BENZTHIAZIDE

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Trade Names	AQUATAG BENZTHIAZIDE EXNA FOVANE URESE
Synonyms	Aquatag Benzothiazide Benzthiazide Exna Fovane NSC-755902 Urese
Status
Molecule Category	UNKNOWN
UNII	1TD8J48L61
EPA CompTox	DTXSID4022658


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

Structure


InChI Key	NDTSRXAMMQDVSW-UHFFFAOYSA-N
Smiles	NS(=O)(=O)c1cc2c(cc1Cl)N=C(CSCc1ccccc1)NS2(=O)=O
InChI	InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C15H14ClN3O4S3
Molecular Weight	431.95
AlogP	2.24
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	5.0
Polar Surface Area	118.69
Molecular species	ACID
Aromatic Rings	2.0
Heavy Atoms	26.0

Pharmacology

Mechanism of Action	Action	Reference
Thiazide-sensitive sodium-chloride cotransporter inhibitor	INHIBITOR	DOI

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	-	-	-	-	57
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	57430	-	-	-

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	74.12 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	56.86 %
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	6.42 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.935 %
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	0.12 %		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	0.12 %

Related Entries

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Cross References

Resources	Reference
ChEBI	3047
ChEMBL	CHEMBL1201039
DrugBank	DB00562
DrugCentral	332
FDA SRS	1TD8J48L61
Human Metabolome Database	HMDB0014702
Guide to Pharmacology	7125
KEGG	C07759
PharmGKB	PA164776841
PubChem	2343
SureChEMBL	SCHEMBL26257
ZINC	ZINC000003871698

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).