Other substances

2-{3-[3-Chloro-5-(cyclopropylmethoxy)phenyl]-2-oxo[2H-[1,3'-bipyridine]]-5-yl}benzonitrile

A SARS-CoV-2 3C-like protease inhibitor.

Phase of research

Potential treatment - pre-clinical evidence

How it helps

Antiviral

Drug status

Experimental

Supporting references

Contradictory references

AI-suggested references

Clinical trials

General information

2-{3-[3-Chloro-5-(cyclopropylmethoxy)phenyl]-2-oxo[2H-[1,3'-bipyridine]]-5-yl}benzonitrile is a novel non-peptide non-covalent SARS-CoV-2 3C-like protease inhibitor. It was shown to inhibit SARS-CoV-2 activity in cell culture with IC₅₀s in a range of ca. 1–2 μM with no detectable cytotoxicity at 100 μM (Zhang et al., 2021).

2-{3-[3-Chloro-5-(cyclopropylmethoxy)phenyl]-2-oxo[2H-[1,3'-bipyridine]]-5-yl}benzonitrile on PubChem

Synonyms

2-(3-(3-Chloro-5-(cyclopropylmethoxy)phenyl)-2-oxo-2H-[1,3'-bipyridin]-5-yl)benzonitrile; 2-[5-[3-chloro-5-(cyclopropylmethoxy)phenyl]-6-oxo-1-pyridin-3-ylpyridin-3-yl]benzonitrile ; XFD; 26

Structure image - 2-{3-[3-Chloro-5-(cyclopropylmethoxy)phenyl]-2-oxo[2H-[1,3'-bipyridine]]-5-yl}benzonitrile

C1CC1COC2=CC(=CC(=C2)C3=CC(=CN(C3=O)C4=CN=CC=C4)C5=CC=CC=C5C#N)Cl

Supporting references

Link	Tested on	Impact factor	Notes	Publication date
Potent Noncovalent Inhibitors of the Main Protease of SARS-CoV-2 from Molecular Sculpting of the Drug Perampanel Guided by Free Energy Perturbation Calculations Crystallization Enzyme assay In vitro In silico	in silico; in vitro enzyme assay; crystallization (parent compounds); Vero E6 cells; SARS-CoV-2	12.69	It inhibits the protease with an IC50 of ca. 0.17 μM in an enzyme assay. The compound inhibits SARS-CoV-2 infection in cell culture with IC50s in a range of ca. 1–2 μM with no detectable cytotoxicity at 100 μM.	Feb/22/2021

Clinical trials

ID	Title	Status	Phase	Start date	Completion date
NCT04895007	Comparative Evaluation of Covid-19 Vaccines Response	Recruiting		Jun/01/2021	Jun/01/2022
Alternative id - 2021-04-30T1 Interventions - Biological: Covid-19 Inactive Vaccine, recombinant human adenovirus serotype number 26, mRNA VAccine Study type - Observational Study results - No Results Available Locations - Karamanoglu Mehmetbey University, Karaman, Turkey\|Selcuk University, Konya, Turkey\|Tekirdag Namık Kemal University, Faculty of Medicine, Tekirdağ, Turkey\|Karadeniz Technic University, Faculty of Medicine, Trabzon, Turkey Study designs - Observational Model: Case-Crossover\|Time Perspective: Prospective Enrollment - 1500 Age - 18 Years to 99 Years (Adult, Older Adult) Outcome measures - Change from baseline in Anti-SARS-CoV-2 IgG Antibody and Neutralizing Antibody at 12 months
NCT04400838	Investigating a Vaccine Against COVID-19	Active, not recruiting	Phase 2\|Phase 3	May/28/2020	Mar/31/2023
Alternative id - COV002 Interventions - Biological: ChAdOx1 nCoV-19 (Abs 260)\|Biological: MenACWY vaccine\|Biological: ChAdOx1 nCoV-19 (Abs 260) + 2.2x10^10vp (qPCR) boost\|Biological: Two dose MenACWY vaccine\|Biological: ChAdOx1 nCoV-19 (qPCR)\|Biological: ChAdOx1 nCoV-19 0.5mL prime plus boost\|Biological: Two dose MenACWY vaccine min. 4 weeks apart\|Biological: Two dose ChAdOx1 nCoV-19/Covishield 0.5mL\|Biological: Two dose ChAdOx1 nCoV-19/Covishield 0.25mL & 0.5mL Study type - Interventional Study results - No Results Available Locations - University Hospital Southampton NHS Foundation Trust, Southampton, Hampshire, United Kingdom\|Castle Hill Hospital, Cottingham, Hull, United Kingdom\|St Georges University Hospital NHS Foundation Trust, London, Tooting, United Kingdom\|University Hospitals Birmingham NHS Foundation Trust, Birmingham, United Kingdom\|University Hospitals Bristol and Weston NHS Foundation Trust, Bristol, United Kingdom\|North Bristol NHS Trust, Bristol, United Kingdom\|NIHR Cambridge Clinical Research Facility, Cambridge, United Kingdom\|NHS Lothian, Western General Hospital, Edinburgh, United Kingdom\|Glasgow University and NHS Greater Glasgow & Clyde, New Lister Building, Glasgow Royal Infirmary & Queen Elizabeth University Hospital, Glasgow, United Kingdom\|Liverpool School of Tropical Medicine (LSTM), Accelerator Research Clinic. Clinical Sciences Accelerator, LIverpool, United Kingdom\|London North West University Healthcare Trust (LNWUH), Northwick Park Hospital, London, United Kingdom\|University College London Hospitals NHS Foundation Trust, London, United Kingdom\|Guy's and St Thomas' NHS Foundation Trust, Department of Infection, St Thomas Hospital, London, United Kingdom\|Imperial College Healthcare NHS Trust, London, United Kingdom\|The Newcastle upon Tyne Hospitals NHS Foundation Trust, Royal Victoria Infirmary, Newcastle upon Tyne, United Kingdom\|Public Health Wales, Newport, United Kingdom\|University of Nottingham Health Service, Cripps Health Centre, University Park, Nottingham, United Kingdom\|CCVTM, University of Oxford, Churchill Hospital, Oxford, United Kingdom\|John Radcliffe Hospital, Oxford, United Kingdom\|Sheffield Teaching Hospitals, Royal Hallamshire Hospital, Sheffield, United Kingdom Study designs - Allocation: Randomized\|Intervention Model: Sequential Assignment\|Masking: Single (Participant)\|Primary Purpose: Prevention Enrollment - 12390 Age - 18 Years and older (Adult, Older Adult) Outcome measures - Assess the efficacy of the candidate ChAdOx1 nCoV-19 against COVID-19 in adults aged 18 years and older.\|Assess the safety of the candidate vaccine ChAdOx1 nCoV-19 in adults\|Assess the safety, tolerability and reactogenicity profile of the candidate vaccine ChAdOx1 nCoV-19: occurrence of solicited local reactogenicity signs and symptoms for 7 days following\|Assess the safety, tolerability and reactogenicity profile of the candidate vaccine ChAdOx1 nCoV-19: occurrence of solicited systemic reactogenicity signs and symptoms for 7 days following\|Assess the safety, tolerability and reactogenicity profile of the candidate vaccine ChAdOx1 nCoV-19: occurrence of unsolicited adverse events (AEs) for 28 days following vaccination\|Assess the safety, tolerability and reactogenicity profile of the candidate vaccine ChAdOx1 nCoV-19 through standard blood tests (full blood count, liver and kidney function tests)\|Assess the safety, tolerability and reactogenicity profile of the candidate vaccine ChAdOx1 nCoV-19 by measuring the number of disease enhancement episodes\|Assess efficacy of the candidate ChAdOx1 nCoV-19 against severe and non-severe COVID-19: hospital admissions\|Assess efficacy of the candidate ChAdOx1 nCoV-19 against severe and non-severe COVID-19\|Assess efficacy of the candidate ChAdOx1 nCoV-19 against severe and non-severe COVID-19: number of deaths\|Assess efficacy of the candidate ChAdOx1 nCoV-19 against severe and non-severe COVID-19 by measuring seroconversion rates\|Assess efficacy of the candidate ChAdOx1 nCoV-19 against severe and non-severe COVID-19 by measuring incidence of Covid-19\|Assess humoral immunogenicity of ChAdOx1 nCoV-19: antibody quantification\|Assess humoral immunogenicity of ChAdOx1 nCoV-19: seroconversion\|Assess cellular and humoral immunogenicity of ChAdOx1 nCoV-19 through ELISpot assays (groups 1, 2, 7 and 8 only)\|Assess the safety and immunogenicity of a booster dose of ChAdOx1 nCoV-19 in older adults aged 56 years or older (two-dose schedules for groups 1, 2, 7 and 8 only): local reactogenicity\|Assess the safety and immunogenicity of a booster dose of ChAdOx1 nCoV-19 in older adults aged 56 years or older (two-dose schedules for groups 1 and 2 only): systemic reactogenicity\|Assess the safety and immunogenicity of a booster dose of ChAdOx1 nCoV-19 in older adults aged 56 years or older (two-dose schedules for groups 1 and 2 only)\|Assess the safety and immunogenicity of a booster dose of ChAdOx1 nCoV-19 in older adults aged 56 years or older (two-dose schedules for groups 1 and 2 only) through standard blood tests (full blood count, liver and kidney function tests)\|Assess the safety and immunogenicity of a booster dose of ChAdOx1 nCoV-19 in older adults aged 56 years or older (two-dose schedules for groups 1 and 2 only) via seroconversion

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