U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H13N3O4S
Molecular Weight 295.314
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETYLSULFAMETHOXAZOLE

SMILES

CC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC2=NOC(C)=C2

InChI

InChIKey=GXPIUNZCALHVBA-UHFFFAOYSA-N
InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)

HIDE SMILES / InChI

Molecular Formula C12H13N3O4S
Molecular Weight 295.314
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

N-acetyl Sulfamethoxazole is a metabolite of sulfamethoxazole, an antibiotic with antiviral activity that can be detected in urine.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Response of Plasmodium falciparum to cotrimoxazole therapy: relationship with plasma drug concentrations and dihydrofolate reductase and dihydropteroate synthase genotypes.
2005-07
Metabolism by N-acetyltransferase 1 in vitro and in healthy volunteers: a prototype for targeted inhibition.
2004-12
Recognition of sulfamethoxazole and its reactive metabolites by drug-specific CD4+ T cells from allergic individuals.
2000-06-15

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:52:55 GMT 2025
Edited
by admin
on Mon Mar 31 19:52:55 GMT 2025
Record UNII
3I1988834Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETYLSULFAMETHOXAZOLE
JAN  
Common Name English
SULFAMETHOXAZOLE N4-ACETYLSULFAMETHOXAZOLE
MI  
Preferred Name English
SULFAMETHOXAZOLE IMPURITY A [EP IMPURITY]
Common Name English
ACETAMIDE, N-(4-(((5-METHYL-3-ISOXAZOLYL)AMINO)SULFONYL)PHENYL)-
Systematic Name English
SULFAMETHOXAZOLE RELATED COMPOUND A [USP-RS]
Common Name English
N-(4-(((5-METHYLISOXAZOL-3-YL)AMINO)SULFONYL)PHENYL)ACETAMIDE
Systematic Name English
ACETANILIDE, 4'-((5-METHYL-3-ISOXAZOLYL)SULFAMOYL)-
Systematic Name English
N-(4-((5-METHYLISOXAZOL-3-YL)SULFAMOYL)PHENYL)ACETAMIDE
Systematic Name English
SULFAMETHOXAZOLE N4-ACETYLSULFAMETHOXAZOLE [MI]
Common Name English
N4-ACETYLSULFAMETHOXAZOLE
Common Name English
ACETYLSULFAMETHOXAZOLE [JAN]
Common Name English
SULFAMETHOXAZOLE RELATED COMPOUND A
USP-RS  
Common Name English
N-4-ACETYLSULPHAMETHOXAZOLE
Common Name English
4'-ACETYL-3-SULFA-5-METHYLISOXAZOLE
Systematic Name English
Code System Code Type Description
PUBCHEM
65280
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
FDA UNII
3I1988834Q
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
ChEMBL
CHEMBL443
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
CAS
21312-10-7
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
CHEBI
31169
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
ECHA (EC/EINECS)
244-330-5
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
RS_ITEM_NUM
1631511
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID8049044
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY
MERCK INDEX
m10320
Created by admin on Mon Mar 31 19:52:55 GMT 2025 , Edited by admin on Mon Mar 31 19:52:55 GMT 2025
PRIMARY Merck Index
Related Record Type Details
PARENT -> METABOLITE
in slow acetylators, more parent drug is shunted toward the oxidative cytochrome P-450 pathway with the subsequent formation of the reactive hydroxylamine and nitroso metabolites. In a retrospective study, 90% of 21 patients who suffered from sulfa allergy were slow acetylators versus 55% in the general population, demonstrating an increased risk of ADRs to sulfonamides in slow acetylators.
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP