Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H10N3O2S.Na |
| Molecular Weight | 271.271 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=CC=CC=N2
InChI
InChIKey=DAINBAXHBFSNCQ-UHFFFAOYSA-N
InChI=1S/C11H10N3O2S.Na/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11;/h1-8H,12H2;/q-1;+1
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C11H11N3O2S |
| Molecular Weight | 249.289 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. It was used to treat of infections in humans in particular, dermatitis herpetiformis (Duhring's disease), a skin problem, but that usage was discontinued by manufacturer. It is also known, that sulfapyridine is one of the two primary metabolite of the anti-inflammatory drug salicylazosulfapyridine.
Originator
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
75 g multiple, oral (total) |
unhealthy, 32 years n = 1 Health Status: unhealthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
Other AEs: Agranulocytosis... |
30 g multiple, oral (total) |
unhealthy, 52 years n = 1 Health Status: unhealthy Condition: pneumonia Age Group: 52 years Population Size: 1 Sources: |
Other AEs: Purpura... |
11 g multiple, oral (total) |
unhealthy, 72 years n = 1 Health Status: unhealthy Age Group: 72 years Sex: F Population Size: 1 Sources: |
Disc. AE: Anuria... AEs leading to discontinuation/dose reduction: Anuria (grade 5, 1 patient) Sources: |
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 74.5 years (range: 53 - 86 years) n = 20 Health Status: unhealthy Condition: ocular inflammation Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Population Size: 20 Sources: |
Disc. AE: Skin rash, Nausea... Other AEs: Headache, Urinary hesitancy... AEs leading to discontinuation/dose reduction: Skin rash (3 patients) Other AEs:Nausea (2 patients) Headache (1 patient) Sources: Urinary hesitancy (1 patient) Lymphopenia (grade 1, 1 patient) |
4 g 1 times / day multiple, oral Highest studied dose Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: eczema-dermatiti Age Group: adult Sex: M+F Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Agranulocytosis | grade 5, 1 patient | 75 g multiple, oral (total) |
unhealthy, 32 years n = 1 Health Status: unhealthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
| Purpura | grade 5, 1 patient | 30 g multiple, oral (total) |
unhealthy, 52 years n = 1 Health Status: unhealthy Condition: pneumonia Age Group: 52 years Population Size: 1 Sources: |
| Anuria | grade 5, 1 patient Disc. AE |
11 g multiple, oral (total) |
unhealthy, 72 years n = 1 Health Status: unhealthy Age Group: 72 years Sex: F Population Size: 1 Sources: |
| Headache | 1 patient | 500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 74.5 years (range: 53 - 86 years) n = 20 Health Status: unhealthy Condition: ocular inflammation Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Population Size: 20 Sources: |
| Urinary hesitancy | 1 patient | 500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 74.5 years (range: 53 - 86 years) n = 20 Health Status: unhealthy Condition: ocular inflammation Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Population Size: 20 Sources: |
| Nausea | 2 patients Disc. AE |
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 74.5 years (range: 53 - 86 years) n = 20 Health Status: unhealthy Condition: ocular inflammation Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Population Size: 20 Sources: |
| Skin rash | 3 patients Disc. AE |
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 74.5 years (range: 53 - 86 years) n = 20 Health Status: unhealthy Condition: ocular inflammation Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Population Size: 20 Sources: |
| Lymphopenia | grade 1, 1 patient | 500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 74.5 years (range: 53 - 86 years) n = 20 Health Status: unhealthy Condition: ocular inflammation Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Population Size: 20 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of sulfasalazine and its metabolites on steady state messenger RNA concentrations for inflammatory cytokines, matrix metalloproteinases, and tissue inhibitors of metalloproteinase in rheumatoid synovial fibroblasts. | 2000 Mar |
|
| Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis. | 2001 |
|
| Dapsone and sulfapyridine. | 2001 Jan |
|
| Kinetic phenotypic diagnosis of N-acetylation polymorphism in patients based on ratio of urinary metabolites of salicylazosulfapyridine. | 2001 Oct 23 |
|
| Comparative tolerability of therapies for ulcerative colitis. | 2002 |
|
| Regulation of human B cell function by sulfasalazine and its metabolites. | 2002 Apr |
|
| N-acetyltransferase 2 genotype-related sulfapyridine acetylation and its adverse events. | 2002 Aug |
|
| Simple and simultaneous determination of sulphapyridine and acetylsulphapyridine in human serum by column-switching high-performance liquid chromatography. | 2002 Dec |
|
| Comparative absorption of 5-aminosalicylic acid (5-ASA) after administration of a 5-ASA enema and salazosulfapyridine (SASP) after an SASP suppository in Japanese volunteers. | 2002 Feb |
|
| N-acetyltransferase 1 and 2 genotypes do not predict response or toxicity to treatment with mesalamine and sulfasalazine in patients with ulcerative colitis. | 2002 Jul |
|
| Successful treatment of postoperative pyoderma gangrenosum with cyclosporin. | 2002 Mar |
|
| Bioavailability factors of isoniazid in fast and slow acetylators, healthy volunteers. | 2002 Nov-Dec |
|
| The effect of sulfasalazine on rheumatoid arthritic synovial tissue chemokine production. | 2002 Oct |
|
| Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey. | 2003 Jun |
|
| Effects of pig slurry on the sorption of sulfonamide antibiotics in soil. | 2004 Jul |
|
| Occurrence of antimicrobials in the final effluents of wastewater treatment plants in Canada. | 2004 Jul 1 |
|
| Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions. | 2004 Jul-Aug |
|
| Susceptibility of Desulfovibrio desulfuricans intestinal strains to sulfasalazine and its biotransformation products. | 2004 Jun |
|
| Effects of sulfonamide and tetracycline antibiotics on soil microbial activity and microbial biomass. | 2005 Apr |
|
| [Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
|
| Occurrence and sorption behavior of sulfonamides, macrolides, and trimethoprim in activated sludge treatment. | 2005 Jun 1 |
|
| Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2005 Sep-Oct |
|
| The metabolism of mesalamine and its possible use in colonic diverticulitis as an anti-inflammatory agent. | 2006 Aug |
|
| 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 |
|
| The Dapsone hypersensitivity syndrome revisited: a potentially fatal multisystem disorder with prominent hepatopulmonary manifestations. | 2006 Jun 6 |
|
| Sulfasalazine reduces bile acid induced apoptosis in human hepatoma cells and perfused rat livers. | 2006 May |
|
| Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water. | 2006 Oct |
|
| Review article: high-dose aminosalicylates to induce and maintain remissions in ulcerative colitis. | 2006 Oct |
|
| Distribution of macrolides, sulfonamides, and trimethoprim in tropical waters: ubiquitous occurrence of veterinary antibiotics in the Mekong Delta. | 2007 Dec 1 |
|
| Inflammatory bowel disease: past, present, and future. | 2007 Jan |
|
| 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 |
|
| Evaluation of carbon nanotubes as a solid-phase extraction adsorbent for the extraction of cephalosporins antibiotics, sulfonamides and phenolic compounds from aqueous solution. | 2007 Jun 26 |
|
| Therapy of autoimmune bullous diseases. | 2007 Mar |
|
| N-acetyltransferase 2 slow acetylator genotype associated with adverse effects of sulphasalazine in the treatment of inflammatory bowel disease. | 2007 Mar |
|
| Laccase-mediated michael addition of 15N-sulfapyridine to a model humic constituent. | 2007 May 15 |
|
| Health care in Bosnia and Herzegovina before, during, and after 1992-1995 war: a personal testimony. | 2007 May 29 |
|
| Once-daily MMX mesalamine for the treatment of mild-to-moderate ulcerative colitis. | 2007 Oct |
|
| The role of mesalamine in the treatment of ulcerative colitis. | 2007 Oct |
|
| [Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography]. | 2007 Sep |
|
| Bowel associated dermatosis - arthritis syndrome: a case report. | 2007 Sep 5 |
|
| A reliable high-performance liquid chromatography with ultraviolet detection for the determination of sulfonamides in honey. | 2008 Apr 14 |
|
| The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata. | 2008 Aug 25 |
|
| Immunosuppressive therapy for ocular mucous membrane pemphigoid strategies and outcomes. | 2008 Feb |
|
| Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles. | 2008 Feb 13 |
|
| NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances. | 2008 Jan 1 |
|
| Application of matrix solid-phase dispersion and high-performance liquid chromatography for determination of sulfonamides in honey. | 2008 Jan-Feb |
|
| Pharmaceutical and personal care products in tile drainage following land application of municipal biosolids. | 2008 Jul 25 |
|
| Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography-quadrupole linear ion trap-mass spectrometry. | 2008 Jun 6 |
Patents
Sample Use Guides
For dermatitis herpetiformis: adults and adolescents: 250 milligrams to 1 gram four times a day until improvement occurs. After improvement has occurred, the dose should then be reduced by 250 to 500 milligrams every three days until there are no symptoms; that dose should be taken once daily. Children: use is not recommended, because children usually do not get this condition.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Sulfapyridine (SP) and 5-aminosalicylic acid (5-ASA) are the two primary metabolites of the anti-inflammatory drug salicylazosulfapyridine (SASP). These two metabolites were studied for induction of chromosomal damage in mammalian cells, in vitro and in vivo, in an attempt to understand better the genetic effects produced by SASP in humans and laboratory mice. To this end, SP and 5-ASA were tested for induction of sister-chromatid exchanges (SCE) and chromosomal aberrations (Abs) in Chinese hamster ovary (CHO) cells in vitro. SP gave positive results in the in vitro SCE test and negative results in the in vitro Abs test.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:13:48 UTC 2022
by
admin
on
Fri Dec 16 16:13:48 UTC 2022
|
| Record UNII |
H3SKB3662O
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29739
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| Code System | Code | Type | Description | ||
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127-57-1
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H3SKB3662O
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CHEMBL700
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204-850-5
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C73842
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M10339
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PRIMARY | Merck Index | ||
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DTXSID6059570
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23667654
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| Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |