cilastatin   Click here for help

GtoPdb Ligand ID: 5166

Synonyms: MK 0791 | MK-791 | MK791 | Primaxin®
Approved drug
cilastatin is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Cilastatin (sodium) is an adjunct to treatment with the antibiotic imipenem (PubChem CID 104838). Functions as a dipeptidase inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 155.02
Molecular weight 358.16
XLogP -0.52
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)C(CSCCCCC=C(C(=O)O)NC(=O)C1CC1(C)C)N
Isomeric 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
InChI Key DHSUYTOATWAVLW-WFVMDLQDSA-N
References
1. Graham DW, Ashton WT, Barash L, Brown JE, Brown RD, Canning LF, Chen A, Springer JP, Rogers EF. (1987)
Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids.
J. Med. Chem., 30 (6): 1074-90. [PMID:3495664]
2. Keynan S, Hooper NM, Felici A, Amicosante G, Turner AJ. (1995)
The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA.
Antimicrob. Agents Chemother., 39 (7): 1629-31. [PMID:7492120]