Lufotrelvir

Lufotrelvir (PF-07304814) is an antiviral drug developed by Pfizer which acts as a 3CL protease inhibitor.[1] It is a prodrug with the phosphate group being cleaved in vivo to yield the active agent PF-00835231.[2] Lufotrelvir is in human clinical trials for the treatment of COVID-19, and shows good activity against COVID-19 including several variant strains, but unlike the related drug nirmatrelvir it is not orally active and must be administered by intravenous infusion, and so has been the less favoured candidate for clinical development overall.[3][4][5]

Lufotrelvir
Legal status
Legal status
  • US: Investigational drug
Identifiers
IUPAC name
  • [(3S)-3-[(2S)-2-[(4-methoxy-1H-indol-2-yl)formamido]-4-methylpentanamido]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butoxy]phosphonic acid
CAS Number
PubChem CID
DrugBank
UNII
KEGG
ChEBI
Chemical and physical data
FormulaC24H33N4O9P
Molar mass552.521 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)COP(=O)(O)O)NC(=O)C2=CC3=C(N2)C=CC=C3OC
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
  • Key:FQKALOFOWPDTED-WBAXXEDZSA-N

See also

References
  1. Hoffman RL, Kania RS, Brothers MA, Davies JF, Ferre RA, Gajiwala KS, et al. (November 2020). "Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19". Journal of Medicinal Chemistry. 63 (21): 12725–12747. doi:10.1021/acs.jmedchem.0c01063. PMC 7571312. PMID 33054210.
  2. Boras, Britton; Jones, Rhys M.; Anson, Brandon J.; Arenson, Dan; Aschenbrenner, Lisa; Bakowski, Malina A.; Beutler, Nathan; Binder, Joseph; Chen, Emily; Eng, Heather; Hammond, Holly (2021-10-18). "Preclinical characterization of an intravenous coronavirus 3CL protease inhibitor for the potential treatment of COVID19". Nature Communications. 12 (1): 6055. Bibcode:2021NatCo..12.6055B. doi:10.1038/s41467-021-26239-2. ISSN 2041-1723. PMC 8523698. PMID 34663813.
  3. de Vries M, Mohamed AS, Prescott RA, Valero-Jimenez AM, Desvignes L, O'Connor R, et al. (February 2021). "A comparative analysis of SARS-CoV-2 antivirals characterizes 3CLpro inhibitor PF-00835231 as a potential new treatment for COVID-19". Journal of Virology. 95 (10). doi:10.1128/JVI.01819-20. PMC 8139662. PMID 33622961.
  4. Baig MH, Sharma T, Ahmad I, Abohashrh M, Alam MM, Dong JJ (March 2021). "Is PF-00835231 a Pan-SARS-CoV-2 Mpro Inhibitor? A Comparative Study". Molecules. 26 (6): 1678. doi:10.3390/molecules26061678. PMC 8002701. PMID 33802860.
  5. Vandyck K, Deval J (August 2021). "Considerations for the discovery and development of 3-chymotrypsin-like cysteine protease inhibitors targeting SARS-CoV-2 infection". Current Opinion in Virology. 49: 36–40. doi:10.1016/j.coviro.2021.04.006. PMC 8075814. PMID 34029993.
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