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 |
|---|---|---|
| Hydrogen bonding in sulfonamides. | 2001 Dec |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays. | 2006 Jun 28 |
|
| [Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2008 May |
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
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37CB04ZYB9
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42628988
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18179-67-4
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DTXSID40171187
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SUBSTANCE RECORD
