favipiravir   Click here for help

GtoPdb Ligand ID: 11139

Synonyms: T-705 | T705
Approved drug
favipiravir is an approved drug (China and Japan)
Compound class: Synthetic organic
Comment: Favipiravir (T-705) is an orally delivered, guanine (purine) analogue antiviral drug (cf. remdesivir which is administered i.v.). It targets viral RNA-dependent RNA polymerase (RdRP) of RNA viruses and since the catalytic domain of RdRP is well conserved across species, has a broad-spectrum of activity; although Furuta et al. (2002) reported that actvity was weak against non-influenza virus RNA viruses [4]. Favipiravir was originally identified through a chemical library screen against influenza virus RdRP [3]. Chemically, it is a prodrug. In human cells it undergoes phosphoribosylation and phosphorylation to its active form, favipiravir-ribofuranosyl-5′-triphosphate (F-RTP). F-RTP is bound by the RdRP, but it blocks enzyme activity and so terminates chain elongation [5-6].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 88.84
Molecular weight 157.03
XLogP -0.35
No. Lipinski's rules broken 0
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Canonical SMILES Fc1c[nH]c(=O)c(n1)C(=O)N
Isomeric SMILES Fc1c[nH]c(=O)c(n1)C(=O)N
InChI InChI=1S/C5H4FN3O2/c6-2-1-8-5(11)3(9-2)4(7)10/h1H,(H2,7,10)(H,8,11)
1. Dawes BE, Kalveram B, Ikegami T, Juelich T, Smith JK, Zhang L, Park A, Lee B, Komeno T, Furuta Y et al.. (2018)
Favipiravir (T-705) protects against Nipah virus infection in the hamster model.
Sci Rep, 8 (1): 7604. [PMID:29765101]
2. Delang L, Abdelnabi R, Neyts J. (2018)
Favipiravir as a potential countermeasure against neglected and emerging RNA viruses.
Antiviral Res, 153: 85-94. [PMID:29524445]
3. Furuta Y, Komeno T, Nakamura T. (2017)
Favipiravir (T-705), a broad spectrum inhibitor of viral RNA polymerase.
Proc Jpn Acad, Ser B, Phys Biol Sci, 93 (7): 449-463. [PMID:28769016]
4. Furuta Y, Takahashi K, Fukuda Y, Kuno M, Kamiyama T, Kozaki K, Nomura N, Egawa H, Minami S, Watanabe Y et al.. (2002)
In vitro and in vivo activities of anti-influenza virus compound T-705.
Antimicrob Agents Chemother, 46 (4): 977-81. [PMID:11897578]
5. Furuta Y, Takahashi K, Kuno-Maekawa M, Sangawa H, Uehara S, Kozaki K, Nomura N, Egawa H, Shiraki K. (2005)
Mechanism of action of T-705 against influenza virus.
Antimicrob Agents Chemother, 49 (3): 981-6. [PMID:15728892]
6. Kiso M, Takahashi K, Sakai-Tagawa Y, Shinya K, Sakabe S, Le QM, Ozawa M, Furuta Y, Kawaoka Y. (2010)
T-705 (favipiravir) activity against lethal H5N1 influenza A viruses.
Proc Natl Acad Sci USA, 107 (2): 882-7. [PMID:20080770]
7. Nagata T, Lefor AK, Hasegawa M, Ishii M. (2015)
Favipiravir: a new medication for the Ebola virus disease pandemic.
Disaster Med Public Health Prep, 9 (1): 79-81. [PMID:25544306]
8. Safronetz D, Rosenke K, Westover JB, Martellaro C, Okumura A, Furuta Y, Geisbert J, Saturday G, Komeno T, Geisbert TW et al.. (2015)
The broad-spectrum antiviral favipiravir protects guinea pigs from lethal Lassa virus infection post-disease onset.
Sci Rep, 5: 14775. [PMID:26456301]