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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4FN3O2
Molecular Weight 157.1026
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAVIPIRAVIR

SMILES

NC(=O)C1=NC(F)=CNC1=O

InChI

InChIKey=ZCGNOVWYSGBHAU-UHFFFAOYSA-N
InChI=1S/C5H4FN3O2/c6-2-1-8-5(11)3(9-2)4(7)10/h1H,(H2,7,10)(H,8,11)

HIDE SMILES / InChI
Favipiravir (originally known as T-705) is an orally administered novel anti-viral compound with a unique mechanism of action that is active against a wide range of RNA-based viruses in laboratory tests. Favipiravir has recently being approved in Japan under the brand name Avigan. Avigan is an experimental antiviral drug being developed by Toyama Chemical of Japan. It is a viral RNA polymerase inhibitor with a new mechanism of action, inhibiting viral gene replication within infected cells to prevent the propagation. Favipiravir is phosphoribosylated by cellular enzymes to its active form, favipiravir-ribofuranosyl-5′- triphosphate (RTP). Favipiravir is active against a broad range of influenza viruses, including A(H1N1)pdm09, A(H5N1) and the recently emerged A(H7N9) avian virus. It also inhibits influenza strains resistant to current antiviral drugs, and shows a synergistic effect in combination with oseltamivir, thereby expanding influenza treatment options. A Phase III clinical evaluation of favipiravir for influenza therapy has been completed in Japan and two Phase II studies have been completed in the United States. In addition to its anti-influenza activity, favipiravir blocks the replication of many other RNA viruses, including arenaviruses (Junin, Machupo and Pichinde); phleboviruses (Rift Valley fever, sandfly fever and Punta Toro); hantaviruses (Maporal, Dobrava, and Prospect Hill); flaviviruses (yellow fever and West Nile); enteroviruses (polio- and rhinoviruses); an alphavirus, Western equine encephalitis virus; a paramyxovirus, respiratory syncytial virus; and noroviruses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.19 µM [EC50]
0.083 µM [EC50]
0.5 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AVIGAN

Approved Use

Treatment of novel or re-emerging pandemic influenza virus infections (limited to cases in which other influenza antiviral drugs are ineffective or not sufficiently effective).

Launch Date

2014
PubMed

PubMed

TitleDatePubMed
Treatment of late stage disease in a model of arenaviral hemorrhagic fever: T-705 efficacy and reduced toxicity suggests an alternative to ribavirin.
2008
Intracellular metabolism of favipiravir (T-705) in uninfected and influenza A (H5N1) virus-infected cells.
2009 Oct
Antiviral strategies for pandemic and seasonal influenza.
2010 Aug
Patents

Sample Use Guides

In Vivo Use Guide
The usual adult dosage is 1600 mg of favipiravir administered orally twice daily on Day 1, followed by 600 mg orally twice daily from Day 2 to Day 5. The total treatment duration should be 5 days.
Route of Administration: Oral
Favipiravir inhibited Ebola replication with EC50 36.8uM
Name Type Language
FAVIPIRAVIR
INN   JAN   USAN   WHO-DD  
INN   USAN  
Official Name English
AVIGAN
Brand Name English
6-Fluoro-3-hydroxypyrazine-2-carboxamide
Systematic Name English
FAVIPIRAVIR [USAN]
Common Name English
FAVIPIRAVIR [JAN]
Common Name English
FAVIPIRAVIR [MI]
Common Name English
Favipiravir [WHO-DD]
Common Name English
2-PYRAZINECARBOXAMIDE, 6-FLUORO-3,4-DIHYDRO-3-OXO-
Systematic Name English
T-705
Code English
favipiravir [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
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NCI_THESAURUS C25995
Created by admin on Sat Dec 16 16:22:06 GMT 2023 , Edited by admin on Sat Dec 16 16:22:06 GMT 2023
Code System Code Type Description
WIKIPEDIA
Favipiravir
Created by admin on Sat Dec 16 16:22:06 GMT 2023 , Edited by admin on Sat Dec 16 16:22:06 GMT 2023
PRIMARY
CAS
259793-96-9
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MESH
C462182
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PRIMARY
CHEBI
134722
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LACTMED
Favipiravir
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PUBCHEM
492405
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USAN
BC-05
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DRUG BANK
DB12466
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JAPANESE REVIEW
AVIGAN
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PRIMARY APPROVED MARCH 2014
SMS_ID
100000180049
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FDA UNII
EW5GL2X7E0
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INN
8916
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NCI_THESAURUS
C81605
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MERCK INDEX
m11863
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DRUG CENTRAL
4887
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ChEMBL
CHEMBL221722
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EPA CompTox
DTXSID60948878
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PRIMARY