camostat   Click here for help

GtoPdb Ligand ID: 6432

Synonyms: ONO-3403
Approved drug
camostat is an approved drug
Compound class: Synthetic organic
Comment: Publications and data are also linked to the camostat mesilate salt (PubChem CID 5284360). There is an active metabolite reported as FOY 251 but this also maps to the mesylate salt (PubChem CID 130394), with the parent compound being PubChem CID 130395

SARS-CoV-2 and COVID-19: Inhibition of TMPRSS2 partially blocks entry of SARS-CoV-2 into Caco-2 cells [1], a result which indicates an opportunity for repurposing this already approved drug for COVID-19. Complete blockade of SARS-CoV-2 entry can be achieved by combined inhibition of TMPRSS2 (by camostat) and the endosomal cysteine proteases cathepsins B and L (by aloxistatin; E-64d). In August 2020 Edinburgh University, the CRUK's Centre for Drug Development and Latus Therapeutics began the Phase 2/3 SPIKE-1 trial (NCT04455815) of camostat in non-hospitalised CoV-2 positive patients, to determine if the drug can reduce the progression of COVID-19 symptoms- access CRUK's trial webpage here.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 137.31
Molecular weight 398.16
XLogP 1.17
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN(C(=O)COC(=O)Cc1ccc(cc1)OC(=O)c1ccc(cc1)N=C(N)N)C
Isomeric SMILES CN(C(=O)COC(=O)Cc1ccc(cc1)OC(=O)c1ccc(cc1)N=C(N)N)C
InChI InChI=1S/C20H22N4O5/c1-24(2)17(25)12-28-18(26)11-13-3-9-16(10-4-13)29-19(27)14-5-7-15(8-6-14)23-20(21)22/h3-10H,11-12H2,1-2H3,(H4,21,22,23)
InChI Key XASIMHXSUQUHLV-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
[4-[2-(2-dimethylamino-2-oxoethoxy)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate
International Nonproprietary Names Click here for help
INN number INN
5068 camostat
Synonyms Click here for help
ONO-3403
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678726
Reactome Reaction Reactome logo R-HSA-9681514
Other databases
CAS Registry No. 59721-28-7
ChEMBL Ligand CHEMBL590799
DrugCentral Ligand 471
GtoPdb PubChem SID 178103048
PubChem CID 2536
Search Google for chemical match using the InChIKey XASIMHXSUQUHLV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XASIMHXSUQUHLV
Search PubMed clinical trials camostat
Search PubMed titles camostat
Search PubMed titles/abstracts camostat
UniChem Compound Search for chemical match using the InChIKey XASIMHXSUQUHLV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XASIMHXSUQUHLV-UHFFFAOYSA-N
Wikipedia Camostat