Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H10N3O2S.Na.H2O |
| Molecular Weight | 289.286 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=CC=CC=N2
InChI
InChIKey=XPORHDMICYKIJE-UHFFFAOYSA-N
InChI=1S/C11H10N3O2S.Na.H2O/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11;;/h1-8H,12H2;;1H2/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 |
| Molecular Formula | HO |
| Molecular Weight | 17.0073 |
| Charge | -1 |
| 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 |
|
| Inhibitory effect of mast cell-mediated immediate-type allergic reactions by sulfapyridine. | 2000 May |
|
| Dapsone and sulfapyridine. | 2001 Jan |
|
| Small bowel motility and colonic transit are altered in dogs with moderate renal failure. | 2001 Jul |
|
| Study of the behaviour, digestive efficiency and gut transit times of crib-biting horses. | 2001 May 12 |
|
| Comparative tolerability of therapies for ulcerative colitis. | 2002 |
|
| N-acetyltransferase 2 genotype-related sulfapyridine acetylation and its adverse events. | 2002 Aug |
|
| 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 |
|
| Idiosyncratic NSAID drug induced oxidative stress. | 2002 Nov 10 |
|
| Dissociated ROS production and ceramide generation in sulfasalazine-induced cell death in Raw 264.7 cells. | 2002 Oct |
|
| The effect of sulfasalazine on rheumatoid arthritic synovial tissue chemokine production. | 2002 Oct |
|
| Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC. | 2004 Apr 2 |
|
| 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 |
|
| Effects of pig slurry on the sorption of sulfonamide antibiotics in soil. | 2004 Jul |
|
| Induction of T lymphocyte apoptosis by sulphasalazine in patients with Crohn's disease. | 2004 Nov |
|
| Ronin, PhD. | 2004 Sep |
|
| Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection. | 2004 Sep-Oct |
|
| Microbial inhibition by pharmaceutical antibiotics in different soils--dose-response relations determined with the iron(III) reduction test. | 2005 Apr |
|
| [Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry]. | 2005 Jul |
|
| Potential of nuclear quadrupole resonance in pharmaceutical analysis. | 2005 Jul 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 |
|
| 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 |
|
| Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods. | 2006 Oct 27 |
|
| 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 |
|
| On the action of 5-amino-salicylic acid and sulfapyridine on M. avium including subspecies paratuberculosis. | 2007 Jun 13 |
|
| 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 |
|
| Laccase-mediated michael addition of 15N-sulfapyridine to a model humic constituent. | 2007 May 15 |
|
| 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 |
|
| Removal of selected pharmaceuticals and personal care products (PPCPs) and endocrine-disrupting chemicals (EDCs) during sand filtration and ozonation at a municipal sewage treatment plant. | 2007 Nov |
|
| 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 |
|
| Hepatotoxicity associated with sulfasalazine in inflammatory arthritis: A case series from a local surveillance of serious adverse events. | 2008 Apr 11 |
|
| 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 |
|
| An investigation into the acute and chronic toxicity of eleven pharmaceuticals (and their solvents) found in wastewater effluent on the cnidarian, Hydra attenuata. | 2008 Jan 25 |
|
| 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
Wed Jul 05 23:01:49 UTC 2023
by
admin
on
Wed Jul 05 23:01:49 UTC 2023
|
| Record UNII |
FV94Y8O7J7
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| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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Systematic Name | English |
| Code System | Code | Type | Description | ||
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23675732
Created by
admin on Wed Jul 05 23:01:50 UTC 2023 , Edited by admin on Wed Jul 05 23:01:50 UTC 2023
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PRIMARY | |||
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FV94Y8O7J7
Created by
admin on Wed Jul 05 23:01:50 UTC 2023 , Edited by admin on Wed Jul 05 23:01:50 UTC 2023
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PRIMARY | |||
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6101-41-3
Created by
admin on Wed Jul 05 23:01:50 UTC 2023 , Edited by admin on Wed Jul 05 23:01:50 UTC 2023
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |