AntibioticMech

camostat

CHEBI:135632 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A benzoate ester resulting from the formal condensation of the carboxy group of 4-guanidinobenzoic acid with the hydroxy group of 2-(dimethylamino)-2-oxoethyl (4-hydroxyphenyl)acetate. It is a potent inhibitor of the human transmembrane protease serine 2 (TMPRSS2) and its mesylate salt is currently under investigation for its effectiveness in COVID-19 patients. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC20H22N4O5
Charge0
Average mass398.419 Da
Monoisotopic mass398.15902 Da
SourceChEBI
InChIKeyXASIMHXSUQUHLV-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)

Also called

Cross-references

Equivalent identifiers for this same structure in other resources.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
SourceNative IDLabelMinted CURIEVersion
CHEBI CHEBI:135632 camostat antibioticmech:chebi-9c6db2e7c7 2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049

Quantitative measurements
TypeReported valueAssayBindingDB IDsReference
IC50 >50000 nM DRC analysis by immunofluorescence
Ten-point DRCs were generated for each drug. Vero cells were seeded at 1.2 × 104 cells per well in DMEM, supplemented with 2% FBS and 1× antibiotic-antimycotic solution (Gibco), in black, 384-well μClear plates (Greiner Bio-One) 24 h prior to the experiment. Ten-point DRCs were generated, with compound concentrations ranging from 0.1 to 50 μM. For the viral infections, plates were transferred into the BSL3 containment facility and SARS-CoV-2 was added at a multiplicity of infection (MOI) of 0.0125. The cells were fixed at 24 hours postinfection (hpi) with 4% PFA and analyzed by immunofluorescence. The acquired images were analyzed using in-house software to quantify cell numbers and infection ratios, and antiviral activity was normalized to positive (mock) and negative (0.5% DMSO) controls in each assay plate. DRCs were fitted by sigmoidal dose-response models, with the following equation: Y = bottom + (top − bottom)/[1 + (IC50/X)Hillslope], using XLfit 4 software or Prism7. IC50 values were calculated from the normalized activity data set-fitted curves. All IC50 and 50% cytotoxic concentration (CC50) values were measured in duplicate, and the quality of each assay was controlled by Z -factor and the coefficient of variation in percent (%CV).		 RSID 874399
assay 8945_1
monomer 50031706		 PMID:32366720
EC50 11 nM Median half-maximal effective concentration (EC50) curves
Intracellular dose response (EC50 values) for selected compounds against SARS-CoV-2 were determined by pre-treating Calu-3 cells for three hr with serially diluted compounds (0.064, 0.32, 1.6, 8, 40, 200, and 1000 nM), followed by SARS-CoV-2 infection for 48 hr. Viral infection was detected by staining for dsRNA or nucleocapsid signal and quantified as described above. EC50 experiments were repeated at least three times for each compound with three technical replicates in each experiment. Intracellular nucleocapsid levels were interpolated to negative control (0.1% DMSO, no infection) = 0 and positive control (0.1% DMSO, with infection) = 100. The GraphPad Prism 9 (GraphPad Software, Inc.) nonlinear regression fit modeling variable slope was used to generate a dose-response curve [Y = Bottom + (Top-Bottom)/ (1+10^((LogIC50-X)*HillSlope)], constrained to top = 100, bottom = 0.		 RSID 1108846
assay 10287_2
monomer 50031706		 PMID:35344983
Organism-specific examples
ProteinGeneOrganismEntry
Replicase polyprotein 1ab UniProtKB:P0DTD1 — Severe acute respiratory syndrome coronavirus 2 REVIEWED

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.