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Cilastatin

CAT: 0127-OR1027746-01Size: 100 mgDry Ice: NoHazardous: No
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CAS Number
82009-34-5
Synonyms
(Z) -7-[ (2R) -2-amino-2-carboxyethyl]sulfanyl-2-[[ (1S) -2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
Purity
98%
Smiles
CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C

Chemical Information

Cilastatin

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 xenobiotic, a protease inhibitor, an EC 3.4.13.19 (membrane dipeptidase) inhibitor and an environmental contaminant. It is an organic sulfide, a carboxamide, a non-proteinogenic L-alpha-amino acid and a L-cysteine derivative. It is a conjugate acid of a cilastatin(1-).

CAS Number82009-34-5
PubChem CID6435415
IUPAC Name(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
Molecular FormulaC16H26N2O5S
Molecular Weight358.5
XLogP-1
Topological Polar Surface Area155
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Heavy Atom Count24
Formal Charge0
Complexity519
SMILES
CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C
InChI
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
InChIKey
DHSUYTOATWAVLW-WFVMDLQDSA-N
Chemical Structure
2D Structure
2D structure of Cilastatin
CAS: 82009-34-5
CID: 6435415
Formula: C16H26N2O5S
MW: 358.5
Interactive 3D Structure
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Computed Properties
PropertyValue
Molecular Weight358.5
XLogP3-1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Exact Mass358.15624311
Monoisotopic Mass358.15624311
Topological Polar Surface Area155 Ų
Heavy Atom Count24
Formal Charge0
Complexity519
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
006831-01Cilastatin
C279-100MGCilastatin Sodium
ABDIC1010AImipenem/Cilastatin
TRC-C441130-50MGCilastatin Sulfoxide

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