NIFUROXAZIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H9N3O5
Molecular Weight	275.217
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C(=O)N\N=C\C2=CC=C(O2)[N+]([O-])=O

InChI

InChIKey=YCWSUKQGVSGXJO-NTUHNPAUSA-N

InChI=1S/C12H9N3O5/c16-9-3-1-8(2-4-9)12(17)14-13-7-10-5-6-11(20-10)15(18)19/h1-7,16H,(H,14,17)/b13-7+

HIDE SMILES / InChI

Molecular Formula	C12H9N3O5
Molecular Weight	275.217
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.moncoinsante.co.uk/ercefuryl-nifuroxazide-200-mg-sanofi-aventis-boite-de-12-gelules.html | https://www.ncbi.nlm.nih.gov/pubmed/18824601 | https://www.ncbi.nlm.nih.gov/pubmed/25811798 | https://www.ncbi.nlm.nih.gov/pubmed/26830149 | https://www.ncbi.nlm.nih.gov/pubmed/26154152 | https://www.ncbi.nlm.nih.gov/pubmed/28055016

Nifuroxazide is a nitrofuran antibiotic used for the treatment of acute infectious diarrhoea.Nifuroxazide is a potent inhibitor of Signal transducers and activators of transcription (STAT) signaling. It exerts antineoplastic potential both in vitro and in vivo.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Signal transducer and activator of transcription 3 10 Target ID: CHEMBL4026 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18824601	Inhibitor 8504		3.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25811798 https://www.ncbi.nlm.nih.gov/pubmed/26830149 https://www.ncbi.nlm.nih.gov/pubmed/26154152 https://www.ncbi.nlm.nih.gov/pubmed/28055016	Primary		Preclinical	Unknown Approved Use Unknown
Infectious diarrhea 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7671647 https://www.ncbi.nlm.nih.gov/pubmed/2666238 https://www.ncbi.nlm.nih.gov/pubmed/28144199	Curative		Approved 8583	ERCEFURYL Approved Use Ercéfuryl Nifuroxazide 200 mg Capsules contain a gastro-intestinal antibiotic, nifuroxazide. They can be used to treat acute, infectious diarrhoea.

Doses

Dose	Population	Adverse events
400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	Other AEs: Nausea, Vomiting... Other AEs: Nausea (30%) Vomiting (30%) Diarrhoea (20%) Abdominal cramps (20%) Rash (10%) Fever (10%) Transaminases increased (10%) Neutropenia (10%) Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/

AEs

AE	Significance	Dose	Population
Fever	10%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Neutropenia	10%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Rash	10%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Transaminases increased	10%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Abdominal cramps	20%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Diarrhoea	20%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Nausea	30%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/
Vomiting	30%	400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9365765/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	substrate 9

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP2C19 2057 CYP1A2 2153 BCRP 910 P-gp 1741	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 6.0	inconclusive [IC50 3.0901 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 44.0	inconclusive [IC50 30.9008 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 78.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 252.0	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 64.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 80.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 3.0	yes [IC50 1.3803 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 20.0	yes [IC50 10.1235 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 8.0	yes [IC50 3.8902 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 47.0	yes [IC50 36.2576 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 18 \| 251	inconclusive

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	substrate 9 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5337997#section=Biological-Test-Results Page: 42.0

PubMed

Title	Date	PubMed
Nifuroxazide inhibits survival of multiple myeloma cells by directly inhibiting STAT3.	2008-12-15	18824601

Patents

Sample Use Guides

In Vivo Use Guide

200 mg nifuroxazide 4 times a day in 2 to 4 doses.

Route of Administration: Oral

In Vitro Use Guide

2.5-20 uM nifuroxazide induces breast cancer cell apoptosis in a concentration-dependent manner.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:54:08 GMT 2025` Edited by `admin` on `Wed Apr 02 06:54:08 GMT 2025`
Record UNII	PM5LI0P38J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-759261

Preferred Name

English

NIFUROXAZIDE

Official Name

English

NIFUROXAZIDE [EP IMPURITY]

Common Name

English

NIFUROXAZIDE [MART.]

Common Name

English

Nifuroxazide [WHO-DD]

Common Name

English

NIFUROXAZIDE [EP MONOGRAPH]

Common Name

English

nifuroxazide [INN]

Common Name

English

P-HYDROXYBENZOIC ACID 5-NITROFURFURYLIDENE HYDRAZIDE

Common Name

English

SJ000287313

Code

English

RC-27109

Code

English

Classification Tree Code System Code

WHO-VATC

QA07AX03