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Bemnifosbuvir

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Chemical compound

Pharmaceutical compound

Bemnifosbuvir
Clinical data

Other names	AT-527, AT-511
Legal status
Legal status	US: Investigational New Drug
Identifiers
IUPAC name Propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-[2-amino-6-(methylamino)purin-9-yl]-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
CAS Number	1998705-64-8^Y 2241337-84-6 (hemisulfate)
PubChemCID	122527455
ChemSpider	112747221
UNII	7UM3SQL968
KEGG	D12255
Chemical and physical data
Formula	C₂₄H₃₃FN₇O₇P
Molar mass	581.542 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@H](C(=O)OC(C)C)NP(=O)(OC[C@@H]1[C@H]([C@@]([C@@H](O1)N2C=NC3=C(N=C(N=C32)N)NC)(C)F)O)OC4=CC=CC=C4
InChI InChI=1S/C24H33FN7O7P/c1-13(2)37-21(34)14(3)31-40(35,39-15-9-7-6-8-10-15)36-11-16-18(33)24(4,25)22(38-16)32-12-28-17-19(27-5)29-23(26)30-20(17)32/h6-10,12-14,16,18,22,33H,11H2,1-5H3,(H,31,35)(H3,26,27,29,30)/t14-,16+,18+,22+,24+,40?/m0/s1 Key:OISLSHLAXHALQZ-HEOQURLSSA-N

Bemnifosbuvir (AT-527,RO7496998) is anantiviral drug invented byAtea Pharmaceuticals and licensed toRoche for clinical development, a novelnucleotide analog prodrug originally developed for the treatment ofhepatitis C.^[1]^[2] Bemnifosbuvir is the orally bioavailable hemisulfate salt of AT-511, which is metabolized in several steps to the active nucleotide triphosphate AT-9010, acting as anRNA polymerase inhibitor and thereby interfering with viral replication. Bemnifosbuvir has been researched for the treatment ofcoronavirus diseases such as that produced bySARS-CoV-2.^[3] It showed good results in earlyclinical trials but had inconsistent results at later stages.^[4]^[5] Bemnifosbuvir's Phase III study ended early as it failed to meet its primary endpoint of symptom alleviation and did not decrease viral load. However, the drug was well-tolerated and reduced relative hospitalization risk by 71%.^[6]

References

[edit]

^Berliba E, Bogus M, Vanhoutte F, Berghmans PJ, Good SS, Moussa A, et al. (September 2019)."Safety, pharmacokinetics and antiviral activity of AT-527, a novel purine nucleotide prodrug, in HCV-infected subjects with and without cirrhosis".Antimicrobial Agents and Chemotherapy.63 (12).doi:10.1128/AAC.01201-19.PMC 6879261.PMID 31570394.
^Good SS, Moussa A, Zhou XJ, Pietropaolo K, Sommadossi JP (2020)."Preclinical evaluation of AT-527, a novel guanosine nucleotide prodrug with potent, pan-genotypic activity against hepatitis C virus".PLOS ONE.15 (1): e0227104.Bibcode:2020PLoSO..1527104G.doi:10.1371/journal.pone.0227104.PMC 6949113.PMID 31914458.
^Good SS, Westover J, Jung KH, Zhou XJ, Moussa A, La Colla P, et al. (March 2021)."AT-527, a Double Prodrug of a Guanosine Nucleotide Analog, Is a Potent Inhibitor of SARS-CoV-2In Vitro and a Promising Oral Antiviral for Treatment of COVID-19".Antimicrobial Agents and Chemotherapy.65 (4).doi:10.1128/AAC.02479-20.PMC 8097421.PMID 33558299.
^Lowe D (19 October 2021)."AT-527 Fails a Phase II".In the Pipeline. Science.org.
^Fidler B, Gardner J (19 October 2021)."Atea, Roche change plans for oral COVID-19 drug after trial setback".Biopharmadive.com.
^Horga A, Saenz R, Yilmaz G, Simón-Campos A, Pietropaolo K, Stubbings WJ, Collinson N, Ishak L, Zrinscak B, Belanger B, Granier C, Lin K, C Hurt A, Zhou XJ, Wildum S, Hammond J (November 2023)."Oral bemnifosbuvir (AT-527) vs placebo in patients with mild-to-moderate COVID-19 in an outpatient setting (MORNINGSKY)".Future Virology.18 (13).doi:10.2217/fvl-2023-0115.PMC 10621114.PMID 37928891.

RNA virus antivirals (primarilyJ05, alsoS01AD andD06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry:Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir,Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Atilotrelvir Ensitrelvir^† Ibuzatrelvir Leritrelvir Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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