CHEBI:59511 - cilastatin sodium

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ChEBI Name cilastatin sodium
ChEBI ID CHEBI:59511
Definition The monosodium salt of cilastatin. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin sodium is therefore administered with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to microbiologically inactive and potentially nephrotoxic products.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H25N2NaO5S
Net Charge 0
Average Mass 380.43500
Monoisotopic Mass 380.13819
InChI InChI=1S/C16H26N2O5S.Na/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21;/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23);/q;+1/p-1/b12-6-;/t10-,11+;/m1./s1
InChIKey QXPBTTUOVWMPJN-QBNHLFMHSA-M
SMILES [Na+].CC1(C)C[C@@H]1C(=O)N\C(C(O)=O)=C/CCCCSC[C@H](N)C([O-])=O
Roles Classification
Biological Role(s): EC 3.4.13.19 (membrane dipeptidase) inhibitor
An EC 3.4.13.* (dipeptidase) inhibitor that interferes with the action of membrane dipeptidase (EC 3.4.13.19).
protease inhibitor
A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cilastatin sodium (CHEBI:59511) has part cilastatin(1−) (CHEBI:59512)
cilastatin sodium (CHEBI:59511) has role EC 3.4.13.19 (membrane dipeptidase) inhibitor (CHEBI:76926)
cilastatin sodium (CHEBI:59511) has role protease inhibitor (CHEBI:37670)
cilastatin sodium (CHEBI:59511) is a organic sodium salt (CHEBI:38700)
IUPAC Name
sodium (2R)-2-amino-3-{[(5Z)-6-carboxy-6-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hex-5-en-1-yl]sulfanyl}propanoate
Synonyms Sources
(Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine monosodium salt ChEBI
sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoate IUPAC
sodium (Z)-7-(((R)-2-amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate ChemIDplus
Manual Xrefs Databases
D02194 KEGG DRUG
DB01597 DrugBank
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Registry Numbers Types Sources
81129-83-1 CAS Registry Number ChemIDplus
8179743 Beilstein Registry Number Beilstein
Last Modified
09 January 2014