BUMETANIDE

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Search structure


Trade Names	BUMETANIDE BUMEX
Synonyms	Betinex Bumetanide Bumex Burinex Lixil RO 10-6338 RO-10-6338 RO-106338 S-95008. S95008.
Status
Molecule Category	UNKNOWN
ATC	C03CA02
UNII	0Y2S3XUQ5H
EPA CompTox	DTXSID5022699


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

Structure


InChI Key	MAEIEVLCKWDQJH-UHFFFAOYSA-N
Smiles	CCCCNc1cc(C(=O)O)cc(S(N)(=O)=O)c1Oc1ccccc1
InChI	InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C17H20N2O5S
Molecular Weight	364.42
AlogP	3.04
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	8.0
Polar Surface Area	118.72
Molecular species	ACID
Aromatic Rings	2.0
Heavy Atoms	25.0

Bioactivity

Mechanism of Action	Action	Reference
Sodium-(potassium)-chloride cotransporter 2 inhibitor	INHIBITOR	DOI Wikipedia Wikipedia FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	72

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	71.95 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	83.27 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	10.97 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	5.78 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	11.75 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	10.04 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	31.98 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	3.22 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	1.0 %
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	87.45 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	30.63 %
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	-0.3 %		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	-0.3 %
Inhibition of NKCC1 (unknown origin) transfected in HEK293 cells expressing mbYFPQS plasmid assessed as reduction in Cl- influx at 10 uM incubated for 30 mins by fluorescence multiplate reader analysis relative to control	Homo sapiens	58.8 %
Inhibition of NKCC1 (unknown origin) transfected in HEK293 cells expressing mbYFPQS plasmid assessed as reduction in Cl- influx at 100 uM incubated for 30 mins by fluorescence multiplate reader analysis relative to control	Homo sapiens	71.7 %
Inhibition of NKCC1 in mouse primary hippocampal neurons assessed as reduction of Ca2+ uptake at 10 uM incubated for 15 mins by Fluo-4AM dye based fluorescence analysis relative to control	Mus musculus	51.9 %
Inhibition of NKCC1 in mouse primary hippocampal neurons assessed as reduction of Ca2+ uptake at 100 uM incubated for 15 mins by Fluo-4AM dye based fluorescence analysis relative to control	Mus musculus	54.7 %

Related Entries

Cross References

Resources	Reference
ChEBI	3213
ChEMBL	CHEMBL1072
DrugBank	DB00887
DrugCentral	427
FDA SRS	0Y2S3XUQ5H
Human Metabolome Database	HMDB0015024
Guide to Pharmacology	4837
KEGG	D00247
PharmGKB	PA448682
PubChem	2471
SureChEMBL	SCHEMBL27525
ZINC	ZINC000003813061

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).