Cilastatin sodiumProduct ingredient for Cilastatin

Name
Cilastatin sodium
Drug Entry
Cilastatin

Cilastatin is an inhibitor of renal dehydropeptidase, an enzyme responsible for both the metabolism of thienamycin beta-lactam antibiotics as well as conversion of leukotriene D4 to leukotriene E4. Since the antibiotic, imipenem, is one such antibiotic that is hydrolyzed by dehydropeptidase, cilastatin is used in combination with imipenem to prevent its metabolism. The first combination product containing both drugs was approved by the FDA in November of 1985 under the trade name Primaxin, marketed by Merck & Co.9 A newer triple-drug product was approved in July 2019 under the trade name Recarbrio which also contains relebactam.8

Accession Number
DBSALT001295
Structure
Synonyms
Not Available
External IDs
MK-791
UNII
5428WXZ74M
CAS Number
81129-83-1
Weight
Average: 380.43
Monoisotopic: 380.13818737
Chemical Formula
C16H25N2NaO5S
InChI Key
QXPBTTUOVWMPJN-QBNHLFMHSA-M
InChI
InChI=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
IUPAC Name
sodium (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoate
SMILES
[Na+].CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C([O-])=O
ChemSpider
5293165
ChEBI
59511
ChEMBL
CHEMBL1201057
Wikipedia
Cilastatin
Predicted Properties
PropertyValueSource
Water Solubility0.112 mg/mLALOGPS
logP0.22ALOGPS
logP-1.3Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)2.53Chemaxon
pKa (Strongest Basic)9.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area132.55 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity103.69 m3·mol-1Chemaxon
Polarizability37.98 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon