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 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
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.	2002 Jun	12019133
Survey of residual tetracycline antibiotics and sulfa drugs in kidneys of diseased animals in the Aichi Prefecture, Japan (1995-1999).	2003 May-Jun	12852565
The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-beta-cyclodextrin.	2003 Nov	14592694
Adenoidectomy versus chemoprophylaxis and placebo for recurrent acute otitis media in children aged under 2 years: randomised controlled trial.	2004 Feb 28	14769785
Enterotoxin-producing Escherichia coli O169:H41, United States.	2004 Mar	15109427
Effect of ibuprofen on bilirubin-albumin binding.	2004 Mar	15001951
Heme impairs allosterically drug binding to human serum albumin Sudlow's site I.	2005 Aug 26	16004963
Antimicrobial-drug susceptibility of human and animal Salmonella typhimurium, Minnesota, 1997-2003.	2005 Dec	16485477
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Toxicity of polymyxins: a systematic review of the evidence from old and recent studies.	2006 Feb	16507149
Sulfisoxazole, an endothelin receptor antagonist, protects retinal neurones from insults of ischemia/reperfusion or lipopolysaccharide.	2006 Jun	16464516
Low-level fluoroquinolone resistance among Campylobacter jejuni isolates in Australia.	2006 May 15	16619147
Multiwalled carbon nanotubes as sorbent for on-line coupling of solid-phase extraction to high-performance liquid chromatography for simultaneous determination of 10 sulfonamides in eggs and pork.	2006 Sep 15	16820156
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
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
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
Phenotypic and genotypic antimicrobial resistance patterns of Escherichia coli isolated from dairy cows with mastitis.	2007 Oct 6	17544234
Antimicrobial activity of some sulfonamide derivatives on clinical isolates of Staphylococus aureus.	2008 Aug 20	18715512
Prevalence and characterization of Salmonella enterica serovar Weltevreden from imported seafood.	2008 Feb	17993374
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
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
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

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