An internal standard for the quantification of cilastatin
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Unlabeled Version(s)
23511Cilastatin
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Cilastatin-15N-d3

Item No. 29098

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(Z)-7-((2-(amino-15N)-2-carboxyethyl-1,1,2-d3)thio)-2-((S)-2,2-dimethylcyclopropane-1-carboxamido)hept-2-enoic acid
CAS Number
2738376-83-3
Molecular Formula
C16H23D3N[15N]O5S
Formula Weight
362.5
Purity
≥99% deuterated forms(d1-d3); ≤1% d0
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: SolubleWater: Soluble
SMILES
OC(C([15NH2])([2H])C([2H])([2H])SCCCC/C=C(C(O)=O)\NC([C@@H]1C(C)(C)C1)=O)=O
InChi Code
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/i9D2,11D,17+1
InChi Key
DHSUYTOATWAVLW-MAVRWZHLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

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    Product Description

    Cilastatin-15N-d3 is intended for use as an internal standard for the quantification of cilastatin (Item No. 23511) by GC- or LC-MS. Cilastatin is an inhibitor of dipeptidase (dehydropeptidase I), a renal dipeptidase.1 It inhibits human renal dipeptidase (Ki = 0.7 μM), porcine dipeptidase (IC50 = 0.11 μM), and bacterial metallo-β-lactamase CphA from A. hydrophila (IC50 = 178 μM).1,2,3 Cilastatin (200 μg/ml) protects primary porcine renal proximal tubular epithelial cells from nephrotoxicity and apoptosis induced by vancomycin (Item No. 15327).4 In a mouse model of systemic infection, cilastatin in combination with imipenem (Item No. 16039) protects mice from S. aureus, E. coli, and P. aeruginosa infection.5 Cilastatin was designed to inhibit renal metabolism of imipenem and prolong its half-life.2 Formulations containing cilastatin in combination with imipenem have been used to treat susceptible bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Campbell, B.J., Forrester, L.J., Zahler, W.L., et al. Beta-lactamase activity of purified and partially characterized human renal dipeptidase. The Journal of Biological Chemisty 259(23), 14586-14590 (1984).

    2. Kahan, F.M., Kropp, H., Sundelof, J.G., et al. Thienamycin: Development of imipenen-cilastatin. J. Antimicrob. Chemother. 12(Suppl. D), 1-35 (1983).

    3. Keynan, S., Hooper, N.M., Felici, A., et al. The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-β-lactamase enzyme CphA. Antimicrob. Agents Chemother. 39(7), 1629-1631 (1995).

    4. Humanes, B., Jado, J.C., Camaño, S., et al. Protective effects of cilastatin against vancomycin-induced nephrotoxicity. Biomed Res. Int. 704382 (2015).

    5. Petersen, P.J., Jacobus, N.V., Weiss, W.J., et al. In vitro and in vivo activities of LJC10,627, a new carbapenem with stability to dehydropeptidase I. Antimicrob. Agents Chemother. 35(1), 203-207 (1991).