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

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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute otitis media 28 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=eb6ea746-3228-4969-8a26-653288662fd7	Curative		Approved 8429	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 5.8000317E11

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 n = 7 Health Status: healthy Age Group: 29-45 years Sex: M Population Size: 7 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 n = 7 Health Status: healthy Age Group: 29-45 years Sex: M Population Size: 7 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 n = 7 Health Status: healthy Age Group: 29-45 years Sex: M Population Size: 7 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 n = 1 Health Status: unhealthy Age Group: 74 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 74 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14880425

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781 activator 80	inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911 CYP2C19 1478

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/18505790/	weak
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	yes
CYP3A4 1925	activator 214 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4664062/	yes
PXR 46	activator 214 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
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
eMolecules	511971	https://www.emolecules.com/cgi-bin/more?vid=511971

PubMed

Title	Date	PubMed
Macrolide-antifol synergism in anti-Pneumocystis carinii therapeutics.	1991 Nov-Dec	1818149
Quantitative determination of sulfonamide in meat by liquid chromatography-electrospray-mass spectrometry.	2001 Dec 24	18968466
Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)].	2006 Dec 1	17180970
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
Spectrum of eye disease caused by methicillin-resistant Staphylococcus aureus.	2007 Aug	17659970
Identification and molecular characterization of Salmonella spp. from unpasteurized orange juices and identification of new serotype Salmonella strain S. enterica serovar Tempe.	2007 Aug	17367687
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007 Aug 3	17433345
The contribution of pharmacokinetic-pharmacodynamic modelling with Monte Carlo simulation to the development of susceptibility breakpoints for Neisseria meningitidis.	2007 Jan	17184285
Multidrug-resistant Salmonella enterica serotype Typhimurium associated with pet rodents.	2007 Jan 4	17202452
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007 Jan-Feb	17373466
Rituals, ceremonies and customs related to sacred trees with a special reference to the Middle East.	2007 Jul 9	17620122
Antimicrobial susceptibility of Salmonella isolated from various products, from 1999 to 2003.	2007 Jun	17612060
Genotypes, serotypes, and antibiotic resistance profiles of Salmonella isolated from commercial North Carolina turkey farms.	2007 Jun	17612059
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007 Mar	17580695
Comparative investigation of prevalence and antimicrobial resistance of Salmonella between pasture and conventionally reared poultry.	2007 Mar	17461275
Changes in antimicrobial susceptibility in a population of Escherichia coli isolated from feedlot cattle administered ceftiofur crystalline-free acid.	2007 May	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 May	17446282
Prevalence and antimicrobial resistance of Salmonella recovered from processed poultry.	2007 Nov	18044422
Pharmacokinetic of sulfisoxazole in aqueous humor after topical and subconjunctival application in dogs.	2007 Nov 15	19090302
A capillary zone electrophoresis method for the quantitative determination of hypoxoside in commercial formulations of African potato (Hypoxis hemerocallidea).	2007 Nov-Dec	17624891
Multiple-locus variable-number tandem repeat analysis of Salmonella Enteritidis isolates from human and non-human sources using a single multiplex PCR.	2007 Oct	17692097
The first case of keratitis caused by Nocardia exalbida.	2007 Oct	17476571
Phenotypic and genotypic antimicrobial resistance patterns of Escherichia coli isolated from dairy cows with mastitis.	2007 Oct 6	17544234
Probiotic properties of Lactococcus lactis ssp. lactis HV219, isolated from human vaginal secretions.	2007 Sep	17714396
Antimicrobial resistance in generic Escherichia coli isolated from swine fecal samples in 90 Alberta finishing farms.	2008	18505207
Evaluation of gene expression in a single antibiotic exposure-derived isolate of Salmonella enterica typhimurium 14028 possessing resistance to multiple antibiotics.	2008 Apr	18407759
Antimicrobial resistance and association with class 1 integrons in Escherichia coli isolated from turkey meat products.	2008 Aug	18724764
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine.	2008 Aug	18505790
Antimicrobial activity of some sulfonamide derivatives on clinical isolates of Staphylococus aureus.	2008 Aug 20	18715512
Comparison of antimicrobial resistance in Escherichia coli, Staphylococcus aureus, and Listeria monocytogenes strains isolated from organic and conventional poultry meat.	2008 Dec	19244911
Prevalence and characterization of Salmonella enterica serovar Weltevreden from imported seafood.	2008 Feb	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 Feb	17976730
Antimicrobial resistance in Salmonella enterica subspecies enterica serovar Dublin from dairy source calves in the central San Joaquin Valley, California (1998-2002).	2008 Jul	18599857
Safety of raw meat and shellfish in Vietnam: an analysis of Escherichia coli isolations for antibiotic resistance and virulence genes.	2008 Jun 10	18457892
Integrated food chain surveillance system for Salmonella spp. in Mexico.	2008 Mar	18325258
Contamination of chicken meat with Salmonella enterica Serovar Haardt with nalidixic acid resistance and reduced fluoroquinolone susceptibility.	2008 Nov	19047832
In vitro antimicrobial susceptibility of Streptococcus suis strains isolated from clinically healthy sows in China.	2008 Oct 15	18499362
Rescue of pulmonary hypertension with an oral sulfonamide antibiotic sulfisoxazole by endothelin receptor antagonistic actions.	2008 Sep	18971557
Antimicrobial resistance and genetic characterization of fluoroquinolone resistance of Pseudomonas aeruginosa isolated from canine infections.	2008 Sep 18	18395369
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.	2008 Sep 26	18723177
Antimicrobial susceptibility profiles of Salmonella enterica serotypes recovered from pens of commercial feedlot cattle using different types of composite samples.	2009 Apr	19219500
Antimicrobial resistance pattern of Salmonella serotypes isolated from food items and personnel in Addis Ababa, Ethiopia.	2009 Feb	18516698
Condyloma acuminata in child end laser therapy: a case report.	2009 Feb 4	19193210
Genotype, serotype, and antibiotic resistance of sorbitol-negative Escherichia coli isolates from feedlot cattle.	2009 Jan	19205460
Integron-mediated antibiotic resistance in Shiga toxin-producing Escherichia coli.	2009 Jan	19205459
Standards of medical care in diabetes--2009.	2009 Jan	19118286
Characterization of Salmonella isolates from retail foods based on serotyping, pulse field gel electrophoresis, antibiotic resistance and other phenotypic properties.	2009 Jan 31	19068272
Associations between reported on-farm antimicrobial use practices and observed antimicrobial resistance in generic fecal Escherichia coli isolated from Alberta finishing swine farms.	2009 Mar 1	19041147
Changes in antimicrobial resistance among Salmonella enterica subspecies enterica serovar Pullorum isolates in China from 1962 to 2007.	2009 May 12	19128897
Human metapneumovirus: an emerging respiratory pathogen.	2010 May	18584996

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

Name

Type

Language

SULFISOXAZOLE

Common Name

English

SULFAFURAZOLE

Official 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

SULFISOXAZOLE COMPONENT OF AZO GANTRISIN

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175504