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 | HO |
| Molecular Weight | 17.0073 |
| 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 |
|
| Inhibitory effect of mast cell-mediated immediate-type allergic reactions by sulfapyridine. | 2000 May |
|
| Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis. | 2001 |
|
| Dapsone and sulfapyridine. | 2001 Jan |
|
| Review article: balsalazide therapy in ulcerative colitis. | 2001 Oct |
|
| Regulation of human B cell function by sulfasalazine and its metabolites. | 2002 Apr |
|
| 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 |
|
| Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey. | 2003 Jun |
|
| Effect of food on gastrointestinal transit of liquids in cynomolgus monkeys. | 2003 May |
|
| Influence of age and body size on orocecal transit time as assessed by use of the sulfasalazine method in healthy dogs. | 2003 Sep |
|
| 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 |
|
| 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 |
|
| Sulfasalazine and dermatitis herpetiformis. | 2005 May |
|
| Anti-inflammatory and immunosuppressive drugs and reproduction. | 2006 |
|
| 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 |
|
| Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays. | 2006 Jun 28 |
|
| The Dapsone hypersensitivity syndrome revisited: a potentially fatal multisystem disorder with prominent hepatopulmonary manifestations. | 2006 Jun 6 |
|
| 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 |
|
| Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods. | 2006 Oct 27 |
|
| Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. | 2006 Sep |
|
| Distribution of macrolides, sulfonamides, and trimethoprim in tropical waters: ubiquitous occurrence of veterinary antibiotics in the Mekong Delta. | 2007 Dec 1 |
|
| Report of the IWGT working group on strategy/interpretation for regulatory in vivo tests II. Identification of in vivo-only positive compounds in the bone marrow micronucleus test. | 2007 Feb 3 |
|
| Determination of sulfonamide compounds in sewage and river by mixed hemimicelles solid-phase extraction prior to liquid chromatography-spectrophotometry. | 2007 Jan 19 |
|
| 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 |
|
| Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS. | 2007 Nov |
|
| Once-daily MMX mesalamine for the treatment of mild-to-moderate 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 critical analysis of disease-associated DNA polymorphisms in the genes of cattle, goat, sheep, and pig. | 2008 Apr |
|
| 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 |
|
| New Ni(II)-sulfonamide complexes: synthesis, structural characterization and antibacterial properties. X-ray diffraction of [Ni(sulfisoxazole)2(H2O)4].2H2O and [Ni(sulfapyridine)2]. | 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 |
|
| Pharmacogenetic characterization of sulfasalazine disposition based on NAT2 and ABCG2 (BCRP) gene polymorphisms in humans. | 2008 Jul |
|
| 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 |
|
| Evaluation of in vivo dissolution behavior and GI transit of griseofulvin, a BCS class II drug. | 2008 Mar 20 |
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 17:22:08 UTC 2022
by
admin
on
Fri Dec 16 17:22:08 UTC 2022
|
| Record UNII |
FV94Y8O7J7
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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| Name | Type | Language | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
| Code System | Code | Type | Description | ||
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23675732
Created by
admin on Fri Dec 16 17:22:08 UTC 2022 , Edited by admin on Fri Dec 16 17:22:08 UTC 2022
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PRIMARY | |||
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FV94Y8O7J7
Created by
admin on Fri Dec 16 17:22:08 UTC 2022 , Edited by admin on Fri Dec 16 17:22:08 UTC 2022
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PRIMARY | |||
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6101-41-3
Created by
admin on Fri Dec 16 17:22:08 UTC 2022 , Edited by admin on Fri Dec 16 17:22:08 UTC 2022
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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 |