Technical Data

006831
CAS Number
82009-34-5
Grade
Highly Purified
Molecular Formula
C₁₆H₂₆N₂O₅S
Molecular Weight
358.45
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
-20°C
Cilastatin
(2Z)-7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic Acid; MK-791

Prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Antibacterial adjunct.

Cilastatin is an inhibitor of dipeptidase (dehydropeptidase I), a renal dipeptidase.1 It inhibits human renal dipeptidase (Ki = 0.7uM), porcine dipeptidase (IC50 = 0.11uM), and bacterial metallo-β-lactamase CphA from A. hydrophila (IC50 = 178uM).1,2,3 Cilastatin (200ug/ml) protects primary porcine renal proximal tubular epithelial cells from nephrotoxicity and apoptosis induced by vancomycin.4 In a mouse model of systemic infection, cilastatin in combination with imipenem 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.
Synonyms
(2Z)-7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic Acid; MK-791
CAS No
82009-34-5
Molecular Formula
C₁₆H₂₆N₂O₅S
Molecular Weight
358.45
Appearance
Supplied to white to light brown solid
Purity
~98%
Solubility
DMSO, Methanol
Melting Point
143-146°C (dec)
Method for Determining Identity
Proton NMR (DMSO-d6), Spectroscopic and Mass Spectrometric Analysis
TLC Conditions
C18; Acetonitrile: Water Acetic Acid;=8:1:0.15; Visualized with UV and AMCS; Rf=0.55
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. Stable for 6 months after receipt. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards:  All products should be handled by qualified personnel only, trained in laboratory procedures.

Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.

References
1. Campbell, B.J., Forrester, L.J., Zahler, W.L., et al. Beta-lactamase activity of purified and partially characterized human renal dipeptidase J. Biol. Chem. 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. 2015, 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). 6. Finlay, K.R., et al.: Invest. Ophthalmol. Visual Sci., 24:1147 (1983) 7. Norrby, S.R., et al.: Antimicrob. Agents Chemother., 23:300 (1983) 8. Washburn, D.E., et al.: J. Antimicrob. Chemother., 12:39 (1983)
USBio References
No references available
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