TIOCONAZOLE

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Search structure


Trade Names	TIOCONAZOLE TZ-3 VAGISTAT-1
Synonyms	NSC-759169 Tioconazole Trosyl Tz-3 UK-20,349 UK-20349 Vagistat Vagistat-1
Status
Molecule Category	UNKNOWN
ATC	D01AC07 G01AF08
UNII	S57Y5X1117
EPA CompTox	DTXSID3046619


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

Structure


InChI Key	QXHHHPZILQDDPS-UHFFFAOYSA-N
Smiles	Clc1ccc(C(Cn2ccnc2)OCc2ccsc2Cl)c(Cl)c1
InChI	InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H13Cl3N2OS
Molecular Weight	387.72
AlogP	5.86
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	6.0
Polar Surface Area	27.05
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Cytochrome P450 51 inhibitor	INHIBITOR	PubMed PubMed PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 17 Cytochrome P450 family 17A Cytochrome P450 17A1	-	-	-	505	-
Enzyme Oxidoreductase	-	-	-	-	0

Assay Description	Organism	Bioactivity	Reference
In vitro inhibition of human Cytochrome P450 17A1 activity	Homo sapiens	505.0 nM
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control	Mus musculus	55.0 %
Inhibition of IDO1 (unknown origin) at highest soluble concentration using L-tryptophan substrate incubated for 60 mins by HPLC	Homo sapiens	0.0 %
DNDI: Chagas in Vitro, 96 hour	Trypanosoma cruzi	64.0 nM
DNDI: HAT in Vitro, 72 hour	Trypanosoma brucei rhodesiense	530.0 nM
DNDI: Malaria in Vitro, 72 hour	Plasmodium falciparum	630.0 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	50.58 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.542 %
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	0.02 %		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	0.02 %

Related Entries

Cross References

Resources	Reference
ChEBI	77898
ChEMBL	CHEMBL1200438
DrugBank	DB01007
DrugCentral	2675
FDA SRS	S57Y5X1117
Human Metabolome Database	HMDB0015142
KEGG	C08082
PharmGKB	PA164746156
PubChem	5482
SureChEMBL	SCHEMBL41354
ZINC	ZINC00897385

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).