Fialuridine
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- CAS-Nr.
- 69123-98-4
- Englisch Name:
- Fialuridine
- Synonyma:
- 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
- Summenformel:
- C9H10FIN2O5
- Molgewicht:
- 372.09
- MOL-Datei:
- 69123-98-4.mol
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Fialuridine Eigenschaften
- Schmelzpunkt:
- 216-217°C
- Dichte
- 2.18±0.1 g/cm3(Predicted)
- storage temp.
- -20°C
- Löslichkeit
- DMSO: soluble5mg/mL, clear (warmed)
- Aggregatzustand
- powder
- pka
- 7.94±0.10(Predicted)
- Farbe
- white to beige
- Merck
- 14,4069
- InChIKey
- IPVFGAYTKQKGBM-BYPJNBLXSA-N
Sicherheit
- Risiko- und Sicherheitserklärung
- Gefahreninformationscode (GHS)
S-Sätze: |
24/25 |
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WGK Germany |
3 |
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RTECS-Nr. |
YQ9512500 |
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HS Code |
29349990 |
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Bildanzeige (GHS) |
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Alarmwort |
Warnung |
Gefahrenhinweise |
Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
H302 |
Gesundheitsschädlich bei Verschlucken. |
Akute Toxizität oral |
Kategorie 4 |
Warnung |
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P264, P270, P301+P312, P330, P501 |
H315 |
Verursacht Hautreizungen. |
Hautreizung |
Kategorie 2 |
Warnung |
src="/GHS07.jpg" width="20" height="20" /> |
P264, P280, P302+P352, P321,P332+P313, P362 |
H319 |
Verursacht schwere Augenreizung. |
Schwere Augenreizung |
Kategorie 2 |
Warnung |
src="/GHS07.jpg" width="20" height="20" /> |
P264, P280, P305+P351+P338,P337+P313P |
H335 |
Kann die Atemwege reizen. |
Spezifische Zielorgan-Toxizität (einmalige Exposition) |
Kategorie 3 (Atemwegsreizung) |
Warnung |
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Sicherheit |
P261 |
Einatmen von Staub vermeiden. |
P305+P351+P338 |
BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen. |
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Fialuridine Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
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.
Chemische Eigenschaften
Colourless crystals
Verwenden
Fialuridine has been used in the selection of clones.
Allgemeine Beschreibung
Fialuridine (1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil, or FIAU) is an antiviral agent. It is a thymidine-based nucleoside analogue.
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.
Fialuridine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
D-Arabinofuranosyl bromide, 2-deoxy-2-fluoro-, 3,5-dibenzoate
3',5'-Di-O-benzoyl Fialuridine
2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate
2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil
5-BroMo-3',5'-bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine
2-(1'-Imidazoylsulfonyl)-1,3,5-tri-O-benzoyl-alpha-D-ribofuranose
Downstream Produkte
Fialuridine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
Global( 145)Lieferanten
69123-98-4()Verwandte Suche:
- 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-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-[(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-(2-Deoxy-2-fluoro--D-arabinofuranosyl)-5-iodouracil (FIAU
- 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil>
- 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
- 5-Iodo-2’-deoxy-2’-fluoro-arabinouridine
- 69123-98-4
- C9H10FIN2O5
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