Cilastatin

Cilastatin

Systematic (IUPAC) name
(Z)-7-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanyl-2-{[(1S)- 2,2-dimethylcyclopropanecarbonyl]amino}hept-2-enoic acid
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a686013
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	82009-34-5 Y
ATC code	?
PubChem	CID 5280454
DrugBank	EXPT00918
ChemSpider	4940183 Y
UNII	141A6AMN38 Y
KEGG	D07698 Y
ChEBI	CHEBI:3697 Y
ChEMBL	CHEMBL766 Y
Chemical data
Formula	C16H26N2O5S
Mol. mass	358.454 g/mol
SMILES	eMolecules & PubChem
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 Y Key:DHSUYTOATWAVLW-WFVMDLQDSA-N Y
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Cilastatin is a chemical compound which inhibits the human enzyme dehydropeptidase.^[1]

Dehydropeptidase is found in the kidney and is responsible for degrading the antibiotic imipenem. Cilastatin is therefore combined intravenously with imipenem in order to protect it from dehydropeptidase and prolong its antibacterial effect. However, cilastatin itself does not have antibiotic activity.

Another carbapenem, meropenem is resistant to dehydropeptidase; therefore, it can be given without cilastatin.

References

1. ^ 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. PMC 162797. PMID 7492120. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=162797. 

See also

• Imipenem/cilastatin