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
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)
Molecular Formula | C5H4FN3O2 |
Molecular Weight | 157.1026 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL612610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19428599 |
0.19 µM [EC50] | ||
Target ID: CHEMBL612765 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19428599 |
0.083 µM [EC50] | ||
Target ID: CHEMBL2366902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19428599 |
0.5 µM [EC50] | ||
Target ID: CHEMBL613845 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19428599 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AVIGAN Approved UseTreatment 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 Date1.39561914E12 |
PubMed
Title | Date | PubMed |
---|---|---|
T-705 (favipiravir) and related compounds: Novel broad-spectrum inhibitors of RNA viral infections. | 2009 Jun |
|
Inhibitors of foot and mouth disease virus targeting a novel pocket of the RNA-dependent RNA polymerase. | 2010 Dec 21 |
|
A Potent, Broad-Spectrum Antiviral Agent that Targets Viral Membranes. | 2010 May |
|
Viral replication rate regulates clinical outcome and CD8 T cell responses during highly pathogenic H5N1 influenza virus infection in mice. | 2010 Oct 7 |
|
Development of a new tacaribe arenavirus infection model and its use to explore antiviral activity of a novel aristeromycin analog. | 2010 Sep 16 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.pmda.go.jp/files/000210319.pdf
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26752302
Favipiravir inhibited Ebola replication with EC50 36.8uM
Substance Class |
Chemical
Created
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admin
on
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Thu Jul 06 21:51:53 UTC 2023
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on
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Record UNII |
EW5GL2X7E0
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Record Status |
Validated (UNII)
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C281
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NCI_THESAURUS |
C25995
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Favipiravir
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259793-96-9
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C462182
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134722
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Favipiravir
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492405
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BC-05
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DB12466
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AVIGAN
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PRIMARY | APPROVED MARCH 2014 | ||
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100000180049
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EW5GL2X7E0
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8916
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C81605
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M11863
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4887
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CHEMBL221722
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DTXSID60948878
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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ANALOGUE->PARENT | |||
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TARGET ORGANISM->INHIBITOR |
DRUG APPROVED IN CHINA FOR COVID-19. Prodrug that InhibitS the RNA-dependent RNA polymerase after activation to triphosphate.
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE ACTIVE -> PRODRUG | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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IN HEALTHY JAPANESE VOLUNTEERS |
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Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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