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CHEBI:59511 - cilastatin sodium

ChEBI IDCHEBI:59511
ChEBI Namecilastatin sodium
Stars
DefinitionThe 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.
Last Modified9 January 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H25N2O5S.Na
Net Charge0
Average Mass380.442
Monoisotopic Mass380.13819
SMILESCC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)[O-])C(=O)O.[Na+]
InChIInChI=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
InChIKeyQXPBTTUOVWMPJN-QBNHLFMHSA-M
Roles Classification
Biological Roles:
protease inhibitor  A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).
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).
ChEBI Ontology
Outgoing Relation(s)
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  Source
sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoateIUPAC
sodium (Z)-7-(((R)-2-amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoateChemIDplus
(Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine monosodium saltChEBI
Manual XrefsDatabases
D02194KEGG DRUG
DB01597DrugBank
Registry NumbersSources
Beilstein:8179743Beilstein
CAS:81129-83-1ChemIDplus