(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid

• ChemBase ID: 1374
• Molecular Formular: C16H26N2O5S
• Molecular Mass: 358.45304
• Monoisotopic Mass: 358.15624294
• SMILES: [C@H]1(C(C1)(C)C)C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O
• Canonical SMILES: OC(=O)[C@H](CSCCCC/C=C(/C(=O)O)\NC(=O)[C@H]1CC1(C)C)N
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid
• IUPAC Traditional name: cilastatina
• Synonyms: Cilastatin

Database IDs

• CAS Number: 82009-34-5
• PubChem SID: 160964834; 46505611
• PubChem CID: 6435415

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.5319705
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.295944
• LogD (pH = 7.4): -4.05599
• Log P: -1.259092
• Molar Refractivity: 92.8507 cm^3
• Polarizability: 36.12875 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.29
• LOG S: -3.55
• Solubility (Water): 1.00e-01 g/l

DETAILS

DrugBank - DB01597

• Drug Groups: approved
• Description: A renal dehydropeptidase-I and leukotriene D4 dipeptidase inhibitor. Since the antibiotic, imipenem, is hydrolyzed by dehydropeptidase-I, which resides in the brush border of the renal tubule, cilastatin is administered with imipenem to increase its effectiveness. The drug also inhibits the metabolism of leukotriene D4 to leukotriene E4. [PubChem]
• Indication: Combined intravenously with imipenem in order to protect it from dehydropeptidase and prolong its antibacterial effect.
• Pharmacology: Cilastatin is a chemical compound which inhibits the human enzyme dehydropeptidase. Dehydropeptidase is found in the kidney and is responsible for degrading the antibiotic imipenem. Cilastatin is therefore combined intravenously with imipenem in order to protect it from dehydropeptidase and prolong its antibacterial effect. However, cilastatin in and of itself does not have any antibacterial activity.
• Affected Organisms: Humans and other mammals
• References: Keynan S, Hooper NM, Felici A, Amicosante G, Turner AJ: The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA. Antimicrob Agents Chemother. 1995 Jul;39(7):1629-31. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Keynan S, Hooper NM, Felici A, Amicosante G, Turner AJ: The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA. Antimicrob Agents Chemother. 1995 Jul;39(7):1629-31. Pubmed