cilastatin   

GtoPdb Ligand ID: 5166

Synonyms: MK 0791 | MK-791 | MK791 | Primaxin®
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.
2D Structure
Click here for structure editor
Physico-chemical Properties
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1985))
IUPAC Name
(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid
International Nonproprietary Names
INN number INN
5457 cilastatin
Synonyms
MK 0791 | MK-791 | MK791 | Primaxin®
Database Links
Specialist databases
AntibioticDB 1012, 65
Other databases
CAS Registry No. 82009-34-5
ChEBI CHEBI:3697
ChEMBL Ligand CHEMBL766
DrugBank Ligand DB01597
DrugCentral Ligand 640
GtoPdb PubChem SID 178101856
PubChem CID 6435415
Search Google for chemical match using the InChIKey DHSUYTOATWAVLW-WFVMDLQDSA-N
Search Google for chemicals with the same backbone DHSUYTOATWAVLW
Search PubMed clinical trials cilastatin
Search PubMed titles cilastatin
Search PubMed titles/abstracts cilastatin
Search UniChem for chemical match using the InChIKey DHSUYTOATWAVLW-WFVMDLQDSA-N
Search UniChem for chemicals with the same backbone DHSUYTOATWAVLW
Wikipedia Cilastatin