Fialuridine, 10 mM in DMSO

69123-98-4

C9H10FIN2O5

Anti-virals

Bases & Related Reagents

Intermediates & Fine Chemicals

Nucleotides

Pharmaceuticals