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CHEBI:3697 - cilastatin

ChEBI IDCHEBI:3697
ChEBI Namecilastatin
Stars
DefinitionThe thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid. 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 is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products. Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4.
Secondary ChEBI IDsCHEBI:41538, CHEBI:109454, CHEBI:143261
Last Modified22 February 2017
DownloadsMolfile
FormulaC16H26N2O5S
Net Charge0
Average Mass358.460
Monoisotopic Mass358.15624
SMILESCC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O
InChIInChI=1S/C16H26N2O5S/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)/b12-6-/t10-,11+/m1/s1
InChIKeyDHSUYTOATWAVLW-WFVMDLQDSA-N
Wikipedia
Roles Classification
Chemical Roles:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
xenobiotic  A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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 (CHEBI:3697) has role EC 3.4.13.19 (membrane dipeptidase) inhibitor (CHEBI:76926)
cilastatin (CHEBI:3697) has role environmental contaminant (CHEBI:78298)
cilastatin (CHEBI:3697) has role protease inhibitor (CHEBI:37670)
cilastatin (CHEBI:3697) has role xenobiotic (CHEBI:35703)
cilastatin (CHEBI:3697) is a L-cysteine derivative (CHEBI:83824)
cilastatin (CHEBI:3697) is a carboxamide (CHEBI:37622)
cilastatin (CHEBI:3697) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
cilastatin (CHEBI:3697) is a organic sulfide (CHEBI:16385)
cilastatin (CHEBI:3697) is conjugate acid of cilastatin(1−) (CHEBI:59512)
Incoming Relation(s)
cilastatin(1−) (CHEBI:59512) is conjugate base of cilastatin (CHEBI:3697)
IUPAC Name 
(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
INNs  Source
cilastatinumChemIDplus
cilastatineChemIDplus
cilastatinaChemIDplus
cilastatinChemIDplus
Synonyms  Source
(L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acidChEMBL
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acidChEMBL
(Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteineChEBI
Manual XrefsDatabases
C01675KEGG COMPOUND
CILPDBeChem
DB01597DrugBank
D07698KEGG DRUG
EP48301Patent
EP48025Patent
EP72014Patent
CilastatinWikipedia
640DrugCentral
Registry NumbersSources
Reaxys:6895069Reaxys
CAS:82009-34-5KEGG COMPOUND
CAS:82009-34-5ChemIDplus
Citations