U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H13N3O3S
Molecular Weight 279.3165
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FEXINIDAZOLE

SMILES

Cn1c(COc2ccc(cc2)SC)ncc1N(=O)=O

InChI

InChIKey=MIWWSGDADVMLTG-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Fexinidazole is an antiparasitic drug, which is in the phase III of clinical trial for the treatment of Human African Trypanosomiasis, and in the phase II for the treatment Disease, Chagas and Visceral Leishmaniosis. However, for the Visceral Leishmaniosis, studies were terminated, due to lack of efficacy. Fexinidazole rapidly metabolized to two active metabolites, a sulfone and a sulfoxide, which prolong the pharmacological action of parent drug. These metabolites retaine trypanocidal activity but are less effective in nifurtimox-resistant lines, which can lead to the potential danger in the use of fexinidazole as a monotherapy.

CNS Activity

Curator's Comment:: Known to be CNS penetrant in mouse. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: bacterial DNA synthesis
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The activity of fexinidazole (HOE 239) against experimental infections with Trypanosoma cruzi, trichomonads and Entamoeba histolytica.
1983 Feb
Fexinidazole--a new oral nitroimidazole drug candidate entering clinical development for the treatment of sleeping sickness.
2010 Dec 21
The anti-trypanosome drug fexinidazole shows potential for treating visceral leishmaniasis.
2012 Feb 1
The anti-tubercular drug delamanid as a potential oral treatment for visceral leishmaniasis.
2016 May 24
Patents

Sample Use Guides

Fexinidazole, 600 mg tablets given by oral route, after the main daily meal (within 30 minutes from the start of the meal), at the daily dose of: 1 800 mg (3 tablets) once a day for 4 days, followed by 1 200 mg (2 tablets) once a day for 6 days. Total duration of treatment will be 10 days.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
FEXINIDAZOLE
INN  
INN   USAN  
Official Name English
1-METHYL-2-((P-(METHYLTHIO)PHENOXY)METHYL)-5-NITROIMIDAZOLE
Common Name English
FEXINIDAZOLE [INN]
Common Name English
1-METHYL-2-((4-(METHYLTHIO)PHENOXY)METHYL)-5-NITRO-1H-IMIDAZOLE
Systematic Name English
1H-IMIDAZOLE, 1-METHYL-2-((4-(METHYLTHIO)PHENOXY)METHYL)-5-NITRO-
Systematic Name English
HOE-239
Code English
FEXINIDAZOLE [WHO-DD]
Common Name English
FEXINIDAZOLE [USAN]
USAN  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
WHO-ATC P01CA03
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
FDA ORPHAN DRUG 513915
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C65680
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
PUBCHEM
68792
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
EVMPD
SUB07618MIG
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
CAS
59729-37-2
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
WIKIPEDIA
FEXINIDAZOLE
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
DRUG BANK
DB12265
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
FDA UNII
306ERL82IR
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
INN
4142
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL1631694
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
EPA CompTox
59729-37-2
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY
MESH
C038307
Created by admin on Sat Jun 26 08:11:21 UTC 2021 , Edited by admin on Sat Jun 26 08:11:21 UTC 2021
PRIMARY