Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2C11H10N3O2S.Ca |
| Molecular Weight | 536.64 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=CC=CC=N2.NC3=CC=C(C=C3)S(=O)(=O)[N-]C4=CC=CC=N4
InChI
InChIKey=YXZNOFHFTBDQKU-UHFFFAOYSA-N
InChI=1S/2C11H10N3O2S.Ca/c2*12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11;/h2*1-8H,12H2;/q2*-1;+2
| Molecular Formula | Ca |
| Molecular Weight | 40.078 |
| Charge | 2 |
| 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 |
unhealthy, 32 years |
Other AEs: Agranulocytosis... |
30 g multiple, oral |
unhealthy, 52 years |
Other AEs: Purpura... |
11 g multiple, oral |
unhealthy, 72 years |
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) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F 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 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Agranulocytosis | grade 5, 1 patient | 75 g multiple, oral |
unhealthy, 32 years |
| Purpura | grade 5, 1 patient | 30 g multiple, oral |
unhealthy, 52 years |
| Anuria | grade 5, 1 patient Disc. AE |
11 g multiple, oral |
unhealthy, 72 years |
| 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) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F 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) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F 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) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F 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) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F 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) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata. | 2008-08-25 |
|
| Pharmaceutical and personal care products in tile drainage following land application of municipal biosolids. | 2008-07-25 |
|
| Pharmacogenetic characterization of sulfasalazine disposition based on NAT2 and ABCG2 (BCRP) gene polymorphisms in humans. | 2008-07 |
|
| Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography-quadrupole linear ion trap-mass spectrometry. | 2008-06-06 |
|
| A reliable high-performance liquid chromatography with ultraviolet detection for the determination of sulfonamides in honey. | 2008-04-14 |
|
| Hepatotoxicity associated with sulfasalazine in inflammatory arthritis: A case series from a local surveillance of serious adverse events. | 2008-04-11 |
|
| Application of matrix solid-phase dispersion and high-performance liquid chromatography for determination of sulfonamides in honey. | 2008-04-02 |
|
| A critical analysis of disease-associated DNA polymorphisms in the genes of cattle, goat, sheep, and pig. | 2008-04 |
|
| Evaluation of in vivo dissolution behavior and GI transit of griseofulvin, a BCS class II drug. | 2008-03-20 |
|
| Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles. | 2008-02-13 |
|
| 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]. | 2008-02 |
|
| Immunosuppressive therapy for ocular mucous membrane pemphigoid strategies and outcomes. | 2008-02 |
|
| An investigation into the acute and chronic toxicity of eleven pharmaceuticals (and their solvents) found in wastewater effluent on the cnidarian, Hydra attenuata. | 2008-01-25 |
|
| NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances. | 2008-01-01 |
|
| Distribution of macrolides, sulfonamides, and trimethoprim in tropical waters: ubiquitous occurrence of veterinary antibiotics in the Mekong Delta. | 2007-12-01 |
|
| Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS. | 2007-11 |
|
| Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate. | 2007-11 |
|
| 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. | 2007-11 |
|
| Once-daily MMX mesalamine for the treatment of mild-to-moderate ulcerative colitis. | 2007-10 |
|
| The role of mesalamine in the treatment of ulcerative colitis. | 2007-10 |
|
| Bowel associated dermatosis - arthritis syndrome: a case report. | 2007-09-05 |
|
| [Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography]. | 2007-09 |
|
| Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat. | 2007-08-03 |
|
| Evaluation of carbon nanotubes as a solid-phase extraction adsorbent for the extraction of cephalosporins antibiotics, sulfonamides and phenolic compounds from aqueous solution. | 2007-06-26 |
|
| On the action of 5-amino-salicylic acid and sulfapyridine on M. avium including subspecies paratuberculosis. | 2007-06-13 |
|
| Polymorph VI of sulfapyridine: interpenetrating two- and three-dimensional hydrogen-bonded nets formed from two tautomeric forms. | 2007-06 |
|
| Health care in Bosnia and Herzegovina before, during, and after 1992-1995 war: a personal testimony. | 2007-05-29 |
|
| Laccase-mediated michael addition of 15N-sulfapyridine to a model humic constituent. | 2007-05-15 |
|
| Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection. | 2007-03-22 |
|
| Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples. | 2007-03-21 |
|
| Therapy of autoimmune bullous diseases. | 2007-03 |
|
| N-acetyltransferase 2 slow acetylator genotype associated with adverse effects of sulphasalazine in the treatment of inflammatory bowel disease. | 2007-03 |
|
| 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. | 2007-02-03 |
|
| Determination of sulfonamide compounds in sewage and river by mixed hemimicelles solid-phase extraction prior to liquid chromatography-spectrophotometry. | 2007-01-19 |
|
| Inflammatory bowel disease: past, present, and future. | 2007-01 |
|
| Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods. | 2006-10-27 |
|
| Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry. | 2006-10-13 |
|
| Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water. | 2006-10 |
|
| Review article: high-dose aminosalicylates to induce and maintain remissions in ulcerative colitis. | 2006-10 |
|
| Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. | 2006-09 |
|
| Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection. | 2006-08-18 |
|
| The metabolism of mesalamine and its possible use in colonic diverticulitis as an anti-inflammatory agent. | 2006-08 |
|
| Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays. | 2006-06-28 |
|
| The Dapsone hypersensitivity syndrome revisited: a potentially fatal multisystem disorder with prominent hepatopulmonary manifestations. | 2006-06-06 |
|
| Effects of selected pharmaceutical products on phagocytic activity in Elliptio complanata mussels. | 2006-06 |
|
| Sulfasalazine reduces bile acid induced apoptosis in human hepatoma cells and perfused rat livers. | 2006-05 |
|
| Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2006-01-03 |
|
| Effects of Ginkgo biloba extract on inflammatory mediators (SOD, MDA, TNF-alpha, NF-kappaBp65, IL-6) in TNBS-induced colitis in rats. | 2006 |
|
| Anti-inflammatory and immunosuppressive drugs and reproduction. | 2006 |
|
| [Induction of tolerance in hypersensitivity to mesalazine (5-ASA)]. | 2005-12 |
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
Mon Mar 31 22:46:38 GMT 2025
by
admin
on
Mon Mar 31 22:46:38 GMT 2025
|
| Record UNII |
35HMH7A87O
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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4374-96-3
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92135670
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6101-39-9
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admin on Mon Mar 31 22:46:38 GMT 2025 , Edited by admin on Mon Mar 31 22:46:38 GMT 2025
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NON-SPECIFIC STOICHIOMETRY | |||
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35HMH7A87O
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DTXSID00365545
Created by
admin on Mon Mar 31 22:46:38 GMT 2025 , Edited by admin on Mon Mar 31 22:46:38 GMT 2025
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |