SPARFLOXACIN

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Search structure


Trade Names	ZAGAM
Synonyms	AT-4140 CI-978 NSC-759641 Spara Sparfloxacin Zagam
Status
Molecule Category	UNKNOWN
ATC	J01MA09
UNII	Q90AGA787L
EPA CompTox	DTXSID9023590


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

Structure


InChI Key	DZZWHBIBMUVIIW-DTORHVGOSA-N
Smiles	C[C@@H]1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C[C@H](C)N1
InChI	InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H22F2N4O3
Molecular Weight	392.41
AlogP	2.08
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	3.0
Polar Surface Area	100.59
Molecular species	ZWITTERION
Aromatic Rings	2.0
Heavy Atoms	28.0

Bioactivity

Mechanism of Action	Action	Reference
Bacterial DNA gyrase inhibitor	INHIBITOR	FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	18000-46900	-	-	-
Ion channel Voltage-gated ion channel Voltage-gated calcium channel	-	88800	-	-	-

Assay Description	Organism	Bioactivity	Reference
Iinhibitory activity against Escherichia coli DNA gyrase	Escherichia coli	0.25 ug.mL-1
Iinhibitory activity against Staphylococcus aureus DNA gyrase	Staphylococcus aureus	14.0 ug.mL-1
Iinhibitory activity against Escherichia coli DNA topoisomerase IV	Escherichia coli	6.9 ug.mL-1
Iinhibitory activity against Staphylococcus aureus DNA topoisomerase IV	Staphylococcus aureus	14.0 ug.mL-1
Iinhibitory activity against human DNA topoisomerase II	Homo sapiens	400.0 ug.mL-1
Clonogenic cytotoxicity against Chinese hamster V-79 cells	Cricetulus griseus	370.0 ug.mL-1
Inhibition of Bacillus subtilis topoisomerase4 activity	Bacillus subtilis	0.4 ug.mL-1
Inhibition of Bacillus subtilis gyrase activity	Bacillus subtilis	0.5 ug.mL-1
Inhibition of Mycobacterium leprae recombinant DNA gyrase expressed in Escherichia coli assessed as inhibition of pBR322 DNA supercoiling	Mycobacterium leprae	5.0 ug.mL-1
Antitubercular activity against Mycobacterium tuberculosis	Mycobacterium tuberculosis	0.25 ug.mL-1
Inhibition of RNA synthesis in Mycobacterium bovis BCG assessed as inhibition of [3H]uracil incorporation by liquid scintillation counting	Mycobacterium bovis BCG	7.3 ug.mL-1
Inhibition of protein synthesis in Mycobacterium bovis BCG assessed as inhibition of [3H]leucine incorporation by liquid scintillation counting	Mycobacterium bovis BCG	11.4 ug.mL-1
Inhibition of DNA synthesis in Mycobacterium bovis BCG assessed as inhibition of [3H]adenine incorporation by liquid scintillation counting	Mycobacterium bovis BCG	16.7 ug.mL-1
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	-1.78 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-5.698 %
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	-0.14 %		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	-0.14 %

Related Entries

Cross References

Resources	Reference
ChEBI	9212
ChEMBL	CHEMBL850
DrugBank	DB01208
DrugCentral	2466
FDA SRS	Q90AGA787L
Human Metabolome Database	HMDB0015339
Guide to Pharmacology	10860
KEGG	C07662
PharmGKB	PA451472
PubChem	60464
SureChEMBL	SCHEMBL41311
ZINC	ZINC000000538362

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).