Chemistry:Cilastatin

Short description: Chemical compound

Cilastatin

Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a686013
Routes of administration	IV
ATC code	J01DH51 (WHO) (combination with imipenem)
Identifiers
IUPAC name (Z)-7-[(2R)-2-Amino-3-hydroxy-3-oxopropyl]sulfanyl-2-{[(1S)-2,2-dimethylcyclopropanecarbonyl]amino}hept-2-enoic acid
CAS Number	82009-34-5 Y
PubChem CID	5280454
IUPHAR/BPS	5166
DrugBank	DB01597 Y
ChemSpider	4940183 Y
UNII	141A6AMN38
KEGG	D07698 Y
ChEBI	CHEBI:3697 Y
ChEMBL	ChEMBL766 Y
Chemical and physical data
Formula	C16H26N2O5S
Molar mass	358.45 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N\C(=C/CCCCSC[C@@H](C(=O)O)N)C(=O)O)[C@H]1CC1(C)C
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 inhibits the human enzyme dehydropeptidase.

Uses

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 degradation, prolonging its antibacterial effect.

Imipenem alone is an effective antibiotic and can be given without cilastatin. Cilastatin itself does not have antibiotic activity, although it has been proved to be active against a zinc-dependent beta-lactamase that usually confers antibiotic resistance to certain bacteria, more precisely, the carbapenem family of antibiotics. This property is due to the physicochemical similarities between membrane dipeptidase (MDP), the compound it is usually set to target, and the bacterial metallo-beta-lactamase carried by the CphA gene. 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.