GC-373

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 acid^1,2. It is an inhibitor of M^pro (otherwise known as 3CL^pro), a viral encoded protease that cleaves and activates functional proteins involved in viral replication and transcription². GC-373 has been shown to inhibit the M^pro target in various coronavirus strains, including feline, mink, and ferret M^{pro 3}. Along with its prodrug, GC-376, GC-373 was recently investigated in vitro in cell culture against SARS-Cov-2 M^{pro 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

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for GC-373 (DB15797)

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Weight

Average: 403.479
Monoisotopic: 403.210721046

Chemical Formula

C₂₁H₂₉N₃O₅

Synonyms

Not Available

External IDs

• GC-373
• GC373

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
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)
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)

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

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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

• Experimental Unapproved Treatments for COVID-19

Classification

Not classified

Affected organisms

Not Available

Chemical Identifiers

UNII

Not Available

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]

External Links

ChemSpider

26617691

ChEMBL

CHEMBL1821850

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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

Property	Value	Source
Water Solubility	0.0386 mg/mL	ALOGPS
logP	1.04	ALOGPS
logP	1.28	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.6 Å2	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	106.58 m3·mol-1	ChemAxon
Polarizability	42.97 Å3	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Targets

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Details1. 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

Details2. 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

Details3. 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

Details4. 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

Details5. 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

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Drug created on September 03, 2020 15:38 / Updated on September 03, 2020 20:54