lufotrelvir   Click here for help

GtoPdb Ligand ID: 11249

Synonyms: PF-07304814 | PF07304814
PDB Ligand
Compound class: Synthetic organic
Comment: PF-07304814 is a SARS-CoV-2 3CL protease (Mpro) inhibitor from Pfizer. The structure of PF-07304814 is identical to that of the INN lufotrelvir (from proposed list 125, July 2021). PF-07304814's phosphate group (which improves solubility) is cleaved in vitro to release the active antiviral PF-00835231 [1-2]. PF-00835231 was originally developed as a SARS-CoV Mpro inhibitor in response to the 2002-2003 outbreak [3]. Like remdesivir, PF-07304814 is administered by intravenous infusion.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 6
Rotatable bonds 15
Topological polar surface area 205.96
Molecular weight 552.2
XLogP -0.17
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES COc1cccc2c1cc([nH]2)C(=O)N[C@H](C(=O)N[C@H](C(=O)COP(=O)(O)O)C[C@@H]1CCNC1=O)CC(C)C
Isomeric SMILES COc1cccc2c1cc([nH]2)C(=O)N[C@H](C(=O)N[C@H](C(=O)COP(=O)(O)O)C[C@@H]1CCNC1=O)CC(C)C
InChI InChI=1S/C24H33N4O9P/c1-13(2)9-18(28-24(32)19-11-15-16(26-19)5-4-6-21(15)36-3)23(31)27-17(10-14-7-8-25-22(14)30)20(29)12-37-38(33,34)35/h4-6,11,13-14,17-18,26H,7-10,12H2,1-3H3,(H,25,30)(H,27,31)(H,28,32)(H2,33,34,35)/t14-,17-,18-/m0/s1
InChI Key FQKALOFOWPDTED-WBAXXEDZSA-N
References
1. Baig MH, Sharma T, Ahmad I, Abohashrh M, Alam MM, Dong JJ. (2021)
Is PF-00835231 a Pan-SARS-CoV-2 Mpro Inhibitor? A Comparative Study.
Molecules, 26 (6): 1678. [PMID:33802860]
2. de Vries M, Mohamed AS, Prescott RA, Valero-Jimenez AM, Desvignes L, O'Connor R, Steppan C, Devlin JC, Ivanova E, Herrera A et al.. (2021)
A comparative analysis of SARS-CoV-2 antivirals characterizes 3CLpro inhibitor PF-00835231 as a potential new treatment for COVID-19.
J Virol, 95 (7). [PMID:33622961]
3. Hoffman RL, Kania RS, Brothers MA, Davies JF, Ferre RA, Gajiwala KS, He M, Hogan RJ, Kozminski K, Li LY et al.. (2020)
Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19.
J Med Chem, 63 (21): 12725-12747. [PMID:33054210]