TORSEMIDE

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Search structure


Trade Names	DEMADEX TORSEMIDE
Synonyms	AC-4464 AC4464 BM-02.015 BM-02015 BM02.015 Demadex Luprac Soaanz Torasemide Torasemide anhydrous Torem 10 Torem 2.5 Torem 5 Torsemide Upcard
Status
Molecule Category	UNKNOWN
UNII	W31X2H97FB
EPA CompTox	DTXSID2023690


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

Structure


InChI Key	NGBFQHCMQULJNZ-UHFFFAOYSA-N
Smiles	Cc1cccc(Nc2ccncc2S(=O)(=O)NC(=O)NC(C)C)c1
InChI	InChI=1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H20N4O3S
Molecular Weight	348.43
AlogP	2.53
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	5.0
Polar Surface Area	100.19
Molecular species	ACID
Aromatic Rings	2.0
Heavy Atoms	24.0

Bioactivity

Mechanism of Action	Action	Reference
Sodium-(potassium)-chloride cotransporter 2 inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	-	-	-	14
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	73

Assay Description	Organism	Bioactivity	Reference
Inhibition of beta-lactamase at 100 uM	None	5.0 %
Inhibition of chymotrypsin at 250 uM	unidentified	5.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM	None	14.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	73.9 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	73.29 %
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	4.19 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	6.8 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	8.97 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	3.65 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	11.62 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	2.49 %
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	0.39 %
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	0.63 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.987 %
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	0.0 %		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	0.0 %

Cross References

Resources	Reference
ChEBI	9637
ChEMBL	CHEMBL1148
DrugBank	DB00214
DrugCentral	2708
FDA SRS	W31X2H97FB
Human Metabolome Database	HMDB0014359
Guide to Pharmacology	7312
PharmGKB	PA451733
PubChem	41781
SureChEMBL	SCHEMBL41184
ZINC	ZINC000000005823

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).