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
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 n = 20 Health Status: unhealthy Condition: chronic urinary-tract infection Age Group: adult Sex: unknown Population Size: 20 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 n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 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 n = 6 Health Status: healthy Age Group: adult Sex: unknown Population Size: 6 Sources: |
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 n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 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 n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 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 n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Anticryptosporidial activity is associated with specific sulfonamides in immunosuppressed rats. | 1991 Apr |
|
| Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia. | 1996 Apr |
|
| Hydrogen bonding in sulfonamides. | 2001 Dec |
|
| Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey. | 2003 Jun |
|
| Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy. | 2004 Jun |
|
| [Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Complementary use of model-free and modelistic methods in the analysis of solid-state kinetics. | 2005 May 26 |
|
| Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2005 Sep-Oct |
|
| Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays. | 2006 Jun 28 |
|
| Development of an immunochromatographic lateral-flow test strip for rapid detection of sulfonamides in eggs and chicken muscles. | 2007 Mar 21 |
|
| Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS. | 2007 Nov |
|
| Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate. | 2007 Nov |
|
| ELISA for sulfonamides and its application for screening in water contamination. | 2008 Aug 13 |
|
| Characterization of integrons-mediated antimicrobial resistance among Escherichia coli strains isolated from bovine mastitis. | 2008 Feb 5 |
|
| Desolvation kinetics of sulfameter solvates. | 2008 Jun |
|
| [Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2008 May |
|
| Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking. | 2008 Sep 26 |
|
| On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil. | 2009 Aug 26 |
|
| [Investigation of sulfonamides and tetracyclines antibiotics in soils from various vegetable fields]. | 2009 Jun 15 |
|
| Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection. | 2009 Nov |
|
| Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer. | 2009 Nov 11 |
|
| Determination of 76 pharmaceutical drugs by liquid chromatography-tandem mass spectrometry in slaughterhouse wastewater. | 2009 Nov 20 |
|
| A new and simple method to determine trace levels of sulfonamides in honey by high performance liquid chromatography with fluorescence detection. | 2009 Oct 23 |
|
| N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(oxolan-2-ylamino)benzene-sulfonamide. | 2009 Oct 28 |
|
| Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents. | 2010 Apr 30 |
|
| Gene expression signature-based screening identifies new broadly effective influenza a antivirals. | 2010 Oct 4 |
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
37CB04ZYB9
Created by
admin on Sat Dec 16 16:53:54 UTC 2023 , Edited by admin on Sat Dec 16 16:53:54 UTC 2023
|
PRIMARY | |||
|
42628988
Created by
admin on Sat Dec 16 16:53:54 UTC 2023 , Edited by admin on Sat Dec 16 16:53:54 UTC 2023
|
PRIMARY | |||
|
18179-67-4
Created by
admin on Sat Dec 16 16:53:54 UTC 2023 , Edited by admin on Sat Dec 16 16:53:54 UTC 2023
|
PRIMARY | |||
|
DTXSID40171187
Created by
admin on Sat Dec 16 16:53:54 UTC 2023 , Edited by admin on Sat Dec 16 16:53:54 UTC 2023
|
PRIMARY |
SUBSTANCE RECORD
