METOLAZONE

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Search structure


Trade Names	DIULO METOLAZONE MYKROX ZAROXOLYN
Synonyms	Diulo Metazoline Metenix Metolazone Metozalone Mykrox NSC-759581 Normelan Oldren SR 720-22 SR-720-22 Xuret Zaroxolyn
Status
Molecule Category	UNKNOWN
ATC	C03BA08
UNII	TZ7V40X7VX
EPA CompTox	DTXSID6045167


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

Structure


InChI Key	AQCHWTWZEMGIFD-UHFFFAOYSA-N
Smiles	Cc1ccccc1N1C(=O)c2cc(S(N)(=O)=O)c(Cl)cc2NC1C
InChI	InChI=1S/C16H16ClN3O3S/c1-9-5-3-4-6-14(9)20-10(2)19-13-8-12(17)15(24(18,22)23)7-11(13)16(20)21/h3-8,10,19H,1-2H3,(H2,18,22,23)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H16ClN3O3S
Molecular Weight	365.84
AlogP	2.71
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	2.0
Polar Surface Area	92.5
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	24.0

Bioactivity

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

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Lyase	-	-	-	2	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	62

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	62.42 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	66.79 %
Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins by stopped flow CO2 hydration assay	Homo sapiens	2.1 nM
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	-2.19 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.514 %
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	-0.05 %		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	-0.05 %

Related Entries

Cross References

Resources	Reference
ChEBI	64354
ChEMBL	CHEMBL878
DrugBank	DB00524
DrugCentral	1783
FDA SRS	TZ7V40X7VX
Human Metabolome Database	HMDB0014665
Guide to Pharmacology	4838
KEGG	D00431
PharmGKB	PA164781022
PubChem	4170
SureChEMBL	SCHEMBL40558
ZINC	ZINC00896755

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).