Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H12N4O3S |
Molecular Weight | 280.303 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CN=C(NS(=O)(=O)C2=CC=C(N)C=C2)N=C1
InChI
InChIKey=GPTONYMQFTZPKC-UHFFFAOYSA-N
InChI=1S/C11H12N4O3S/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,(H,13,14,15)
Molecular Formula | C11H12N4O3S |
Molecular Weight | 280.303 |
Charge | 0 |
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 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 |
|
[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 |
|
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate. | 2007 Nov |
|
Characterization of integrons-mediated antimicrobial resistance among Escherichia coli strains isolated from bovine mastitis. | 2008 Feb 5 |
|
On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil. | 2009 Aug 26 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14296029
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
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admin
on
Edited
Sat Dec 16 17:40:33 UTC 2023
by
admin
on
Sat Dec 16 17:40:33 UTC 2023
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Record UNII |
3L179F09D6
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Record Status |
Validated (UNII)
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J01ED04
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NCI_THESAURUS |
C29739
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757874
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C66568
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m10316
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3L179F09D6
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CHEMBL1200359
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SULFAMETOXYDIAZINE
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DB06821
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