Cilastatin
(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
Molecular Identity
Cilastatin
(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
PubChem CID: 6435415
Cilastatin is 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, 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. It has a role as a xenobiotic, a protease inhibitor, an EC 3.4.13.19 (membrane dipeptidase) inhibitor and an environmental contaminant. It is an organic sulfide, a carboxamide, a non-proteinogenic L-alpha-amino acid and a L-cysteine derivative. It is a conjugate acid of a cilastatin(1-).
2D Structure
Properties
C16H26N2O5S
Molecular Formula
358.50
Molecular Weight
g/mol
358.1562
Exact Mass
Da
-1
XLogP
Drug-like (Lipinski: < 5)
155
TPSA
May have limited oral absorption
4
H-Bond Donors
7
H-Bond Acceptors
519
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Cilastatin82009-34-5CilastatinaCilastatineCilastatinumMK-791141A6AMN38CHEBI:3697(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acidDTXSID8048238MK791MK0791(Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine2-Heptenoic acid, 7-((2-amino-2-carboxyethyl)thio)-2-(((2,2-dimethylcyclopropyl)carbonyl)amino)-, (R-(R*,S*-(Z)))-(L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid
Data from PubChem (NCBI)
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