CHEBI:3697 - cilastatin

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ChEBI Name cilastatin
Definition The 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,, 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:109454, CHEBI:41538, CHEBI:143261
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Formula C16H26N2O5S
Net Charge 0
Average Mass 358.45300
Monoisotopic Mass 358.15624
InChI InChI=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
Roles Classification
Chemical Role(s): 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 (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC (membrane dipeptidase) inhibitor
An EC 3.4.13.* (dipeptidase) inhibitor that interferes with the action of membrane dipeptidase (EC
protease inhibitor
A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).
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.
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ChEBI Ontology
Outgoing cilastatin (CHEBI:3697) has role EC (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 cilastatin(1−) (CHEBI:59512) is conjugate base of cilastatin (CHEBI:3697)
(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
INNs Sources
cilastatin ChemIDplus
cilastatina ChemIDplus
cilastatine ChemIDplus
cilastatinum ChemIDplus
Synonyms Sources
(L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid ChEMBL
(Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine ChEBI
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid ChEMBL
Manual Xrefs Databases
640 DrugCentral
Cilastatin Wikipedia
DB01597 DrugBank
EP48025 Patent
EP48301 Patent
EP72014 Patent
View more database links
Registry Numbers Types Sources
6895069 Beilstein Registry Number Beilstein
6895069 Reaxys Registry Number Reaxys
82009-34-5 CAS Registry Number KEGG COMPOUND
82009-34-5 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
3495664 PubMed citation ChEMBL
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag