CICLOPIROX

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Search structure


Trade Names	CICLOPIROX LOPROX PENLAC
Synonyms	Ciclopirox Cyclopirox HOE 296B HOE-296B Loprox Penlac
Status
Molecule Category	UNKNOWN
ATC	D01AE14 G01AX12
UNII	19W019ZDRJ
EPA CompTox	DTXSID9048564


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

Structure


InChI Key	SCKYRAXSEDYPSA-UHFFFAOYSA-N
Smiles	Cc1cc(C2CCCCC2)n(O)c(=O)c1
InChI	InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C12H17NO2
Molecular Weight	207.27
AlogP	2.44
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	1.0
Polar Surface Area	42.23
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	15.0

Bioactivity

Mechanism of Action	Action	Reference
Aluminium chelating agent	CHELATING AGENT	PubMed PubMed Wikipedia

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	5000	-	-	0
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters	-	-	-	-	52

Assay Description	Organism	Bioactivity	Reference
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay	Homo sapiens	52.0 %
Inhibition of IDO1 (unknown origin) at highest soluble concentration using L-tryptophan substrate incubated for 60 mins by HPLC	Homo sapiens	0.0 %
Inhibition of H2O2-induced mitochondrial metabolic dysfunction in Sprague-Dawley rat primary astrocytes by resazurin-dye based presto blue assay	Rattus norvegicus	330.0 nM
Cytoprotective activity in Sprague-Dawley rat primary astrocytes assessed as inhibition of H2O2-induced cell death by LDH release assay	Rattus norvegicus	249.9 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	13.38 %
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	0.1 %		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	0.1 %

Cross References

Resources	Reference
ChEBI	453011
ChEMBL	CHEMBL1413
DrugBank	DB01188
DrugCentral	636
FDA SRS	19W019ZDRJ
Human Metabolome Database	HMDB0015319
KEGG	D03488
PDB	B4O
PharmGKB	PA164747060
PubChem	2749
SureChEMBL	SCHEMBL34424
ZINC	ZINC000000001145

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).