SULFISOXAZOLE ACETYL

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H15N3O4S
Molecular Weight	309.341
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N(C1=C(C)C(C)=NO1)S(=O)(=O)C2=CC=C(N)C=C2

InChI

InChIKey=JFNWFXVFBDDWCX-UHFFFAOYSA-N

InChI=1S/C13H15N3O4S/c1-8-9(2)15-20-13(8)16(10(3)17)21(18,19)12-6-4-11(14)5-7-12/h4-7H,14H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C13H15N3O4S
Molecular Weight	309.341
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
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
Antimicrobial resistance in Salmonella enterica serovars Enteritidis and Typhimurium isolated from animals in Korea: comparison of phenotypic and genotypic resistance characterization.	2002 May 24	11955779
Phenotypic and genotypic characterization of food animal isolates of Salmonella with reduced sensitivity to ciprofloxacin.	2002 Winter	12523636
The prevalence of Salmonella spp. in bovine faecal, rumen and carcass samples at a commercial abattoir.	2003	12631205
Reflections on errors in neonatology: II. The "Heroic" years, 1950 to 1970.	2003 Mar	12673267
Survey of residual tetracycline antibiotics and sulfa drugs in kidneys of diseased animals in the Aichi Prefecture, Japan (1995-1999).	2003 May-Jun	12852565
Antimicrobial susceptibilities of Listeria monocytogenes strains isolated from 2000 to 2002 in Poland.	2004	15790078
Chemometric and derivative methods as flexible spectrophotometric approaches for dissolution and assaying tests in multicomponent tablets.	2004 Aug	15262532
Salmonella Typhimurium outbreak associated with veterinary clinic.	2004 Dec	15663875
Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclic groups.	2004 Jul 15	15298203
Effect of ibuprofen on bilirubin-albumin binding.	2004 Mar	15001951
Characterization of sulfonamides by flow injection and liquid chromatography-electrospray ionization-mass spectrometry after online photoderivatization.	2004 Nov-Dec	15768836
CTX-M and SHV-12 beta-lactamases are the most common extended-spectrum enzymes in clinical isolates of Escherichia coli and Klebsiella pneumoniae collected from 3 university hospitals within Korea.	2005 Apr 1	15796985
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
Determination of pKa values by capillary zone electrophoresis with a dynamic coating procedure.	2005 Nov	16342805
Antimicrobial susceptibilities of Salmonella isolates obtained from layer chicken houses on a commercial egg-producing farm in Japan, 1997 to 2002.	2005 Oct	16245703
Helicobacter pylori and histopathological changes of gastric mucosa in Uganda population with varying prevalence of stomach cancer.	2005 Sep	16245994
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
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
Antimicrobial resistance of Escherichia coli O157 from cattle in Korea.	2006 Jan 15	16300850
Changes in antimicrobial susceptibility of Actinobacillus pleuropneumoniae isolated from pigs in Spain during the last decade.	2006 Jun 15	16431040
On the typology and the worship status of sacred trees with a special reference to the Middle East.	2006 May 15	16700917
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
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
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
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
[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
A capillary zone electrophoresis method for the quantitative determination of hypoxoside in commercial formulations of African potato (Hypoxis hemerocallidea).	2007 Nov-Dec	17624891
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
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
In vitro antimicrobial susceptibility of Streptococcus suis strains isolated from clinically healthy sows in China.	2008 Oct 15	18499362
Antimicrobial susceptibility profiles of Salmonella enterica serotypes recovered from pens of commercial feedlot cattle using different types of composite samples.	2009 Apr	19219500
Condyloma acuminata in child end laser therapy: a case report.	2009 Feb 4	19193210
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:42 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:42 GMT 2023`
Record UNII	WBT5QH3KED
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFISOXAZOLE ACETYL

Common Name

English

SULFAFURAZOLE ACETYL

Common Name

English

ACETYLSULFISOXAZOLE

Common Name

English

ACETYL SULFAFURAZOLE

Common Name

English

ERYZOLE COMPONENT SULFISOXAZOLE ACETYL

Common Name

English

SULFISOXAZOLE ACETYL COMPONENT OF ILOSONE SULFA

Common Name

English

N-(3,4-Dimethyl-5-isoxazolyl)-N-sulfanilylacetamide

Systematic Name

English

ACETAMIDE, N-((4-AMINOPHENYL)SULFONYL)-N-(3,4-DIMETHYL-5-ISOXAZOLYL)-

Systematic Name

English

SULFISOXAZOLE ACETYL [USP MONOGRAPH]

Common Name

English

ACETYLSULFAFURAZOLE

Common Name

English

ACETYL SULFISOXAZOLE

Common Name

English

ACETYL SULFISOXAZOLE [MI]

Common Name

English

ACETYL SULFAFURAZOLE [MART.]

Common Name

English

SULFISOXIZOLE ACETYL

Common Name

English

ACETYLSULFISOXAZOLE [JAN]

Common Name

English

SULFISOXAZOLE ACETYL [VANDF]

Common Name

English

ILOSONE SULFA COMPONENT SULFISOXAZOLE ACETYL

Common Name

English

NSC-759138

Code

English

PEDIAZOLE COMPONENT SULFISOXAZOLE ACETYL

Common Name

English

SULFISOXAZOLE ACETYL COMPONENT OF ERYZOLE

Common Name

English

Sulfafurazole acetyl [WHO-DD]

Common Name

English

SULFISOXAZOLE ACETYL [USP-RS]

Common Name

English

SULFISOXAZOLE ACETYL COMPONENT OF PEDIAZOLE

Common Name

English

SULFISOXAZOLE ACETYL [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739