Cilastatin sodium (CHEM019351)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:02:35 UTC
Update Date2016-11-09 01:15:58 UTC
Accession NumberCHEM019351
Identification
Common NameCilastatin sodium
ClassSmall Molecule
DescriptionThe 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 administered with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to microbiologically inactive and potentially nephrotoxic products.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-(S)-6-Carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine monosodium saltChEBI
Sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoateChEBI
Sodium (Z)-7-(((R)-2-amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoateChEBI
CSKegg
Sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acidGenerator
Sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulphanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoateGenerator
Sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulphanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acidGenerator
Sodium (Z)-7-(((R)-2-amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acidGenerator
Sodium;(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acidGenerator
Sodium;(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulphanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoateGenerator
Sodium;(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulphanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acidGenerator
CilastatinMeSH
Cilastatin monosodium saltMeSH
Cilastatin sodiumMeSH
Monosodium salt, cilastatinMeSH
Salt, cilastatin monosodiumMeSH
Sodium, cilastatinMeSH
Chemical FormulaC16H25N2NaO5S
Average Molecular Mass380.430 g/mol
Monoisotopic Mass380.138 g/mol
CAS Registry Number81129-83-1
IUPAC Namesodium (1S)-N-[(1Z)-6-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-1-carboxyhex-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboximidate
Traditional Namesodium (1S)-N-[(1Z)-6-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-1-carboxyhex-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboximidate
SMILES[Na+].[H]\C(CCCCSC[C@]([H])(N)C(O)=O)=C(\N=C([O-])[C@@]1([H])CC1(C)C)C(O)=O
InChI IdentifierInChI=1S/C16H26N2O5S.Na/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);/q;+1/p-1/b12-6-;/t10-,11+;/m1./s1
InChI KeyQXPBTTUOVWMPJN-QBNHLFMHSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-phenylthioureas. These are thiourea derivatives where one nitrogen atom of the urea group is linked to a phenyl group and the other is acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassN-phenylthioureas
Direct ParentN-acyl-phenylthioureas
Alternative Parents
Substituents
  • N-acyl-phenylthiourea
  • Acetanilide
  • Benzoic acid or derivatives
  • Phenylpropane
  • Anilide
  • N-acetylarylamine
  • Benzoyl
  • N-arylamide
  • Acetamide
  • Thiourea
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.091 g/LALOGPS
logP-0.26ALOGPS
logP-0.46ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.04 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity103.92 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0129000000-8e2a131a05701f149adaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w0-5569000000-dcbd8fd409fb00e78fceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-9410000000-d75e1ca7e2c3f3961156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p5-4139000000-0dbf20c2d5fb3649c752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9761000000-bb2d7e9cbf3d785ba173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9010000000-675b22958534e8ddac2dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCilastatin
Chemspider IDNot Available
ChEBI ID59511
PubChem Compound ID6917946
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available