NAV

GC-373

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
GC-373
DrugBank Accession Number
DB15797
Background

GC-373 is a peptide aldehyde which is metabolized from the bisulfide adduct, GC-376 free acid1,2. It is an inhibitor of Mpro (otherwise known as 3CLpro), a viral encoded protease that cleaves and activates functional proteins involved in viral replication and transcription2. GC-373 has been shown to inhibit the Mpro target in various coronavirus strains, including feline, mink, and ferret Mpro 3. Along with its prodrug, GC-376, GC-373 was recently investigated in vitro in cell culture against SARS-Cov-2 Mpro 2. The results showed potent inhibition of the target, suggesting that GC-373 holds therapeutic potential for Covid-192.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 403.479
Monoisotopic: 403.210721046
Chemical Formula
C21H29N3O5
Synonyms
Not Available
External IDs
  • GC-373
  • GC373
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AReplicase polyprotein 1ab
inhibitor
Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012)
AReplicase polyprotein 1a
inhibitor
Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012)
UReplicase polyprotein 1ab
inhibitor
SARS-CoV-2
UReplicase polyprotein 1a
inhibitor
SARS-CoV-2
UReplicase polyprotein 1ab
inhibitor
Feline coronavirus (strain FIPV WSU-79/1146)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
W9SVW656LQ
CAS number
Not Available
InChI Key
QYENXTYKACLCGO-FQECFTEESA-N
InChI
InChI=1S/C21H29N3O5/c1-14(2)10-18(24-21(28)29-13-15-6-4-3-5-7-15)20(27)23-17(12-25)11-16-8-9-22-19(16)26/h3-7,12,14,16-18H,8-11,13H2,1-2H3,(H,22,26)(H,23,27)(H,24,28)/t16?,17-,18-/m0/s1
IUPAC Name
benzyl N-[(1S)-3-methyl-1-{[(2S)-1-oxo-3-(2-oxopyrrolidin-3-yl)propan-2-yl]carbamoyl}butyl]carbamate
SMILES
CC(C)C[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)N[C@@H](CC1CCNC1=O)C=O

References

General References
  1. Kim Y, Shivanna V, Narayanan S, Prior AM, Weerasekara S, Hua DH, Kankanamalage AC, Groutas WC, Chang KO: Broad-spectrum inhibitors against 3C-like proteases of feline coronaviruses and feline caliciviruses. J Virol. 2015 May;89(9):4942-50. doi: 10.1128/JVI.03688-14. Epub 2015 Feb 18. [Article]
  2. Vuong W, Khan MB, Fischer C, Arutyunova E, Lamer T, Shields J, Saffran HA, McKay RT, van Belkum MJ, Joyce MA, Young HS, Tyrrell DL, Vederas JC, Lemieux MJ: Feline coronavirus drug inhibits the main protease of SARS-CoV-2 and blocks virus replication. Nat Commun. 2020 Aug 27;11(1):4282. doi: 10.1038/s41467-020-18096-2. [Article]
  3. Perera KD, Galasiti Kankanamalage AC, Rathnayake AD, Honeyfield A, Groutas W, Chang KO, Kim Y: Protease inhibitors broadly effective against feline, ferret and mink coronaviruses. Antiviral Res. 2018 Dec;160:79-86. doi: 10.1016/j.antiviral.2018.10.015. Epub 2018 Oct 19. [Article]
ChemSpider
26617691
BindingDB
476983
ChEMBL
CHEMBL1821850

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP1.28Chemaxon
pKa (Strongest Acidic)12.68Chemaxon
pKa (Strongest Basic)3.13Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area113.6 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity106.58 m3·mol-1Chemaxon
Polarizability42.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udm-4191300000-6a07a86e6c59fe29d1ed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0940000000-825f40dd4db95f4e57ab
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-7921000000-69f3e8e58b9f3dccb70a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1690000000-37c47086584d5710bfbb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-ac8155d144ba65c47529
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-2910000000-fa114f39be64205284e0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Replicase polyprotein 1ab
Kind
Protein
Organism
Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012)
Pharmacological action
Yes
Actions
Inhibitor
General Function
The replicase polyprotein of coronaviruses is a multifunctional protein: it contains the activities necessary for the transcription of negative stranded RNA, leader RNA, subgenomic mRNAs and progeny virion RNA as well as proteinases responsible for the cleavage of the polyprotein into functional products.
Specific Function
Atp binding
Gene Name
rep
Uniprot ID
K9N7C7
Uniprot Name
Replicase polyprotein 1ab
Molecular Weight
789556.615 Da
Details2. Replicase polyprotein 1a
Kind
Protein
Organism
Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012)
Pharmacological action
Yes
Actions
Inhibitor
General Function
The replicase polyprotein of coronaviruses is a multifunctional protein: it contains the activities necessary for the transcription of negative stranded RNA, leader RNA, subgenomic mRNAs and progeny virion RNA as well as proteinases responsible for the cleavage of the polyprotein into functional products.
Specific Function
Cysteine-type endopeptidase activity
Gene Name
Not Available
Uniprot ID
K9N638
Uniprot Name
Replicase polyprotein 1a
Molecular Weight
486054.32 Da
Details3. Replicase polyprotein 1ab
Kind
Protein
Organism
SARS-CoV-2
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Replicase polyprotein 1ab Multifunctional protein involved in the transcription and replication of viral RNAs. Contains the proteinases responsible for the cleavages of the polyprotein.
Specific Function
Atp binding
Gene Name
rep
Uniprot ID
P0DTD1
Uniprot Name
Replicase polyprotein 1ab
Molecular Weight
794051.285 Da
Details4. Replicase polyprotein 1a
Kind
Protein
Organism
SARS-CoV-2
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Replicase polyprotein 1a Multifunctional protein involved in the transcription and replication of viral RNAs. Contains the proteinases responsible for the cleavages of the polyprotein.
Specific Function
Cysteine-type endopeptidase activity
Gene Name
Not Available
Uniprot ID
P0DTC1
Uniprot Name
Replicase polyprotein 1a
Molecular Weight
489984.88 Da
Details5. Replicase polyprotein 1ab
Kind
Protein
Organism
Feline coronavirus (strain FIPV WSU-79/1146)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
The replicase polyprotein of coronaviruses is a multifunctional protein: it contains the activities necessary for the transcription of negative stranded RNA, leader RNA, subgenomic mRNAs and progeny virion RNA as well as proteinases responsible for the cleavage of the polyprotein into functional products.
Specific Function
Atp binding
Gene Name
rep
Uniprot ID
Q98VG9
Uniprot Name
Replicase polyprotein 1ab
Molecular Weight
751190.21 Da

Drug created at September 03, 2020 15:38 / Updated at December 14, 2023 19:14