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 PF-07321332 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
  • [(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
  • 2468015-78-1
PubChem CID
DrugBank
UNII
ChEBI
Chemical and physical data
FormulaC24H33N4O9P
Molar mass552.521 g·mol−1
3D model (JSmol)
  • 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=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. 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. doi:10.1038/s41467-021-26239-2. ISSN 2041-1723.
  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. doi:10.1128/JVI.01819-20. 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). doi:10.3390/molecules26061678. 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. PMID 34029993.
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