CYCLOTHIAZIDE

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Search structure


Trade Names	ANHYDRON FLUIDIL
Synonyms	35483 Anhydron Cyclothiazide Fluidil NSC-758431
Status
Molecule Category	UNKNOWN
ATC	C03AA09
UNII	P71U09G5BW
EPA CompTox	DTXSID3022871


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

Structure


InChI Key	BOCUKUHCLICSIY-UHFFFAOYSA-N
Smiles	NS(=O)(=O)c1cc2c(cc1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O
InChI	InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C14H16ClN3O4S2
Molecular Weight	389.89
AlogP	1.23
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	24.0

Bioactivity

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

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Ligand-gated ion channel Ionotropic glutamate receptor AMPA receptor	1000-19800	6100	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antiallodynic activity in Sprague-Dawley rat model of spared nerve injury-induced allodynia assessed as inhibition of electrically evoked inhibitory post-synaptic current amplitude in spinal cord by electrophysiology method	Rattus norvegicus	37.9 %
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	-32.15 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	13.39 %
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	0.04 %		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	0.04 %

Related Entries

Cross References

Resources	Reference
ChEBI	31448
ChEMBL	CHEMBL61593
DrugBank	DB00606
DrugCentral	761
FDA SRS	P71U09G5BW
Human Metabolome Database	HMDB0014744
Guide to Pharmacology	4167
KEGG	C12685
PharmGKB	PA449168
PubChem	2910
SureChEMBL	SCHEMBL121096

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).