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
- External Links
- ChemSpider
- 5293165
- ChEBI
- 59511
- ChEMBL
- CHEMBL1201057
- Wikipedia
- Cilastatin
- Predicted Properties
Property Value Source Water Solubility 0.112 mg/mL ALOGPS logP 0.22 ALOGPS logP -1.3 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 2.53 Chemaxon pKa (Strongest Basic) 9.14 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 132.55 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 103.69 m3·mol-1 Chemaxon Polarizability 37.98 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon