CINOXACIN

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Search structure


Trade Names	CINOBAC CINOXACIN
Synonyms	64716 Cinobac Cinoxacin NSC-304467
Status
Molecule Category	UNKNOWN
ATC	J01MB06
UNII	LMK22VUH23
EPA CompTox	DTXSID8022822


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

Structure


InChI Key	VDUWPHTZYNWKRN-UHFFFAOYSA-N
Smiles	CCn1nc(C(=O)O)c(=O)c2cc3c(cc21)OCO3
InChI	InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C12H10N2O5
Molecular Weight	262.22
AlogP	0.84
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	90.65
Molecular species	ACID
Aromatic Rings	2.0
Heavy Atoms	19.0

Bioactivity

Mechanism of Action	Action	Reference
Bacterial DNA gyrase inhibitor	INHIBITOR	FDA ISBN

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	-	-	-	3
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	102

Assay Description	Organism	Bioactivity	Reference
Inhibition of beta-lactamase at 100 uM	None	5.0 %
Inhibition of chymotrypsin at 250 uM	unidentified	5.0 %
Inhibitory concentration in supercoiling inhibition Escherichia coli DNA gyrase assay	Escherichia coli	100.0 ug.mL-1
Compound was tested for the inhibition of malate dehydrogenase (MDH) at 50 uM	None	5.0 %
Inhibition of human FAAH at 1 uM	Homo sapiens	3.36 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	112.16 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	101.46 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-8.16 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	23.26 %
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	-0.03 %		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	-0.03 %

Cross References

Resources	Reference
ChEBI	3716
ChEMBL	CHEMBL1208
DrugBank	DB00827
DrugCentral	657
FDA SRS	LMK22VUH23
Human Metabolome Database	HMDB0014965
KEGG	C08052
PharmGKB	PA449007
PubChem	2762
SureChEMBL	SCHEMBL43770
ZINC	ZINC000000032350

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).