| Identification | More | [Name]
Cilastatin sodium | [CAS]
81129-83-1 | [Synonyms]
2-heptenoicacid,7-((2-amino-2-carboxyethyl)thio)-2-(((2,2-dimethylcyclopropyl
l642957
monosodiumsalt,(r-(r*,s*(z)))-)carbonyl)amino)
sodium hydrogen [R-[R*,S*-(Z)]]-7-[(2-amino-2-carboxylatoethyl)thio]-2-[[(2,2-dimethylcyclopropyl)carbonyl]amino]hept-2-enoate
Cilastatine
Cilastatin sodium
Sodium 7-(2-amino-2-carboxy-ethyl)sulfanyl-2-(2,2-dimethylcyclopropyl)carbonylamino-hept-2-enoate
Sodium hydrogen 7-[(2-amino-2-carboxylatoethyl)thio]-2-[[(2,2-dimethylcyclopropyl)carbonyl]amino]hept-2-enoate
Sodium Cilastatin
[R-[R*,S*-(Z)]]-7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)carbonyl]amino]-2-heptenoic acid monosodium salt
(Z)-7-[(R)-2-Amino-2-carboxyethylthio]-2-[(S)-2,2-dimethylcyclopropylcarbonylamino]-2-heptenoic acid 1-sodium salt | [EINECS(EC#)]
279-694-4 | [Molecular Formula]
C16H24N2Na2O5S | [MDL Number]
MFCD01723687 | [Molecular Weight]
402.42 | [MOL File]
81129-83-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White or light yellow amorphous, hygroscopic powder. | [Melting point ]
>160°C (dec.) | [Fp ]
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 ]
neat | [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) |
| Hazard Information | Back Directory | [Description]
Cilastatin Na (81129-83-1) is a dehydropeptidase-1 inhibitor. Inhibits the proteolytic conversion of leukotriene D4?to 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.2?Cilastatin 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]
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) White?et al.?(1999),?A continuous fluorometric assay for Leukotriene D4 hydrolase; Anal. Biochem.,?268?245
2) Graham?et al.?(1987),?Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-acylamino-3-substituted propenoic acids; J. Med. Chem.,?30?1074
3) Keynan?et al. (1995),?The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA; Antimicreob. Agents Chemother.,?39?1629
4) Park?et al.?(2016),?Dehydropeptidase 1 promotes metastasis through regulation of E-cadherin expression in colon cancer; Oncotarget,?7?9501 |
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