Favipiravir

Favipiravir Struktur
259793-96-9
CAS-Nr.
259793-96-9
Englisch Name:
Favipiravir
Synonyma:
6-Fluoro-3-hydroxypyrazine-2-carboxamide;T-705;Favipiravi;6-fluoro-3,4-dihydro-3-oxo-Pyrazinecarboxamide;Avigan;Farapiwe;3-Dithian;Fapilawei;T-705,T705;3-Dithiane
CBNumber:
CB71055246
Summenformel:
C5H4FN3O2
Molgewicht:
157.1
MOL-Datei:
259793-96-9.mol

Favipiravir Eigenschaften

Schmelzpunkt:
>151°C (dec.)
Dichte
1.78±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit
Soluble in DMSO (30 mg/mL), water (12 mg/mL with warming)
Aggregatzustand
solid
pka
8.77±0.60(Predicted)
Farbe
Off-white
Stabilität:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or water may be stored at -20° for up to 3 months.
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenität Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Favipiravir Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Favipiravir, 6-fluoro-3-hydroxypyrazine-2-carboxamide, is a new broad-spectrum antiviral drug targeting RNA-dependent RNA polymerase (RdRp) developed by Japan's Toyama Chemical Pharmaceutical Company. It was approved for marketing in Japan in March 2014 for the treatment of new and recurrent influenza. During the outbreak of the new coronavirus, the results of the Phase I clinical study of the drug published in March 2020 showed that the drug may have the effect of speeding up virus clearance to alleviate the progress of new coronavirus pneumonia.

History

Favipiravir was originally developed in the late 1990s by a company that was later purchased by the Japanese firm Fujifilm as part of its transition from the photo business to healthcare. After being tested against a range of viruses, the drug was approved in Japan in 2014 for emergency use against flu epidemics or to treat new strains of influenza.

Verwenden

Favipiravir is used for the treatment of advanced Ebola virus infection in a small animal model. It suppressed the replication of Zaire Ebola virus and prevented a lethal outcome in 100% of the animals. Based on the studies, Favipiravir can be a candidate for the treatment of Ebola hemorrhagic fever. Favipiravir can be used for antiviral treatment of influenza A and B. Studies have shown that in addition to influenza virus, the drug also exhibits good antiviral activity against a variety of RNA viruses, such as Ebola virus, arena virus, Bunia virus, rabies virus and now COVID-19.

Definition

ChEBI: Favipiravir is a member of the class of pyrazines that is pyrazine substituted by aminocarbonyl, hydroxy and fluoro groups at positions 2, 3 and 6, respectively. It is an anti-viral agent that inhibits RNA-dependent RNA polymerase of several RNA viruses and is approved for the treatment of influenza in Japan. It has a role as an antiviral drug, an anticoronaviral agent and an EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor. It is a primary carboxamide, a hydroxypyrazine and an organofluorine compound.

Mechanism of action

Favipiravir is an antiviral drug that selectively inhibited the RdRP of influenza virus. It showed specific activity against all three influenza A, B, and C (Furuta et al., 2013). It also inhibited the RV replication in HeLa cells, with an EC50 of 29 μg/mL (Furuta et al., 2002). Analysis showed that the primary mechanism of action of favipiravir against the influenza virus was specific inhibition of vRNA polymerase (Furuta et al., 2005). It is predicted that a similar mechanism might occur with other viruses, such as PV and RV, inhibited by favipiravir, which may account for its broad-spectrum inhibition. Mechanistic studies show that the favipiravir and its form favipiravir-RMP (favipiravir-ribofuranosyl-50-monophosphate) do not inhibit influenza RNA polymerase activity, but it is the phosphoribosylated form, favipiravir-ribofuranosyl-50-triphosphate (RTP) that inhibits the enzyme.

Synthese

Favipiravir was synthesized in only six steps from 3-aminopyrazine-2-carboxylic acid with an overall yield of about 22.3%. Key intermediates 3 and 6 were obtained in excellent purity via recrystallization from optimized solvents, which was beneficial to large-scale production. In the key synthetic reaction, 3,6-dichloropyrazine-2-carbonitrile (6) was reacted sequentially, in one pot, with KF and 30% H2O2 to give (after crystallization from 95% EtOH) favipiravir as colorless crystals, with a 60% yield for this final step of the synthesis. (DOI:10.1007/s11696-017-0208-6)
Synthesis_259793-96-9
645 grams of sodium hydroxide were dissolved in 9L of water, the temperature was lowered to 5??C, and 1.29 kg of 6-fluoro-3-hydroxy-2-cyanopyrazine was added in batches, stirred, and heated slightly, and the temperature of the reaction system was controlled to -10??C, it takes 3.5 hours to complete the addition, after holding for 1 hour, the temperature is raised to 40??C for 1 hour. Add 100g of activated carbon to the reaction solution, hot filter, cool the mother liquor to 5??C, adjust the pH to 3-4 with concentrated hydrochloric acid, precipitate a large amount of solids, filter and dry to obtain a crude off-white powder, beaten with 2.8 liters of 15% methanol aqueous solution and filter After drying, 1.34 kg of white powder favipiravir was obtained. 1H-NMR (DMSO, 600MHz): |? 13.38 (s, 1H), 8.73 (1s, 1H), 8.51-8.49 (d, J=12, 2H) (yield 91%).

Favipiravir Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Favipiravir Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 540)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
CONIER CHEM AND PHARMA LIMITED
+8618523575427
sales@conier.com China 47465 58
Jinan Jianfeng Chemical Co., Ltd
+8615562555968
info@pharmachemm.com China 246 58
Qiuxian Baitai New Material Co., LTD
+8618330912755
sale2@hbyalin.com China 1677 58
HEBEI Meijinnong Import And Export Trade Co.,LTD
+8617363028569
admin@mjn-cn.com China 93 58
Hebei Ningnan Trade Co. LTD
+86-18034019111
admin@hbningnan.com China 278 58
Hubei Harvest Chemical CO.,Ltd
+86-13129915771 +86-15623179893
wendy@hb-harvestchem.com China 931 58
HangZhou RunYan Pharma Technology Co.,LTD.
+86-88660901 +86-18112526015
sales@runyanpharma.com China 326 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177
peter@yan-xi.com China 5990 58
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.
+86-029-86333380 18829239519
sales06@tgybio.com China 962 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971
deasea125996@gmail.com China 2504 58

259793-96-9()Verwandte Suche:


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  • 3-Dithiacyclohexane
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  • 3-Dithiane
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  • Avigan
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  • AMIDE
  • HALIDE
  • API
  • 259793-96-9
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