Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H11N4O3S.Na |
| Molecular Weight | 302.285 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].COC1=CN=C([N-]S(=O)(=O)C2=CC=C(N)C=C2)N=C1
InChI
InChIKey=LBCSHRNIIWKVRX-UHFFFAOYSA-N
InChI=1S/C11H11N4O3S.Na/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10;/h2-7H,12H2,1H3;/q-1;+1
| Molecular Formula | C11H11N4O3S |
| Molecular Weight | 279.295 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.sigmaaldrich.com/catalog/product/sigma/s0383?lang=es®ion=ES
http://www.medchemexpress.com/sulfameter.html
Curator's Comment: description was created based on several sources, including:
http://www.sigmaaldrich.com/catalog/product/sigma/s0383?lang=es®ion=ES
http://www.medchemexpress.com/sulfameter.html
Sulfametoxydiazine (INN) or sulfamethoxydiazine (USAN: sulfameter) is a long-acting sulfonamide antibacterial, shows bacteriostatic effects against Gram positive and Gram negative bacteria in vivo. It is used as a leprostatic agent and in the treatment of urinary tract infections. Orally active. Sulfonamides block the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfonamides are competitive inhibitors of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. Sulfameter is a dihydrofolate reductase (DHFR) inhibitor. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
44.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5072410/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETER plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1599 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5072410/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETER plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5072410/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETER plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
250 mg/kg 1 times / day steady, oral Recommended Dose: 250 mg/kg, 1 times / day Route: oral Route: steady Dose: 250 mg/kg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
|
500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Nasal stuffiness, Edema lip... AEs leading to discontinuation/dose reduction: Nasal stuffiness (2 patients) Sources: Edema lip (1 patient) Leukopenia (1 patient) |
2 g single, oral Studied dose |
healthy, adult |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Edema lip | 1 patient Disc. AE |
500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
| Leukopenia | 1 patient Disc. AE |
500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
| Nasal stuffiness | 2 patients Disc. AE |
500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Gene expression signature-based screening identifies new broadly effective influenza a antivirals. | 2010-10-04 |
|
| Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents. | 2010-04-30 |
|
| Determination of 76 pharmaceutical drugs by liquid chromatography-tandem mass spectrometry in slaughterhouse wastewater. | 2009-11-20 |
|
| Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer. | 2009-11-11 |
|
| Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection. | 2009-11 |
|
| N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(oxolan-2-ylamino)benzene-sulfonamide. | 2009-10-28 |
|
| A new and simple method to determine trace levels of sulfonamides in honey by high performance liquid chromatography with fluorescence detection. | 2009-10-23 |
|
| On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil. | 2009-08-26 |
|
| [Investigation of sulfonamides and tetracyclines antibiotics in soils from various vegetable fields]. | 2009-06-15 |
|
| Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking. | 2008-09-26 |
|
| ELISA for sulfonamides and its application for screening in water contamination. | 2008-08-13 |
|
| Desolvation kinetics of sulfameter solvates. | 2008-06 |
|
| [Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2008-05 |
|
| Characterization of integrons-mediated antimicrobial resistance among Escherichia coli strains isolated from bovine mastitis. | 2008-02-05 |
|
| Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS. | 2007-11 |
|
| Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate. | 2007-11 |
|
| Development of an immunochromatographic lateral-flow test strip for rapid detection of sulfonamides in eggs and chicken muscles. | 2007-03-21 |
|
| Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays. | 2006-06-28 |
|
| Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2006-01-03 |
|
| [Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005-07 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Complementary use of model-free and modelistic methods in the analysis of solid-state kinetics. | 2005-05-26 |
|
| Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy. | 2004-06 |
|
| Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey. | 2003-06 |
|
| Hydrogen bonding in sulfonamides. | 2001-12 |
|
| Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia. | 1996-04 |
|
| Anticryptosporidial activity is associated with specific sulfonamides in immunosuppressed rats. | 1991-04 |
Patents
Sample Use Guides
Loading dose first-day only (single dose): 1500 mg (3 tablets)
Daily maintenance (single dose at 24 hour intervals): 500 mg (1 tablet).
Route of Administration:
Oral
Titrations of antibacterial activity were carried out by making twofold serial dilutions dilutions of plasma or serum and adding an equal volume (0.5 ml.) of a 10-5 dilution of an overnight culture of a strain of Escherichia coli which had been isolated from the peritoneal fluid of a patient with peritonitis and which was consistently sensitive to 0.30 mg. of sulfamethoxydiazine per 100 ml. of broth. Study of antibacterial titers showed that at 1: 64 the sulfonamide concentrations varied from 7 to 14 mg. per 100 ml
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:29:59 GMT 2025
by
admin
on
Wed Apr 02 08:29:59 GMT 2025
|
| Record UNII |
37CB04ZYB9
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
37CB04ZYB9
Created by
admin on Wed Apr 02 08:29:59 GMT 2025 , Edited by admin on Wed Apr 02 08:29:59 GMT 2025
|
PRIMARY | |||
|
42628988
Created by
admin on Wed Apr 02 08:29:59 GMT 2025 , Edited by admin on Wed Apr 02 08:29:59 GMT 2025
|
PRIMARY | |||
|
18179-67-4
Created by
admin on Wed Apr 02 08:29:59 GMT 2025 , Edited by admin on Wed Apr 02 08:29:59 GMT 2025
|
PRIMARY | |||
|
DTXSID40171187
Created by
admin on Wed Apr 02 08:29:59 GMT 2025 , Edited by admin on Wed Apr 02 08:29:59 GMT 2025
|
PRIMARY |