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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

Molecular Formula C5H4FN3O2
Molecular Weight 157.1026
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AVIGAN

PubMed

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
In Vitro Use Guide
Favipiravir inhibited Ebola replication with EC50 36.8uM
Substance Class Chemical
Record UNII
EW5GL2X7E0
Record Status Validated (UNII)
Record Version