1H-Indole-2-carboxamide, N-[(1S)-1-[[[(1S)-3-hydroxy-2-oxo-1-[[(3S)-2-oxo-3-pyrrolidinyl]methyl]propyl]amino]carbonyl]-3-methylbutyl]-4-methoxy- (9CI)

1H-Indole-2-carboxamide, N-[(1S)-1-[[[(1S)-3-hydroxy-2-oxo-1-[[(3S)-2-oxo-3-pyrrolidinyl]methyl]propyl]amino]carbonyl]-3-methylbutyl]-4-methoxy- (9CI) Property

Boiling point:

865.8±65.0 °C(Predicted)

Density 

1.264±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMSO : 250 mg/mL (529.07 mM; Need ultrasonic)

form 

A solid

pka

12.76±0.10(Predicted)

color 

White to off-white

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

1H-Indole-2-carboxamide, N-[(1S)-1-[[[(1S)-3-hydroxy-2-oxo-1-[[(3S)-2-oxo-3-pyrrolidinyl]methyl]propyl]amino]carbonyl]-3-methylbutyl]-4-methoxy- (9CI) Chemical Properties,Usage,Production

Uses

PF-00835231 is a CoV-2 cysteine 3C-like protease (3CLpro) inhibitor, with IC50s of 0.27 nM and 4 nM for SARS CoV-2 and SARS CoV-1 3CLpro, respectively. PF-00835231 is developed for the research of anti-SARS-CoV-2/COVID-19. PF-00835231 can inhibit cell infections and also suppress infections in animal models[1][2][3].

Definition

ChEBI: PF-00835231 is a primary alcohol resulting from the cleavage of the phosphate group of the prodrug PF-07304814. It is an inhibitor of SARS-CoV-1 and -2 main protease (3CLpro) and exhibits potent in vitro antiviral activity. It has a role as an anticoronaviral agent, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor and a drug metabolite. It is an aromatic ether, a L-leucine derivative, an indolecarboxamide, a member of pyrrolidin-2-ones, a secondary carboxamide and a primary alcohol.

Biological Activity

Potent and selective corona virus hCoV, SARS CoV-1 & CoV-2 main protease (Mpro; 3CLpro) substrate site Cys145 covalent inhibitor with low host cytotoxicity.

in vivo

IC 50

HIV-1; HRV3C: 2.79 μM (IC₅₀)

References

[1] Robert L Hoffman, et al. Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19. J Med Chem. 2020 Nov 12;63(21):12725-12747. DOI:10.1021/acs.jmedchem.0c01063
[2] de Vries M, et al. A comparative analysis of SARS-CoV-2 antivirals in human airway models characterizes 3CLpro inhibitor PF-00835231 as a potential new treatment for COVID-19. bioRxiv [Preprint]. 2021 Feb 19:2020.08.28.272880. DOI:10.1101/2020.08.28.272880
[3] Wujun Chen, wt al. Review of preclinical data of PF-07304814 and its active metabolite derivatives against SARS-CoV-2 infection. Front Pharmacol. 2022 Nov 11:13:1035969. DOI:10.3389/fphar.2022.1035969