CILASTATIN

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Search structure


Synonyms	Cilastatin Primaxin
Status
Molecule Category	UNKNOWN
UNII	141A6AMN38
EPA CompTox	DTXSID8048238


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	DHSUYTOATWAVLW-WFVMDLQDSA-N
Smiles	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H26N2O5S
Molecular Weight	358.46
AlogP	1.43
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	11.0
Polar Surface Area	129.72
Molecular species	ZWITTERION
Aromatic Rings	0.0
Heavy Atoms	24.0

Bioactivity

Mechanism of Action	Action	Reference
Renal dipeptidase inhibitor	INHIBITOR	PubMed PubMed PubMed Wikipedia

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Metallo protease Metallo protease MJ clan Metallo protease M19 family	-	-	-	110-210	-

Assay Description	Organism	Bioactivity	Reference
Inhibitory activity against beta-lactamase renal dipeptidase	None	190.0 nM		Inhibitory activity against beta-lactamase renal dipeptidase	None	110.0 nM		Inhibitory activity against beta-lactamase renal dipeptidase	None	210.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.14 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.83 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.08 %

Cross References

Resources	Reference
ChEBI	3697
ChEMBL	CHEMBL766
DrugBank	DB01597
DrugCentral	640
FDA SRS	141A6AMN38
Human Metabolome Database	HMDB0015535
Guide to Pharmacology	5166
KEGG	C01675
PharmGKB	PA448998
PubChem	6435415
SureChEMBL	SCHEMBL37051
ZINC	ZINC000004095696

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).