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Cilastatin sodium

Product NameCilastatin sodium
CAS81129-83-1
MFC16H25N2O5S.Na
MW380.44
EINECS279-694-4
MOL File81129-83-1.mol

Chemical Properties

Melting point	>160°C (dec.)
Flash point	87℃
storage temp.	2-8°C
solubility	Very soluble in water and in methanol, slightly soluble in anhydrous ethanol, very slightly soluble in dimethyl sulfoxide, practically insoluble in acetone and in methylene chloride.
form	Solid
pka	pKa1 2.0; pKa2 4.4; pKa3 9.2(at 25℃)
color	White
biological source	synthetic (organic)
Water Solubility	water: 10mg/mL, clear, colorless to faintly yellow
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey	QXPBTTUOVWMPJN-LZTDVXLXNA-M
SMILES	[C@H]1(C(=O)N/C(=C\CCCCSC[C@H](N)C(O)=O)/C(=O)[O-])CC1(C)C.[Na+] \|&1:0,12,r\|
CAS DataBase Reference	81129-83-1(CAS DataBase Reference)

Safety Information

WGK Germany	WGK 3
RTECS	MJ9650200
HS Code	2941.90.1050
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Cilastatin Na (81129-83-1) is a dehydropeptidase-1 inhibitor. Inhibits the proteolytic conversion of leukotriene D4to E4.1 Inhibits the mammalian β-lactamase renal dipeptidase (dehydropeptidase-1, DPEP1) and thus is used as an antibacterial adjunct to extend the half-life of β-lactam antibiotics.2Cilastatin also inhibits bacterial metallo-β-lactamase and thereby may block resistance to the carbapenem family of antibiotics in certain bacteria.3 Suppresses invasion and metastasis of DPEP1-expressing tumor cells.4

Chemical Properties

White or light yellow amorphous, hygroscopic powder.

Uses

Cilastatin sodium is a dipeptidase inhibitor with nephroprotective effects.

Uses

Enzyme inhibitor.

Definition

ChEBI: The monosodium salt of cilastatin. 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 sodium is therefore administ red with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to microbiologically inactive and potentially nephrotoxic products.

General Description

Cilastatin sodium salt is off-white to yellowish-white, hygroscopic, amorphous compound. It is derivatized from heptenoic acid. Its molecular mass is 380.43 g.

Biological Activity

Dipeptidase inhibitor (LTDase, leukotriene D4 hydrolase, dehydropeptidase I) that displays a K i value of 0.11 μ M. Inhibits metabolism of LTD 4 to LTE 4 and the hydrolysis of β -lactam antibiotics. Nephroprotective; reduces toxic accumulation of cyclosporin A in kidney proximal tubule epithelial cells.

Biochem/physiol Actions

Inhibitor of the renal enzyme dehydropeptidase I and some bacterial zinc-containing β-lactamases. By these action, cilastatin suppresses both host and target metabolism of the broad-spectrum antibiotic imipenem, improving its efficacy.

References

[1] A continuous fluorometric assay for Leukotriene D4 hydrolase
[2] DONALD W. GRAHAM. Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids[J]. Journal of Medicinal Chemistry, 1987, 30 6: 1074-1090. DOI:10.1021/jm00389a018
[3] S KEYNAN. The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA.[J]. Antimicrobial Agents and Chemotherapy, 1995, 39 7: 1629-1631. DOI:10.1128/aac.39.7.1629
[4] S. PARK. Dehydropeptidase 1 promotes metastasis through regulation of E-cadherin expression in colon cancer[J]. Oncotarget, 2016, 7 1: 9501-9512. DOI:10.18632/oncotarget.7033

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