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
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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)
InChI Key ZCGNOVWYSGBHAU-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
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]