cilastatin   Click here for help

GtoPdb Ligand ID: 5166

Synonyms: MK 0791 | MK-791 | MK791 | Primaxin®
Approved drug
cilastatin is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Cilastatin (sodium) is an adjunct to treatment with the antibiotic imipenem (PubChem CID 104838). Functions as a dipeptidase inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 155.02
Molecular weight 358.16
XLogP -0.52
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)C(CSCCCCC=C(C(=O)O)NC(=O)C1CC1(C)C)N
Isomeric SMILES OC(=O)[C@H](CSCCCC/C=C(/C(=O)O)\NC(=O)[C@H]1CC1(C)C)N
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
InChI Key DHSUYTOATWAVLW-WFVMDLQDSA-N
No information available.
Summary of Clinical Use Click here for help
This inhibitor of dehydropeptidase-1 is administered in fixed-dose formulations with the antibiotic imipenem in order to increase its effectiveness. Commonly used formulations are Primaxin® and Tienam®.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cilastatin inhibits dehydropeptidase-I-induced hydrolysis of the antibiotic imipenem, thereby increasing its bioactivity and prolongs its antibacterial effect. The drug also inhibits the metabolism of leukotriene D4 to leukotriene E4. It has been reported to be a bacterial beta-lactamase inhibitor [2].