SULFISOXAZOLE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13N3O3S
Molecular Weight	267.304
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NOC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1C

InChI

InChIKey=NHUHCSRWZMLRLA-UHFFFAOYSA-N

InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C11H13N3O3S
Molecular Weight	267.304
Charge	0
Count

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=eb6ea746-3228-4969-8a26-653288662fd7
Curator's Comment: description was created based on several sources, including

Sulfisoxazole is a sulfonamide antibacterial antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfisoxazole acetyl in combination with erythromycin ethylsuccinate is used for treatment of ACUTE OTITIS MEDIA in children that is caused by susceptible strains of Haemophilus influenzae. Sulfisoxazole acetyl is a prodrug of sulfisoxazole. Acetyl group is added to make the drug poorly water soluble, and is hydrolyzed in vivo to the active drug. Sulfisoxazole and its acetylated metabolites are excreted primarily by the kidneys through glomerular filtration. Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7486915	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute otitis media 29 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=eb6ea746-3228-4969-8a26-653288662fd7	Curative		Approved 8583	ERYTHROMYCIN ETHYLSUCCINATE AND SULFISOXAZOLE ACETYL Approved Use For treatment of ACUTE OTITIS MEDIA in children that is caused by susceptible strains of Haemophilus influenzae. Launch Date 1988

C_max

Value	Dose	Co-administered	Analyte	Population
111.85 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3907496	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		SULFISOXAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
874.15 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3907496	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		SULFISOXAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3907496	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		SULFISOXAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
2 g single, intramuscular Dose: 2 g Route: intramuscular Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/5035788	healthy, 29-45 years Health Status: healthy Age Group: 29-45 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/5035788	Sources: https://pubmed.ncbi.nlm.nih.gov/5035788
2 g single, intravenous Dose: 2 g Route: intravenous Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/5035788	healthy, 29-45 years Health Status: healthy Age Group: 29-45 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/5035788	Sources: https://pubmed.ncbi.nlm.nih.gov/5035788
2 g single, oral Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/5035788	healthy, 29-45 years Health Status: healthy Age Group: 29-45 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/5035788	Sources: https://pubmed.ncbi.nlm.nih.gov/5035788
4 g 1 times / day multiple, oral Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14880425	unhealthy, 74 years Health Status: unhealthy Age Group: 74 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/14880425	Disc. AE: Granulocytopenia... AEs leading to discontinuation/dose reduction: Granulocytopenia Sources: https://pubmed.ncbi.nlm.nih.gov/14880425

AEs

AE	Significance	Dose	Population
Granulocytopenia	Disc. AE	4 g 1 times / day multiple, oral Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14880425	unhealthy, 74 years Health Status: unhealthy Age Group: 74 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/14880425

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 activator 150	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18505790/	weak
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes
CYP3A4 2633	activator 342 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4664062/	yes
PXR 51	activator 342 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4664062/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:102484	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102484
ChemicalBook	CB1495500	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1495500
eMolecules	511971	https://www.emolecules.com/cgi-bin/more?vid=511971
MolPort	MolPort-000-422-016	https://www.molport.com/shop/molecule-link/MolPort-000-422-016
Selleck Chemicals	Sulfisoxazole	http://www.selleckchem.com/products/Sulfisoxazole.html
ZINC	ZINC000096006009	http://zinc15.docking.org/substances/ZINC000096006009

PubMed

Title	Date	PubMed
Human metapneumovirus: an emerging respiratory pathogen.	2010-05	18584996
Changes in antimicrobial resistance among Salmonella enterica subspecies enterica serovar Pullorum isolates in China from 1962 to 2007.	2009-05-12	19128897
Antimicrobial susceptibility profiles of Salmonella enterica serotypes recovered from pens of commercial feedlot cattle using different types of composite samples.	2009-04	19219500
Associations between reported on-farm antimicrobial use practices and observed antimicrobial resistance in generic fecal Escherichia coli isolated from Alberta finishing swine farms.	2009-03-01	19041147
Condyloma acuminata in child end laser therapy: a case report.	2009-02-04	19193210
Antimicrobial resistance pattern of Salmonella serotypes isolated from food items and personnel in Addis Ababa, Ethiopia.	2009-02	18516698
Characterization of Salmonella isolates from retail foods based on serotyping, pulse field gel electrophoresis, antibiotic resistance and other phenotypic properties.	2009-01-31	19068272
Genotype, serotype, and antibiotic resistance of sorbitol-negative Escherichia coli isolates from feedlot cattle.	2009-01	19205460
Integron-mediated antibiotic resistance in Shiga toxin-producing Escherichia coli.	2009-01	19205459
Standards of medical care in diabetes--2009.	2009-01	19118286
Comparison of antimicrobial resistance in Escherichia coli, Staphylococcus aureus, and Listeria monocytogenes strains isolated from organic and conventional poultry meat.	2008-12	19244911
Contamination of chicken meat with Salmonella enterica Serovar Haardt with nalidixic acid resistance and reduced fluoroquinolone susceptibility.	2008-11	19047832
In vitro antimicrobial susceptibility of Streptococcus suis strains isolated from clinically healthy sows in China.	2008-10-15	18499362
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.	2008-09-26	18723177
Antimicrobial resistance and genetic characterization of fluoroquinolone resistance of Pseudomonas aeruginosa isolated from canine infections.	2008-09-18	18395369
Rescue of pulmonary hypertension with an oral sulfonamide antibiotic sulfisoxazole by endothelin receptor antagonistic actions.	2008-09	18971557
Antimicrobial activity of some sulfonamide derivatives on clinical isolates of Staphylococus aureus.	2008-08-20	18715512
Antimicrobial resistance and association with class 1 integrons in Escherichia coli isolated from turkey meat products.	2008-08	18724764
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine.	2008-08	18505790
Antimicrobial resistance in Salmonella enterica subspecies enterica serovar Dublin from dairy source calves in the central San Joaquin Valley, California (1998-2002).	2008-07	18599857
Safety of raw meat and shellfish in Vietnam: an analysis of Escherichia coli isolations for antibiotic resistance and virulence genes.	2008-06-10	18457892
Evaluation of gene expression in a single antibiotic exposure-derived isolate of Salmonella enterica typhimurium 14028 possessing resistance to multiple antibiotics.	2008-04	18407759
Integrated food chain surveillance system for Salmonella spp. in Mexico.	2008-03	18325258
Prevalence and characterization of Salmonella enterica serovar Weltevreden from imported seafood.	2008-02	17993374
New Ni(II)-sulfonamide complexes: synthesis, structural characterization and antibacterial properties. X-ray diffraction of [Ni(sulfisoxazole)2(H2O)4].2H2O and [Ni(sulfapyridine)2].	2008-02	17976730
Antimicrobial resistance in generic Escherichia coli isolated from swine fecal samples in 90 Alberta finishing farms.	2008	18505207
Pharmacokinetic of sulfisoxazole in aqueous humor after topical and subconjunctival application in dogs.	2007-11-15	19090302
Prevalence and antimicrobial resistance of Salmonella recovered from processed poultry.	2007-11	18044422
Phenotypic and genotypic antimicrobial resistance patterns of Escherichia coli isolated from dairy cows with mastitis.	2007-10-06	17544234
Multiple-locus variable-number tandem repeat analysis of Salmonella Enteritidis isolates from human and non-human sources using a single multiplex PCR.	2007-10	17692097
The first case of keratitis caused by Nocardia exalbida.	2007-10	17476571
Probiotic properties of Lactococcus lactis ssp. lactis HV219, isolated from human vaginal secretions.	2007-09	17714396
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007-08-03	17433345
Spectrum of eye disease caused by methicillin-resistant Staphylococcus aureus.	2007-08	17659970
Identification and molecular characterization of Salmonella spp. from unpasteurized orange juices and identification of new serotype Salmonella strain S. enterica serovar Tempe.	2007-08	17367687
A capillary zone electrophoresis method for the quantitative determination of hypoxoside in commercial formulations of African potato (Hypoxis hemerocallidea).	2007-07-13	17624891
Rituals, ceremonies and customs related to sacred trees with a special reference to the Middle East.	2007-07-09	17620122
Antimicrobial susceptibility of Salmonella isolated from various products, from 1999 to 2003.	2007-06	17612060
Genotypes, serotypes, and antibiotic resistance profiles of Salmonella isolated from commercial North Carolina turkey farms.	2007-06	17612059
Changes in antimicrobial susceptibility in a population of Escherichia coli isolated from feedlot cattle administered ceftiofur crystalline-free acid.	2007-05	17472449
The dominance of pandemic serovars of Vibrio parahaemolyticus in expatriates and sporadic cases of diarrhoea in Thailand, and a new emergent serovar (O3 : K46) with pandemic traits.	2007-05	17446282
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007-03-22	17373466
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007-03	17580695
Comparative investigation of prevalence and antimicrobial resistance of Salmonella between pasture and conventionally reared poultry.	2007-03	17461275
Multidrug-resistant Salmonella enterica serotype Typhimurium associated with pet rodents.	2007-01-04	17202452
The contribution of pharmacokinetic-pharmacodynamic modelling with Monte Carlo simulation to the development of susceptibility breakpoints for Neisseria meningitidis.	2007-01	17184285
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)].	2006-12-01	17180970
Quantitative determination of sulfonamide in meat by liquid chromatography-electrospray-mass spectrometry.	2001-12-24	18968466
Macrolide-antifol synergism in anti-Pneumocystis carinii therapeutics.	1991-11-01	1818149

Patents

Sample Use Guides

In Vivo Use Guide

Sulfisoxazole acetyl for oral suspension can be calculated based on the sulfisoxazole component (150 mg/kg/day to a maximum of 6 g/day). The total daily dose of sulfisoxazole acetyl for oral suspension should be administered in equally divided doses three or four times a day for 10 days

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:32 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:32 GMT 2025`
Record UNII	740T4C525W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFAFURAZOLE

Preferred Name

English

SULFISOXAZOLE

Common Name

English

N(SUP 1)-(3,4-DIMETHYL-5-ISOXAZOLYL)SULFANILAMIDE

Systematic Name

English

SULFAFURAZOLE [MART.]

Common Name

English

SULFISOXAZOLE [VANDF]

Common Name

English

SULPHAFURAZOLE

Common Name

English

SULFISOXAZOLE [ORANGE BOOK]

Common Name

English

SULFISOXAZOLE [MI]

Common Name

English

sulfafurazole [INN]

Common Name

English

SULFISOXAZOLE [USP-RS]

Common Name

English

SULFISOXAZOLE [HSDB]

Common Name

English

SULFISOXAZOLE [USP MONOGRAPH]

Common Name

English

NSC-13120

Code

English

SULFAFURAZOLE [EP MONOGRAPH]

Common Name

English

SULFAFURAZOLE [IARC]

Common Name

English

SULFISOXAZOLE [JAN]

Common Name

English

Sulfafurazole [WHO-DD]

Common Name

English

SULFISOXAZOLE [GREEN BOOK]

Common Name

English

AZO GANTRISIN COMPONENT SULFISOXAZOLE

Common Name

English

NSC-683536

Code

English

BENZENESULFONAMIDE, 4-AMINO-N-(3,4-DIMETHYL-5-ISOXAZOLYL)-

Systematic Name

English

GANTRISIN

Brand Name

English

Classification Tree Code System Code

NDF-RT

N0000175504