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=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)C=C1
InChI
InChIKey=VLYWMPOKSSWJAL-UHFFFAOYSA-N
InChI=1S/C11H12N4O3S/c1-18-11-7-6-10(13-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/13783165Curator's Comment: description was created based on several sources, including
DOI: 10.1002/0471238961.1921120606152505.a01
http://www.ncbi.nlm.nih.gov/pubmed/7486915
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13783165
Curator's Comment: description was created based on several sources, including
DOI: 10.1002/0471238961.1921120606152505.a01
http://www.ncbi.nlm.nih.gov/pubmed/7486915
Sulfamethoxypyridazine is a sulfonamide antibacterial with a broad spector of activity. It acts by inhibiting the enzyme dihydropteroate synthetase (DHPS), required for the synthesis of nucleic acids and microbial cells.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: bacterial dihydropteroate synthetase Sources: http://www.ncbi.nlm.nih.gov/pubmed/7486915 |
0.017 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.75 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6081878/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETHOXYPYRIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
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0.85 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6081878/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETHOXYPYRIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38 h |
SULFAMETHOXYPYRIDAZINE unknown | Homo sapiens |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.5% |
SULFAMETHOXYPYRIDAZINE plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
3 g 1 times / week multiple, oral Highest studied dose Dose: 3 g, 1 times / week Route: oral Route: multiple Dose: 3 g, 1 times / week Sources: Page: p.507 |
unhealthy, 5 - 15 n = 6 Health Status: unhealthy Condition: Rheumatic fever Age Group: 5 - 15 Sex: M+F Population Size: 6 Sources: Page: p.507 |
Disc. AE: Skin rash... AEs leading to discontinuation/dose reduction: Skin rash (33%) Sources: Page: p.507 |
1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.688 |
unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: Page: p.688 |
Disc. AE: Skin rash, Itching... AEs leading to discontinuation/dose reduction: Skin rash (severe) Sources: Page: p.688Itching (severe) Hepatitis (acute) Fever |
0.5 g 1 times / day multiple, oral Studied dose Dose: 0.5 g, 1 times / day Route: oral Route: multiple Dose: 0.5 g, 1 times / day Sources: Page: p.40 |
unhealthy, 89 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 89 Sex: F Population Size: 1 Sources: Page: p.40 |
Disc. AE: Exfoliative dermatitis... AEs leading to discontinuation/dose reduction: Exfoliative dermatitis (grade 5) Sources: Page: p.40 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Skin rash | 33% Disc. AE |
3 g 1 times / week multiple, oral Highest studied dose Dose: 3 g, 1 times / week Route: oral Route: multiple Dose: 3 g, 1 times / week Sources: Page: p.507 |
unhealthy, 5 - 15 n = 6 Health Status: unhealthy Condition: Rheumatic fever Age Group: 5 - 15 Sex: M+F Population Size: 6 Sources: Page: p.507 |
Fever | Disc. AE | 1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.688 |
unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: Page: p.688 |
Hepatitis | acute Disc. AE |
1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.688 |
unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: Page: p.688 |
Itching | severe Disc. AE |
1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.688 |
unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: Page: p.688 |
Skin rash | severe Disc. AE |
1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.688 |
unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: Page: p.688 |
Exfoliative dermatitis | grade 5 Disc. AE |
0.5 g 1 times / day multiple, oral Studied dose Dose: 0.5 g, 1 times / day Route: oral Route: multiple Dose: 0.5 g, 1 times / day Sources: Page: p.40 |
unhealthy, 89 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 89 Sex: F Population Size: 1 Sources: Page: p.40 |
PubMed
Title | Date | PubMed |
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In vitro activity of antimicrobial agents against mycobacteria. | 1988 |
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Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole. | 1988 Dec |
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Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. | 1995 Aug |
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Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia. | 1996 Apr |
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Evaluation of sulfa drugs against recombinant Pneumocystis carinii dihydropteroate synthetase and in vivo. | 1996 Sep-Oct |
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Simultaneous determination of binary mixtures of trimethoprim and sulfamethoxazole or sulphamethoxypyridazine by the bivariate calibration spectrophotometric method. | 2002 Aug 22 |
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In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
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Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey. | 2003 Jun |
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Determination of some sulfonamides and trimethoprim in chicken, fish muscle and eggs by liquid chromatography-tandem mass spectrometry. | 2004 Apr-Jun |
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Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection. | 2004 Aug 20 |
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Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy. | 2004 Jun |
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Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection. | 2004 Sep 8 |
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Sulfamethoxypyridazine-responsive pemphigoid nodularis: a report of two cases. | 2005 Aug |
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[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
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Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2005 Sep-Oct |
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Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection. | 2006 Aug 18 |
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Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays. | 2006 Jun 28 |
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Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry. | 2006 Oct 13 |
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Multiwalled carbon nanotubes as sorbent for on-line coupling of solid-phase extraction to high-performance liquid chromatography for simultaneous determination of 10 sulfonamides in eggs and pork. | 2006 Sep 15 |
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Determination of sulfonamides in selected Malaysian swine wastewater by high-performance liquid chromatography. | 2006 Sep 15 |
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In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species. | 2007 |
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Monoclonal antibody-based fluorescence polarization immunoassay for sulfamethoxypyridazine and sulfachloropyridazine. | 2007 Aug 22 |
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Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat. | 2007 Aug 3 |
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An in vivo evaluation of the induction of abnormal sperm morphology by sulphamethoxypyridazine: pyrimethamine (Metakelfin). | 2007 Jan 1 |
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Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection. | 2007 Jan-Feb |
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Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples. | 2007 Mar 21 |
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Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms. | 2007 Mar 28 |
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[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography]. | 2007 Sep |
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Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan. | 2008 Aug |
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Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles. | 2008 Feb 13 |
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Therapeutic effect of a novel oxazolidinone, DA-7867, in BALB/c mice infected with Nocardia brasiliensis. | 2008 Sep 10 |
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Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking. | 2008 Sep 26 |
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Degradation and elimination of various sulfonamides during anaerobic fermentation: a promising step on the way to sustainable pharmacy? | 2009 Apr 1 |
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Determination of ten sulphonamides in egg by liquid chromatography-tandem mass spectrometry. | 2009 Apr 1 |
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A confirmatory method for the simultaneous extraction, separation, identification and quantification of Tetracycline, Sulphonamide, Trimethoprim and Dapsone residues in muscle by ultra-high-performance liquid chromatography-tandem mass spectrometry according to Commission Decision 2002/657/EC. | 2009 Nov 13 |
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Assessment of antimicrobial usage and residues in commercial chicken eggs from smallholder poultry keepers in Morogoro municipality, Tanzania. | 2010 Aug |
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Antibiotic immunosensing: determination of sulfathiazole in water and honey. | 2010 Jun 15 |
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Development and validation of a pressurised liquid extraction liquid chromatography-electrospray-tandem mass spectrometry method for beta-lactams and sulfonamides in animal feed. | 2010 Jun 25 |
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Advantages of soybean peroxidase over horseradish peroxidase as the enzyme label in chemiluminescent enzyme-linked immunosorbent assay of sulfamethoxypyridazine. | 2010 Mar 24 |
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[Enzyme immunoassay for determination of sulfamethoxypyridazine in honey]. | 2010 Mar-Apr |
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Multiresidue analysis of sulfonamides in meat by supramolecular solvent microextraction, liquid chromatography and fluorescence detection and method validation according to the 2002/657/EC decision. | 2010 Oct 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/5939973
Single weekly dose
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/5305584
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29739
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WHO-VATC |
QJ01EW15
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WHO-ATC |
J01ED05
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WHO-VATC |
QJ01EQ15
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757875
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SULFAMETHOXYPYRIDAZINE
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102516
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SULFAMETHOXYPYRIDAZINE
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PRIMARY | Description: A white or yellowish white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; sparingly soluble in ethanol (~750 g/l) TS; soluble in acetone R. Category: Antibacterial. Storage: Sulfamethoxypyridazine should be kept in a well-closed container, protected from light. Additional information: Sulfamethoxypyridazine becomes gradually coloured on exposure to light. Definition: Sulfamethoxypyridazine contains not less than 99.0% and not more than 101.0% of C11H12N4O3S, calculated with reference to the dried substance. | ||
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201-272-5
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80-35-3
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780
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CHEMBL268869
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D013421
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m10321
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C80795
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2515
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100000083251
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5330
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T034E4NS2Z
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10181
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SUB10712MIG
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DB13773
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DTXSID5023611
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)