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
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 |
|
| Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression. | 2001 Aug |
|
| Maturation of human dendritic cells as sulfasalazine target. | 2001 Aug |
|
| 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 |
|
| Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug. | 2001 Oct |
|
| Review article: balsalazide therapy in ulcerative colitis. | 2001 Oct |
|
| Regulation of human B cell function by sulfasalazine and its metabolites. | 2002 Apr |
|
| Successful treatment of postoperative pyoderma gangrenosum with cyclosporin. | 2002 Mar |
|
| Bioavailability factors of isoniazid in fast and slow acetylators, healthy volunteers. | 2002 Nov-Dec |
|
| [Pharmacokinetics of salazosulfapyridine in a hemodialysis patient]. | 2003 Jun |
|
| Sulphasalazine-induced leucopenia in a patient with renal dysfunction. | 2003 Jun |
|
| Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey. | 2003 Jun |
|
| Evaluation of biotransformation of sulphasalazine in the colon epithelial Caco-2 cells. | 2004 Dec |
|
| 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 |
|
| 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 |
|
| Induction of T lymphocyte apoptosis by sulphasalazine in patients with Crohn's disease. | 2004 Nov |
|
| Microbial inhibition by pharmaceutical antibiotics in different soils--dose-response relations determined with the iron(III) reduction test. | 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 |
|
| Anti-inflammatory and immunosuppressive drugs and reproduction. | 2006 |
|
| 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 |
|
| 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 |
|
| Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. | 2006 Sep |
|
| Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat. | 2007 Aug 3 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata. | 2008 Aug 25 |
|
| Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles. | 2008 Feb 13 |
|
| 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 |
|
| 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
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| Code System | Code | Type | Description | ||
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4374-96-3
Created by
admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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PRIMARY | |||
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92135670
Created by
admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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PRIMARY | |||
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6101-39-9
Created by
admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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NON-SPECIFIC STOICHIOMETRY | |||
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35HMH7A87O
Created by
admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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PRIMARY | |||
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DTXSID00365545
Created by
admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
