This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- GC-376 free acid
Commonly known or available as GC-376 - DrugBank Accession Number
- DB15796
- Background
GC-376 is a 3C-like protease (3CLpro or Mpro) inhibitor that stops the cleavage and activation of functional viral proteins required for replication and transcription in host cells1. The compound is known as a direct acting antiviral (DAA) for coronaviruses, and was initially developed using structure-guided design to combat MERS-Cov infections1,2. In addition, GC-376 displays potent activity against various coronaviruses such as feline, ferret, and mink Mpro coronavirus3,4,1,5. A prodrug of GC-373, GC-376 has recently been used to test inhibition of SARS-Cov-2 Mpro in vitro, and results show potent inhibition of this target1. These results suggest that GC-376, and its metabolites may have therapeutic potential for Covid-19.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for GC-376 free acid (DB15796)
- Weight
- Average: 485.55
Monoisotopic: 485.183186144 - Chemical Formula
- C21H31N3O8S
- Synonyms
- Not Available
- External IDs
- GC-376 free acid
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UReplicase polyprotein 1ab inhibitorSARS-CoV-2 UReplicase polyprotein 1a inhibitorSARS-CoV-2 UReplicase polyprotein 1ab inhibitorFeline coronavirus (strain FIPV WSU-79/1146) UReplicase polyprotein 1a Not Available Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012) UReplicase polyprotein 1ab Not Available 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Products
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Ingredient UNII CAS InChI Key GC-376 H1NMJ5XDG5 1416992-39-6 BSPJDKCMFIPBAW-JPBGFCRCSA-M
Categories
- Drug Categories
- Acids
- Acids, Noncarboxylic
- Alkalies
- Amides
- Amino Acids
- Amino Acids, Branched-Chain
- Amino Acids, Essential
- Amino Acids, Peptides, and Proteins
- Anions
- Carbon Compounds, Inorganic
- Carbonic Acid
- Electrolytes
- Enzyme Inhibitors
- Experimental Unapproved Treatments for COVID-19
- Ions
- Protease Inhibitors
- Sulfur Acids
- Sulfur Compounds
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- O9H5KY11SV
- CAS number
- 1417031-79-8
- InChI Key
- BSPZFJDYQHDZNR-ASPXRTSYSA-N
- InChI
- InChI=1S/C21H31N3O8S/c1-13(2)10-16(24-21(28)32-12-14-6-4-3-5-7-14)19(26)23-17(20(27)33(29,30)31)11-15-8-9-22-18(15)25/h3-7,13,15-17,20,27H,8-12H2,1-2H3,(H,22,25)(H,23,26)(H,24,28)(H,29,30,31)/t15?,16-,17-,20?/m0/s1
- IUPAC Name
- (2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-1-hydroxy-3-(2-oxopyrrolidin-3-yl)propane-1-sulfonic acid
- SMILES
- CC(C)C[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)N[C@@H](CC1CCNC1=O)C(O)S(O)(=O)=O
References
- General References
- 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]
- Galasiti Kankanamalage AC, Kim Y, Damalanka VC, Rathnayake AD, Fehr AR, Mehzabeen N, Battaile KP, Lovell S, Lushington GH, Perlman S, Chang KO, Groutas WC: Structure-guided design of potent and permeable inhibitors of MERS coronavirus 3CL protease that utilize a piperidine moiety as a novel design element. Eur J Med Chem. 2018 Apr 25;150:334-346. doi: 10.1016/j.ejmech.2018.03.004. Epub 2018 Mar 6. [Article]
- Pedersen NC, Kim Y, Liu H, Galasiti Kankanamalage AC, Eckstrand C, Groutas WC, Bannasch M, Meadows JM, Chang KO: Efficacy of a 3C-like protease inhibitor in treating various forms of acquired feline infectious peritonitis. J Feline Med Surg. 2018 Apr;20(4):378-392. doi: 10.1177/1098612X17729626. Epub 2017 Sep 13. [Article]
- 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]
- 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
- 29399539
- ChEMBL
- CHEMBL2365410
Clinical Trials
- Clinical Trials
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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 1.79 mg/mL ALOGPS logP -0.41 ALOGPS logP -0.55 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) -0.88 Chemaxon pKa (Strongest Basic) -1.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 171.13 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 117.4 m3·mol-1 Chemaxon Polarizability 48.62 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000f-7229200000-7125a68a8a4cc40af730 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-1091000000-9065b67fefac1e892945 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9834200000-1ddeeef6b074cafe52a6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-1259000000-3598d3db4c5b55bfb58d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9502100000-0647851712ac194fe10e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0c0u-7933000000-9ec18330b8e5fa6867a1 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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- 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
- 3'-5'-RNA exonuclease activity
- Gene Name
- rep
- Uniprot ID
- P0DTD1
- Uniprot Name
- Replicase polyprotein 1ab
- Molecular Weight
- 794051.285 Da
- 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 deubiquitinase activity
- Gene Name
- Not Available
- Uniprot ID
- P0DTC1
- Uniprot Name
- Replicase polyprotein 1a
- Molecular Weight
- 489984.88 Da
- 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
- 3'-5'-RNA exonuclease activity
- Gene Name
- rep
- Uniprot ID
- Q98VG9
- Uniprot Name
- Replicase polyprotein 1ab
- Molecular Weight
- 751190.21 Da
- Kind
- Protein
- Organism
- Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012)
- Pharmacological action
- Unknown
- 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 deubiquitinase activity
- Gene Name
- Not Available
- Uniprot ID
- K9N638
- Uniprot Name
- Replicase polyprotein 1a
- Molecular Weight
- 486054.32 Da
- Kind
- Protein
- Organism
- Middle East respiratory syndrome-related coronavirus (isolate United Kingdom/H123990006/2012)
- Pharmacological action
- Unknown
- 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
- 3'-5'-RNA exonuclease activity
- Gene Name
- rep
- Uniprot ID
- K9N7C7
- Uniprot Name
- Replicase polyprotein 1ab
- Molecular Weight
- 789556.615 Da
Drug created at September 03, 2020 15:32 / Updated at September 03, 2020 20:56