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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4FN3O2
Molecular Weight 157.1028
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAVIPIRAVIR

SMILES

c1c(F)nc(C(=O)N)c(n1)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

Molecular Formula C5H4FN3O2
Molecular Weight 157.1028
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.

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

1.39561914E12
PubMed

PubMed

TitleDatePubMed
Mechanism of action of T-705 against influenza virus.
2005 Mar
Treatment of late stage disease in a model of arenaviral hemorrhagic fever: T-705 efficacy and reduced toxicity suggests an alternative to ribavirin.
2008
Efficacy of orally administered T-705 pyrazine analog on lethal West Nile virus infection in rodents.
2008 Dec
Developing new antiviral agents for influenza treatment: what does the future hold?
2009 Jan 1
T-705 (favipiravir) and related compounds: Novel broad-spectrum inhibitors of RNA viral infections.
2009 Jun
Antiviral strategies for pandemic and seasonal influenza.
2010 Aug
Combination chemotherapy for influenza.
2010 Aug
[Present and future in development of new anti-influenza drugs].
2010 Sep
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:00:03 UTC 2021
Edited
by admin
on Fri Jun 25 23:00:03 UTC 2021
Record UNII
EW5GL2X7E0
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
NCI_THESAURUS C25995
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
Code System Code Type Description
CAS
259793-96-9
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
MESH
C462182
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
LACTMED
Favipiravir
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
PUBCHEM
492405
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
DRUG BANK
DB12466
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
JAPANESE REVIEW
AVIGAN
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY APPROVED MARCH 2014
FDA UNII
EW5GL2X7E0
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
INN
8916
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
NCI_THESAURUS
C81605
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
MERCK INDEX
M11863
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
DRUG CENTRAL
4887
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
ChEMBL
CHEMBL221722
Created by admin on Fri Jun 25 23:00:03 UTC 2021 , Edited by admin on Fri Jun 25 23:00:03 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
ANALOGUE->PARENT
TARGET ORGANISM->INHIBITOR
DRUG APPROVED IN CHINA FOR COVID-19. Prodrug that InhibitS the RNA-dependent RNA polymerase after activation to triphosphate.
Related Record Type Details
METABOLITE INACTIVE -> PARENT
URINE
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC IN HEALTHY JAPANESE VOLUNTEERS

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

IN HEALTHY JAPANESE VOLUNTEERS