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 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 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 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
Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep.	2001 Mar	11282267
Cholera in the United States, 1995-2000: trends at the end of the twentieth century.	2001 Sep 15	11517445
Trends in antimicrobial resistance of Salmonella isolated from animals, foods of animal origin, and the environment of animal production in Canada, 1994-1997.	2001 Summer	11442347
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.	2002 Jun	12019133
The use of sequential studies in a salmonellosis outbreak linked to continental custard cakes.	2002 Oct	12403104
The prevalence of Salmonella spp. in bovine faecal, rumen and carcass samples at a commercial abattoir.	2003	12631205
Antimicrobial resistance of Escherichia coli strains isolated from urine of women with cystitis or pyelonephritis and feces of dogs and healthy humans.	2004 Aug 1	15328711
Salmonella Typhimurium outbreak associated with veterinary clinic.	2004 Dec	15663875
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
Salmonella enterica isolates from faeces of domestic reptiles and a study of their antimicrobial in vitro sensitivity.	2005 Apr	15563917
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
Antimicrobial susceptibilities of Salmonella isolates obtained from layer chicken houses on a commercial egg-producing farm in Japan, 1997 to 2002.	2005 Oct	16245703
Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)].	2006 Dec 1	17180970
Multidrug resistance and distribution of Salmonella serovars in slaughtered pigs.	2006 Feb	16460353
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
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
Antimicrobial susceptibility of Salmonella isolated from various products, from 1999 to 2003.	2007 Jun	17612060
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007 Mar	17580695
Changes in antimicrobial susceptibility in a population of Escherichia coli isolated from feedlot cattle administered ceftiofur crystalline-free acid.	2007 May	17472449
Antimicrobial resistance in generic Escherichia coli isolated from swine fecal samples in 90 Alberta finishing farms.	2008	18505207
Prevalence and characterization of Salmonella enterica serovar Weltevreden from imported seafood.	2008 Feb	17993374
Contamination of chicken meat with Salmonella enterica Serovar Haardt with nalidixic acid resistance and reduced fluoroquinolone susceptibility.	2008 Nov	19047832
Antimicrobial susceptibility profiles of Salmonella enterica serotypes recovered from pens of commercial feedlot cattle using different types of composite samples.	2009 Apr	19219500
Genotype, serotype, and antibiotic resistance of sorbitol-negative Escherichia coli isolates from feedlot cattle.	2009 Jan	19205460
Characterization of Salmonella isolates from retail foods based on serotyping, pulse field gel electrophoresis, antibiotic resistance and other phenotypic properties.	2009 Jan 31	19068272
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:55 GMT 2023`
Record UNII	740T4C525W
Record Status	`Validated (UNII)`
Record Version

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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