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82009-34-5

82009-34-5 structural image
Product Name: Cilastatin
Formula: C16H26N2O5S
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CHEMICAL AND PHYSICAL PROPERTIES

Physical Description Solid
Melting Point 655.5
Solubility 1.00e-01 g/L

COMPUTED DESCRIPTORS

Molecular Weight 358.5 g/mol
XLogP3 -1
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 7
Rotatable Bond Count 11
Exact Mass 358.15624311 g/mol
Monoisotopic Mass 358.15624311 g/mol
Topological Polar Surface Area 155 Ų
Heavy Atom Count 24
Formal Charge 0
Complexity 519
Isotope Atom Count 0
Defined Atom Stereocenter Count 2
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 1
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

PRODUCT INTRODUCTION

description

Cilastatin is the thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid. 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 is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products. Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4. It has a role as a protease inhibitor, an EC 3.4.13.19 (membrane dipeptidase) inhibitor, a xenobiotic and an environmental contaminant. It is a non-proteinogenic L-alpha-amino acid, a L-cysteine derivative, an organic sulfide and a carboxamide. It is a conjugate acid of a cilastatin(1-).

RELATED SUPPLIERS

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