Lufotrelvir

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	2468015-78-1;
PubChemCID	154699467;
DrugBank	DB16514;
UNII	XJ51YOB1SC;
KEGG	D12172;
ChEBI	CHEBI:173073;
CompTox Dashboard(EPA)	DTXSID501337108;
Chemical and physical data
Formula	C24H33N4O9P
Molar mass	552.521g·mol−1
3D model (JSmol)	Interactive image;
	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;

Lufotrelvir(PF-07304814) is anantiviraldrug developed byPfizerwhich acts as a3CL protease inhibitor.^[1]It is aprodrugwith thephosphategroup being cleavedin vivoto yield the active agentPF-00835231.^[2]Lufotrelvir is in humanclinical trialsfor the treatment ofCOVID-19,and shows good activity against COVID-19 including severalvariant strains,but unlike the related drugnirmatrelvirit is not orally active and must be administered byintravenous infusion,and so has been the less favoured candidate for clinical development overall.^[3]^[4]^[5]

References

^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.PMC7571312.PMID 33054210.
^Boras B, Jones RM, Anson BJ, Arenson D, Aschenbrenner L, Bakowski MA, et al. (October 2021)."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.PMC8523698.PMID 34663813.
^de Vries M, Mohamed AS, Prescott RA, Valero-Jimenez AM, Desvignes L, O'Connor R, et al. (March 2021)."A comparative analysis of SARS-CoV-2 antivirals characterizes 3CL^proinhibitor PF-00835231 as a potential new treatment for COVID-19 ".Journal of Virology.95(7).doi:10.1128/JVI.01819-20.PMC8139662.PMID 33622961.
^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.PMC8002701.PMID 33802860.
^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.PMC8075814.PMID 34029993.

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[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.PMC7571312.PMID 33054210.

[2] Boras B, Jones RM, Anson BJ, Arenson D, Aschenbrenner L, Bakowski MA, et al. (October 2021)."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.PMC8523698.PMID 34663813.

[3] Vries M, Mohamed AS, Prescott RA, Valero-Jimenez AM, Desvignes L, O'Connor R, et al. (March 2021)."A comparative analysis of SARS-CoV-2 antivirals characterizes 3CL^proinhibitor PF-00835231 as a potential new treatment for COVID-19 ".Journal of Virology.95(7).doi:10.1128/JVI.01819-20.PMC8139662.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.PMC8002701.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.PMC8075814.PMID 34029993.

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See also

References