Cilastatin

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Cilastatin
Cilastatin.svg
Cilastatin ball-and-stick.png
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a686013
Routes of
administration
IV
ATC code J01DH51 (WHO) (combination with imipenem)
Identifiers
CAS Number 82009-34-5 YesY
PubChem (CID) 5280454
IUPHAR/BPS 5166
DrugBank DB01597 YesY
ChemSpider 4940183 YesY
UNII 141A6AMN38 YesY
KEGG D07698 YesY
ChEBI CHEBI:3697 YesY
ChEMBL CHEMBL766 YesY
ECHA InfoCard 100.072.592
Chemical and physical data
Formula C16H26N2O5S
Molar mass 358.454 g/mol
3D model (Jmol) Interactive image
  (verify)

Cilastatin is a chemical compound which inhibits the human enzyme dehydropeptidase.[1]

Dehydropeptidase is an enzyme found in the kidney and is responsible for degrading the antibiotic imipenem. Cilastatin can therefore be combined intravenously with imipenem in order to protect it from dehydropeptidase and prolong its antibacterial effect. Imipenem alone is an effective antibiotic and can be given without the cilastatin. Cilastatin itself does not have antibiotic activity although it has been proved to be active against a zinc-dependent beta-lactamase that usually confer antibiotic resistance to certain bacteria; more precisely the carbapenem family of antibiotics. This property is due to the physico-chemical similarities between membrane dipeptidase (MDP), the compound it is usually set to target, and the bacterial metallo-beta-lactamase carried by the CphA gene[1] Therefore, cilastatin is considered a beta-lactamase inhibitor, not an antibiotic per se. But as with other combinations of an antibiotic with an enzyme inhibitor, the combination allows the antibiotic to be more effective by changing the pharmacokinetics involved. Thus imipenem/cilastatin, like amoxicillin/clavulanic acid, is a commonly used combination product.

References[edit]

  1. ^ a b Keynan S, Hooper NM, Felici A, Amicosante G, Turner AJ (1995). "The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA". Antimicrob. Agents Chemother. 39 (7): 1629–31. doi:10.1128/aac.39.7.1629. PMC 162797Freely accessible. PMID 7492120.