TRICHLORMETHIAZIDE

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Search structure


Trade Names	METAHYDRIN NAQUA TRICHLOREX TRICHLORMAS TRICHLORMETHIAZIDE
Synonyms	Metahydrin NSC-61560 Naqua Trichlorex Trichlormas Trichlormethiazide Trichloromethiazide
Status
Molecule Category	Free-form
ATC	C03AA06
UNII	Q58C92TUN0
EPA CompTox	DTXSID7023699


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

Structure


InChI Key	LMJSLTNSBFUCMU-UHFFFAOYSA-N
Smiles	NS(=O)(=O)c1cc2c(cc1Cl)NC(C(Cl)Cl)NS2(=O)=O
InChI	InChI=1S/C8H8Cl3N3O4S2/c9-3-1-4-6(2-5(3)19(12,15)16)20(17,18)14-8(13-4)7(10)11/h1-2,7-8,13-14H,(H2,12,15,16)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C8H8Cl3N3O4S2
Molecular Weight	380.66
AlogP	0.82
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	2.0
Polar Surface Area	118.36
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	20.0

Pharmacology

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

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Lyase	-	-	-	134	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	82

Assay Description	Organism	Bioactivity	Reference
Inhibition of human recombinant full length CA1 by stopped-flow CO2 hydration method	Homo sapiens	345.0 nM
Inhibition of human recombinant full length CA2 by stopped-flow CO2 hydration method	Homo sapiens	91.0 nM
Inhibition of human recombinant full length CA4 by stopped-flow CO2 hydration method	Homo sapiens	449.0 nM
Inhibition of human recombinant full length CA5A by stopped-flow CO2 hydration method	Homo sapiens	763.0 nM
Inhibition of human recombinant full length CA5B by stopped-flow CO2 hydration method	Homo sapiens	134.0 nM
Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration method	Homo sapiens	7.9 nM
Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydration method	Homo sapiens	87.0 nM
Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydration method	Homo sapiens	312.0 nM
Inhibition of mouse recombinant full length CA13 by stopped-flow CO2 hydration method	Mus musculus	645.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	81.82 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	86.79 %
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	-24.21 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	17.2 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	15.18 %
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	0.21 %		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	-0.06 %		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	0.21 %		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	-0.06 %

Related Entries

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Cross References

Resources	Reference
ChEBI	9683
ChEMBL	CHEMBL1054
DrugBank	DB01021
DrugCentral	2733
FDA SRS	Q58C92TUN0
Human Metabolome Database	HMDB0015156
Guide to Pharmacology	7314
KEGG	C07767
PDB	TRU
PharmGKB	PA164752426
PubChem	5560
SureChEMBL	SCHEMBL25492
ZINC	ZINC00897236

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).