camostat (CHEBI:135632)

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ChEBI Name	camostat

ChEBI ID	CHEBI:135632

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C20H22N4O5

Net Charge

Average Mass

398.419

Monoisotopic Mass

398.15902

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)

InChIKey

XASIMHXSUQUHLV-UHFFFAOYSA-N

SMILES

CN(C)C(=O)COC(=O)CC1=CC=C(OC(=O)C2=CC=C(NC(N)=N)C=C2)C=C1

Roles Classification
Biological Role(s):	anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. serine protease inhibitor Any protease inhibitor that restricts the action of a serine protease. antiviral agent A substance that destroys or inhibits replication of viruses.

Application(s):	antifibrinolytic drug A drug that prevent fibrinolysis or lysis of a blood clot or thrombus. anti-inflammatory agent Any compound that has anti-inflammatory effects. antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	camostat (CHEBI:135632) has functional parent 4-guanidinobenzoic acid (CHEBI:125204) camostat (CHEBI:135632) has role anti-inflammatory agent (CHEBI:67079) camostat (CHEBI:135632) has role anticoronaviral agent (CHEBI:149553) camostat (CHEBI:135632) has role antifibrinolytic drug (CHEBI:48675) camostat (CHEBI:135632) has role antihypertensive agent (CHEBI:35674) camostat (CHEBI:135632) has role antineoplastic agent (CHEBI:35610) camostat (CHEBI:135632) has role antiviral agent (CHEBI:22587) camostat (CHEBI:135632) has role serine protease inhibitor (CHEBI:64926) camostat (CHEBI:135632) is a benzoate ester (CHEBI:36054) camostat (CHEBI:135632) is a carboxylic ester (CHEBI:33308) camostat (CHEBI:135632) is a diester (CHEBI:51307) camostat (CHEBI:135632) is a guanidines (CHEBI:24436) camostat (CHEBI:135632) is a tertiary carboxamide (CHEBI:140326) camostat (CHEBI:135632) is conjugate base of camostat(1+) (CHEBI:169939)

Incoming	camostat(1+) (CHEBI:169939) is conjugate acid of camostat (CHEBI:135632)

IUPAC Name

4-{2-[2-(dimethylamino)-2-oxoethoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate

Synonyms	Sources
4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate	IUPAC
N,N-dimethylcarbamoylmethyl 4-(4-guanidinobenzoyloxy)phenylacetate	ChEBI

Registry Number	Type	Source
59721-28-7	CAS Registry Number	ChemIDplus

Last Modified

13 April 2021