bemnifosbuvir   Click here for help

GtoPdb Ligand ID: 11295

Synonyms: AT-527 | AT527 | RO-7496998 | RO7496998
Compound class: Synthetic organic
Comment: AT-527 is the orally bioavailable hemi-sulfate salt of AT-511, which is a direct-acting antiviral compound that disrupts activity of the viral RNA polymerase [1]. It was originally developed to combat hepatitis C (HCV) infection, but has been redeployed for SARS-CoV-2. Chemically AT-527 is a phosphoramidate purine nucleotide and it is metabolised to a biologically active guanosine triphosphate analogue in vivo. Preclinical results showing pan-genotype activity against HCV were published in early 2020 [2]. In October 2020 anti-SARS-CoV-2 activity was reported in preprint format [3], which converted to full peer reviewed publication in March 2021 [4].

AT-527 was developed by Atea Pharmaceuticals [5]. In October 2020 it was announced that Roche were purchasing the rights to AT-527 (and gave it the research code RO7496998) outside of the US. In the same press release, it was revealed that AT-527 would be entering Phase 3 trial in early 2021 to evaluate its efficacy as an early treatment for COVID-19 in non-hospitalised patients.

This is a complex molecule with 5 stereo-centres, so there are several CIDs with the same connectivity in PubChem. We chose to represent the molecule from CID 122527275 as it is linked to a FDA UNique Ingredient Identifier (UNII) code. This CID represents the parent molecule. For the hemi-sulfate salt structure see PubChem CID 155926085.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 194.78
Molecular weight 581.22
XLogP 2.31
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CNc1nc(N)nc2c1ncn2[C@@H]1O[C@@H]([C@H]([C@@]1(C)F)O)CO[P@@](=O)(N[C@H](C(=O)OC(C)C)C)Oc1ccccc1
Isomeric SMILES C[C@@H](C(=O)OC(C)C)N[P@](=O)(OC[C@@H]1[C@H]([C@@]([C@@H](O1)n1cnc2c(nc(nc12)N)NC)(C)F)O)Oc1ccccc1
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
InChI Key OISLSHLAXHALQZ-LZEIJKKFSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
12031 bemnifosbuvir
Synonyms Click here for help
AT-527 | AT527 | RO-7496998 | RO7496998
Database Links Click here for help
CAS Registry No. 1998705-64-8 (source: WHO INN record)
GtoPdb PubChem SID 434321730
PubChem CID 122527275
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