FEXINIDAZOLE

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Search structure


Synonyms	Fexinidazole HOE 239 HOE-239
Status
Molecule Category	UNKNOWN
ATC	P01CA03
UNII	306ERL82IR
EPA CompTox	DTXSID00208448


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

Structure


InChI Key	MIWWSGDADVMLTG-UHFFFAOYSA-N
Smiles	CSc1ccc(OCc2ncc([N+](=O)[O-])n2C)cc1
InChI	InChI=1S/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C12H13N3O3S
Molecular Weight	279.32
AlogP	2.63
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	5.0
Polar Surface Area	70.19
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	19.0

Bioactivity

Mechanism of Action	Action	Reference
Cytotoxic	None	PubMed PubMed PubMed

Assay Description	Organism	Bioactivity	Reference
Antimicrobial activity against Trypanosoma brucei rhodesiense after 48 hrs by proliferation assay	Trypanosoma brucei rhodesiense	700.0 nM
Cytotoxicity against in rat L6 cells assessed as reduction in cell viability after 70 hrs by alamar blue assay	Rattus norvegicus	90.0 ug.mL-1
Antileishmanial activity against Leishmania donovani LV9 amastigotes infected in BALB/c mouse assessed as reduction in parasite burden at 200 mg/kg, po administered qd for 5 days	Leishmania donovani	98.0 %
Antitrypanosomal activity against trypomastigote stage of Trypanosoma brucei brucei AnTat 1.9 assessed as decrease in parasite viability after 69 hrs by Alamar Blue assay	Trypanosoma brucei brucei	400.0 nM
Antitrypanosomal activity against trypomastigote stage of Trypanosoma brucei brucei AnTat 1.9 assessed as decrease in parasite viability after 69 hrs by Alamar blue assay	Trypanosoma brucei brucei	600.0 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	19.95 %
Antitrypanosomal activity against Trypanosoma brucei brucei AnTat 1.9 trypomastigotes assessed as reduction in parasite viability incubated for 69 hrs by Alamar Blue dye based assay	Trypanosoma brucei brucei	400.0 nM
Antitrypanosomal activity against trypomastigote stage of Trypanosoma brucei brucei AnTat 1.9 assessed as decrease in parasite viability after 69 hrs by Alamar Blue assay	Trypanosoma brucei brucei	600.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.15 %
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 %
Antileishmanial activity against Trypanosoma brucei brucei AnTat 1.9 measured after 74 hrs by Alamar blue assay	Trypanosoma brucei brucei	600.0 nM
Antitrypanosomal activity against bloodstream form Trypanosoma brucei brucei AnTat 1.9 trypomastigotes assessed as reduction in parasite viability incubated for 69 hrs by Alamar Blue dye based assay	Trypanosoma brucei brucei	600.0 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL1631694
DrugBank	DB12265
FDA SRS	306ERL82IR
PubChem	68792
SureChEMBL	SCHEMBL1163575
ZINC	ZINC000000001448

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).