CAMOSTAT

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Search structure


Synonyms	Camostat
Status
Molecule Category	UNKNOWN
ATC	B02AB04
UNII	0FD207WKDU
EPA CompTox	DTXSID6044010


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	XASIMHXSUQUHLV-UHFFFAOYSA-N
Smiles	CN(C)C(=O)COC(=O)Cc1ccc(OC(=O)c2ccc(NC(=N)N)cc2)cc1
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H22N4O5
Molecular Weight	398.42
AlogP	1.39
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	7.0
Polar Surface Area	134.81
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	29.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay	Homo sapiens	77.0 %
Inhibition Assay: The compound was dissolved in dimethyl sulfoxide (DMSO), and diluted to an arbitrary concentration (A). A was 100-fold diluted with a buffer (0.1 M Tris (pH 8.0), 0.15 M NaCl, 10 mM CaCl2, 0.05% Brij38) (B). The r-h trypsin was diluted with a buffer to 0.088 ug/mL, and the m-trypsin was diluted with a buffer to 1/50 (C). The dilution ratio of the m-trypsin (1/50) was set to exhibit the same activity as the 0.088 ug/mL r-h trypsin as determined by kinetic analysis. The substrate solution of a substrate for the enzyme reaction, BZiPAR, (Rhodamine Reference Substrate) was diluted with a buffer to 5 umol/L (D). B; 5 uL, C; 5 uL, and D; 10 uL were added to a 384-plate, and incubated at room temperature for 30 minutes. The fluorescent signals were detected with Ex/Em = 497/520 using Tecan Safire Fluorometer. The compound was reviewed from 2500 nM to its 3-fold value, 0.0075 nM, at 12 concentrations, and the inhibitory rate of each compound was calculated.	Homo sapiens	4.6 nM
Inhibition Assay: The compound was dissolved in dimethyl sulfoxide (DMSO), and diluted to an arbitrary concentration (A). A was 100-fold diluted with a buffer (0.1 M Tris (pH 8.0), 0.15 M NaCl, 10 mM CaCl2, 0.05% Brij38) (B). The r-h trypsin was diluted with a buffer to 0.088 ug/mL, and the m-trypsin was diluted with a buffer to 1/50 (C). The dilution ratio of the m-trypsin (1/50) was set to exhibit the same activity as the 0.088 ug/mL r-h trypsin as determined by kinetic analysis. The substrate solution of a substrate for the enzyme reaction, BZiPAR, (Rhodamine Reference Substrate) was diluted with a buffer to 5 umol/L (D). B; 5 uL, C; 5 uL, and D; 10 uL were added to a 384-plate, and incubated at room temperature for 30 minutes. The fluorescent signals were detected with Ex/Em = 497/520 using Tecan Safire Fluorometer. The compound was reviewed from 2500 nM to its 3-fold value, 0.0075 nM, at 12 concentrations, and the inhibitory rate of each compound was calculated.	None	1.6 nM
Inhibition of recombinant C-terminal His10-tagged human Hepsin (R45 to L17 residues) D161E/ R162K double mutant expressed in mouse NS0 cells using Boc-QRR-AMC as substrate after 15 mins by automated fluorescence assay	Homo sapiens	29.0 nM
Inhibition of dengue virus serotype 2 His-tagged NS2B cofactor domain-NS3 protease expressed in Escherichia coli at 50 uM using 2-Abz-Nle-Lys-Arg-Arg-Ser-(3-NO2)-Tyr-NH2 as substrate preincubated with enzyme for 15 mins followed by substrate addition measured for every 1 sec for 15 mins by fluorescence plate reader based HPLC analysis relative to control	Dengue virus 2	19.6 %
Inhibition of West Nile virus His-tagged NS2B cofactor domain-NS3 protease expressed in Escherichia coli at 50 uM using 2-Abz-Gly-Leu-Lys-Arg-Gly-Gly-(3-NO2)-Tyr-NH2 as substrate preincubated with enzyme for 15 mins followed by substrate addition measured for every 1 sec for 15 mins by fluorescence microplate reader based HPLC analysis relative to control	West Nile virus	12.6 %
Inhibition of thrombin (unknown origin) at 25 uM using Boc-Val-Pro-Arg-AMC as substrate preincubated with enzyme for 15 mins followed by addition of substrate by fluorescence plate reader analysis relative to control	Homo sapiens	94.0 %
Inhibition of trypsin (unknown origin) at 50 uM using Boc-Val-Pro-Arg-AMC as substrate preincubated with enzyme for 15 mins followed by addition of substrate by fluorescence plate reader analysis relative to control	Homo sapiens	100.0 %
Inhibition of thrombin (unknown origin) using Boc-Val-Pro-Arg-AMC as substrate preincubated with enzyme for 15 mins followed by addition of substrate by fluorescence plate reader analysis	Homo sapiens	780.0 nM
Inhibition of trypsin (unknown origin) using Boc-Val-Pro-Arg-AMC as substrate preincubated with enzyme for 15 mins followed by addition of substrate by fluorescence plate reader analysis	Homo sapiens	3.5 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.53 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.13 %
Inhibition of human trypsin at 1 uM using Boc-Gln-Ala-Arg-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 60 mins by fluorescence assay relative to control	Homo sapiens	90.0 %
Inhibition of recombinant human N-terminal His-tagged HAT (Ala42 to Ile418 residues) expressed in mouse NSO cells at 1 uM using Boc-Gln-Ala-Arg-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 60 mins by fluorescence assay relative to control	Homo sapiens	90.0 %
Antiviral activity against SARS-COV 2 infected in human Calu-3 cells assessed as inhibition of viral replication at MOI of 0.01 and incubated after 2 hrs post infection for 48 hrs by direct yield reduction assay	Severe acute respiratory syndrome coronavirus 2	820.0 nM
Antiviral activity against SARS-COV 2 infected in human Calu-3 cells assessed as inhibition of viral replication at MOI of 0.01 followed by removal of test compound after cell virus adsorption incubated for 72 hrs by ENTRY-DYRA method	Severe acute respiratory syndrome coronavirus 2	40.0 nM

Cross References

Resources	Reference
ChEBI	135632
ChEMBL	CHEMBL590799
DrugBank	DB13729
DrugCentral	471
FDA SRS	0FD207WKDU
Guide to Pharmacology	6432
PubChem	2536
SureChEMBL	SCHEMBL125269
ZINC	ZINC000003871842

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).