FEXINIDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H13N3O3S
Molecular Weight	279.315
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1

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

Molecular Formula	C12H13N3O3S
Molecular Weight	279.315
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25039421 | https://www.ncbi.nlm.nih.gov/pubmed/20439607 | https://www.ncbi.nlm.nih.gov/pubmed/24841257

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial DNA synthesis 1 Target ID: bacterial DNA synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439607	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
African trypanosomiasis 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25039421	Curative	Phase III 656	Unknown Approved Use Unknown
visceral leishmaniasis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22301556	Curative	Phase II 1132	Unknown Approved Use Unknown
Chagas disease 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24841257	Curative	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The activity of fexinidazole (HOE 239) against experimental infections with Trypanosoma cruzi, trichomonads and Entamoeba histolytica.	1983 Feb	6411009
Fexinidazole--a new oral nitroimidazole drug candidate entering clinical development for the treatment of sleeping sickness.	2010 Dec 21	21200426
The anti-trypanosome drug fexinidazole shows potential for treating visceral leishmaniasis.	2012 Feb 1	22301556
The anti-tubercular drug delamanid as a potential oral treatment for visceral leishmaniasis.	2016 May 24	27215734

Patents

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:20:50 GMT 2023` Edited by `admin` on `Fri Dec 15 17:20:50 GMT 2023`
Record UNII	306ERL82IR
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FEXINIDAZOLE

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 [USAN]

Common Name

English

FEXINIDAZOLE [ORANGE BOOK]

Common Name

English

Fexinidazole [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277