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Details

Stereochemistry ACHIRAL
Molecular Formula C13H15N3O4S
Molecular Weight 309.3425
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFISOXAZOLE ACETYL

SMILES

Cc1c(C)noc1N(C(=O)C)S(=O)(=O)c2ccc(cc2)N

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 309.3425
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
111.85 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
874.15 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.15 h
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

Doses

DosePopulationAdverse events​
2 g single, intramuscular
Dose: 2 g
Route: intramuscular
Route: single
Dose: 2 g
Sources:
healthy, 29-45 years
n = 7
Health Status: healthy
Age Group: 29-45 years
Sex: M
Population Size: 7
Sources:
2 g single, intravenous
Dose: 2 g
Route: intravenous
Route: single
Dose: 2 g
Sources:
healthy, 29-45 years
n = 7
Health Status: healthy
Age Group: 29-45 years
Sex: M
Population Size: 7
Sources:
2 g single, oral
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, 29-45 years
n = 7
Health Status: healthy
Age Group: 29-45 years
Sex: M
Population Size: 7
Sources:
4 g 1 times / day multiple, oral
Dose: 4 g, 1 times / day
Route: oral
Route: multiple
Dose: 4 g, 1 times / day
Sources:
unhealthy, 74 years
n = 1
Health Status: unhealthy
Age Group: 74 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Granulocytopenia...
AEs leading to
discontinuation/dose reduction:
Granulocytopenia
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 74 years
n = 1
Health Status: unhealthy
Age Group: 74 years
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Macrolide-antifol synergism in anti-Pneumocystis carinii therapeutics.
1991 Nov-Dec
The prevalence of Salmonella spp. in bovine faecal, rumen and carcass samples at a commercial abattoir.
2003
Antimicrobial susceptibilities of Listeria monocytogenes strains isolated from 2000 to 2002 in Poland.
2004
Salmonella Typhimurium outbreak associated with veterinary clinic.
2004 Dec
Adenoidectomy versus chemoprophylaxis and placebo for recurrent acute otitis media in children aged under 2 years: randomised controlled trial.
2004 Feb 28
[Comparison of multidrug-resistant Salmonella enterica serovar Newport isolates from a patient and sewages in Fukui Prefecture].
2005 Apr
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
Antimicrobial resistance of Shiga toxin (verotoxin)-producing Escherichia coli O157:H7 and non-O157 strains isolated from humans, cattle, sheep and food in Spain.
2005 Aug
Heme impairs allosterically drug binding to human serum albumin Sudlow's site I.
2005 Aug 26
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Helicobacter pylori and histopathological changes of gastric mucosa in Uganda population with varying prevalence of stomach cancer.
2005 Sep
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
Toxicity of polymyxins: a systematic review of the evidence from old and recent studies.
2006 Feb
Multidrug resistance and distribution of Salmonella serovars in slaughtered pigs.
2006 Feb
Antimicrobial resistance of Escherichia coli O157 from cattle in Korea.
2006 Jan 15
Sulfisoxazole, an endothelin receptor antagonist, protects retinal neurones from insults of ischemia/reperfusion or lipopolysaccharide.
2006 Jun
Measurement of unbound bilirubin by the peroxidase test using Zone Fluidics.
2006 Mar
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.
2006 Oct 13
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
Spectrum of eye disease caused by methicillin-resistant Staphylococcus aureus.
2007 Aug
Rituals, ceremonies and customs related to sacred trees with a special reference to the Middle East.
2007 Jul 9
Antimicrobial susceptibility of Salmonella isolated from various products, from 1999 to 2003.
2007 Jun
Genotypes, serotypes, and antibiotic resistance profiles of Salmonella isolated from commercial North Carolina turkey farms.
2007 Jun
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].
2007 Mar
Comparative investigation of prevalence and antimicrobial resistance of Salmonella between pasture and conventionally reared poultry.
2007 Mar
Prevalence and antimicrobial resistance of Salmonella recovered from processed poultry.
2007 Nov
A capillary zone electrophoresis method for the quantitative determination of hypoxoside in commercial formulations of African potato (Hypoxis hemerocallidea).
2007 Nov-Dec
Multiple-locus variable-number tandem repeat analysis of Salmonella Enteritidis isolates from human and non-human sources using a single multiplex PCR.
2007 Oct
The first case of keratitis caused by Nocardia exalbida.
2007 Oct
Phenotypic and genotypic antimicrobial resistance patterns of Escherichia coli isolated from dairy cows with mastitis.
2007 Oct 6
Probiotic properties of Lactococcus lactis ssp. lactis HV219, isolated from human vaginal secretions.
2007 Sep
Antimicrobial resistance in generic Escherichia coli isolated from swine fecal samples in 90 Alberta finishing farms.
2008
Evaluation of gene expression in a single antibiotic exposure-derived isolate of Salmonella enterica typhimurium 14028 possessing resistance to multiple antibiotics.
2008 Apr
Antimicrobial resistance and association with class 1 integrons in Escherichia coli isolated from turkey meat products.
2008 Aug
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine.
2008 Aug
Antimicrobial activity of some sulfonamide derivatives on clinical isolates of Staphylococus aureus.
2008 Aug 20
Comparison of antimicrobial resistance in Escherichia coli, Staphylococcus aureus, and Listeria monocytogenes strains isolated from organic and conventional poultry meat.
2008 Dec
Prevalence and characterization of Salmonella enterica serovar Weltevreden from imported seafood.
2008 Feb
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
Antimicrobial resistance in Salmonella enterica subspecies enterica serovar Dublin from dairy source calves in the central San Joaquin Valley, California (1998-2002).
2008 Jul
Safety of raw meat and shellfish in Vietnam: an analysis of Escherichia coli isolations for antibiotic resistance and virulence genes.
2008 Jun 10
In vitro antimicrobial susceptibility of Streptococcus suis strains isolated from clinically healthy sows in China.
2008 Oct 15
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.
2008 Sep 26
Antimicrobial susceptibility profiles of Salmonella enterica serotypes recovered from pens of commercial feedlot cattle using different types of composite samples.
2009 Apr
Antimicrobial resistance pattern of Salmonella serotypes isolated from food items and personnel in Addis Ababa, Ethiopia.
2009 Feb
Condyloma acuminata in child end laser therapy: a case report.
2009 Feb 4
Genotype, serotype, and antibiotic resistance of sorbitol-negative Escherichia coli isolates from feedlot cattle.
2009 Jan
Integron-mediated antibiotic resistance in Shiga toxin-producing Escherichia coli.
2009 Jan
Changes in antimicrobial resistance among Salmonella enterica subspecies enterica serovar Pullorum isolates in China from 1962 to 2007.
2009 May 12
Human metapneumovirus: an emerging respiratory pathogen.
2010 May
Patents

Sample Use Guides

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
Curator's Comment:: In vitro studies provided support for the protective effect of sulfisoxazole. Here, it was clearly shown that sulfisoxazole attenuated the elevation of nitric oxide (deduced by measuring nitrite) and the reduction in numbers of GABA-containing neurones caused by LPS
Unknown
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:02:32 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:32 UTC 2021
Record UNII
WBT5QH3KED
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFISOXAZOLE ACETYL
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
SULFAFURAZOLE ACETYL
WHO-DD  
Common Name English
ACETYLSULFISOXAZOLE
JAN  
Common Name English
ACETYL SULFAFURAZOLE
MART.  
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
MI  
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
SULFAFURAZOLE ACETYL [WHO-DD]
Common Name English
PEDIAZOLE COMPONENT SULFISOXAZOLE ACETYL
Common Name English
SULFISOXAZOLE ACETYL COMPONENT OF ERYZOLE
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
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C47741
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
DRUG CENTRAL
4458
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
CAS
80-74-0
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
MESH
C005387
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
FDA UNII
WBT5QH3KED
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
EVMPD
SUB04623MIG
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
PUBCHEM
6662
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
MERCK INDEX
M10352
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
201-305-3
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
RXCUI
40595
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB14033
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
USP_CATALOG
1639003
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY USP-RS
EPA CompTox
80-74-0
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200910
Created by admin on Fri Jun 25 21:02:32 UTC 2021 , Edited by admin on Fri Jun 25 21:02:32 UTC 2021
PRIMARY
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