Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H11N3O2S |
| Molecular Weight | 249.2904 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccnc(c1)NS(=O)(=O)c2ccc(cc2)N
InChI
InChIKey=GECHUMIMRBOMGK-UHFFFAOYSA-N
InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
| Molecular Formula | C11H11N3O2S |
| Molecular Weight | 249.2904 |
| 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 |
|---|---|---|
| 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 |
|
| The effect of sulfasalazine on rheumatoid arthritic synovial tissue chemokine production. | 2002 Oct |
|
| Effect of food on gastrointestinal transit of liquids in cynomolgus monkeys. | 2003 May |
|
| 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 |
|
| N-acetyltransferase 2 genotype-related efficacy of sulfasalazine in patients with rheumatoid arthritis. | 2004 Feb |
|
| General principles of pharmaceutical solid polymorphism: a supramolecular perspective. | 2004 Feb 23 |
|
| Effects of pig slurry on the sorption of sulfonamide antibiotics in soil. | 2004 Jul |
|
| 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 |
|
| 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 |
|
| Effects of sulfonamide and tetracycline antibiotics on soil microbial activity and microbial biomass. | 2005 Apr |
|
| [Induction of tolerance in hypersensitivity to mesalazine (5-ASA)]. | 2005 Dec |
|
| [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 |
|
| [Drug therapy for ulcerative colitis: salazosulfapyridine and 5-ASA]. | 2005 May |
|
| Sulfasalazine and dermatitis herpetiformis. | 2005 May |
|
| Free radical scavenging reactions of sulfasalazine, 5-aminosalicylic acid and sulfapyridine: mechanistic aspects and antioxidant activity. | 2005 Nov |
|
| Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry. | 2005 Sep-Oct |
|
| 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 |
|
| 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 |
|
| Effects of selected pharmaceutical products on phagocytic activity in Elliptio complanata mussels. | 2006 Jun |
|
| 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 |
|
| 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 |
|
| Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. | 2006 Sep |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 Jun 25 20:53:56 UTC 2021
by
admin
on
Fri Jun 25 20:53:56 UTC 2021
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| Record UNII |
Y5V2N1KE8U
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-VATC |
QJ01EQ04
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NCI_THESAURUS |
C29739
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FDA ORPHAN DRUG |
51090
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WHO-ATC |
J01EB04
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| Code System | Code | Type | Description | ||
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SUB10724MIG
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Sulfapyridine
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1634000
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205-642-7
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2524
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CHEMBL700
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DB00891
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144-83-2
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C66570
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5336
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4165
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144-83-2
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D013427
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M10339
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> METABOLITE INACTIVE |
Not inhibite the Hb-catalyzed peroxidative reaction
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
