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SML0632

Fialuridine

Name: Fialuridine
Brand: SIGMA

≥98% (HPLC), powder, nucleoside analog

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₀FIN₂O₅

CAS Number:

69123-98-4

Molecular Weight:

372.09

UNSPSC Code:

12352200

PubChem Substance ID:

329825571

NACRES:

NA.77

MDL number:

MFCD00866922

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Fialuridine, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

F[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N2C(NC(C(I)=C2)=O)=O

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

InChI key

IPVFGAYTKQKGBM-BYPJNBLXSA-N

Related Categories

Bioactive Small Molecules

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.

Application

Fialuridine has been used in the selection of clones.

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.

Fialuridine is a nucleoside analog antiviral agent.

Fialuridine is a nucleoside analog antiviral agent. The compound displays significant mitochondrial toxicity.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000436950

0000408512

0000408510

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Mitochondrial injury. Lessons from the fialuridine trial.

P Honkoop et al.

Drug safety, 17(1), 1-7 (1997-07-01)

Fialuridine is an antiviral agent with potent activity against hepatitis B virus replication in vitro and in vivo. In a phase II study, 7 of 15 patients experienced severe toxicity due to the drug after 9 to 13 weeks of

Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B.

McKenzie R, et al.

The New England Journal of Medicine, 333(17), 1099-1105 (1995)

Fialuridine accumulates in DNA of dogs, monkeys, and rats following long-term oral administration.

Richardson FC, et al.

Proceedings of the National Academy of Sciences of the USA, 91(25), 12003-12007 (1994)

Fialuridine and its metabolites inhibit DNA polymerase gamma at sites of multiple adjacent analog incorporation, decrease mtDNA abundance, and cause mitochondrial structural defects in cultured hepatoblasts.

Lewis W, et al.

Proceedings of the National Academy of Sciences of the USA, 93(8), 3592-3597 (1996)

Mechanisms for the anti-hepatitis B virus activity and mitochondrial toxicity of fialuridine (FIAU).

J M Colacino

Antiviral research, 29(2-3), 125-139 (1996-03-01)

Fialuridine (FIAU) is a thymidine nucleoside analog with activity against various herpesviruses and hepatitis B virus (HBV) in vitro and in vivo. In a clinical evaluation for its use as a treatment for chronic HBV infection, long term (HBV) in

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Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Global Trade Item Number

SKU	GTIN
SML0632-25MG	04061832634081
SML0632-5MG	04061837101199

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