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 (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 |
|---|---|---|
| Dapsone and sulfapyridine. | 2001 Jan |
|
| Simple and simultaneous determination of sulphapyridine and acetylsulphapyridine in human serum by column-switching high-performance liquid chromatography. | 2002 Dec |
|
| Successful treatment of postoperative pyoderma gangrenosum with cyclosporin. | 2002 Mar |
|
| [Pharmacokinetics of salazosulfapyridine in a hemodialysis patient]. | 2003 Jun |
|
| Sulphasalazine-induced leucopenia in a patient with renal dysfunction. | 2003 Jun |
|
| 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 |
|
| 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 |
|
| Occurrence of antimicrobials in the final effluents of wastewater treatment plants in Canada. | 2004 Jul 1 |
|
| Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection. | 2004 Sep-Oct |
|
| [Induction of tolerance in hypersensitivity to mesalazine (5-ASA)]. | 2005 Dec |
|
| Occurrence and sorption behavior of sulfonamides, macrolides, and trimethoprim in activated sludge treatment. | 2005 Jun 1 |
|
| Novel sulfasalazine analogues with enhanced NF-kB inhibitory and apoptosis promoting activity. | 2005 May |
|
| [Drug therapy for ulcerative colitis: salazosulfapyridine and 5-ASA]. | 2005 May |
|
| Sulfasalazine and dermatitis herpetiformis. | 2005 May |
|
| The metabolism of mesalamine and its possible use in colonic diverticulitis as an anti-inflammatory agent. | 2006 Aug |
|
| Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. | 2006 Sep |
|
| 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 |
|
| Therapy of autoimmune bullous diseases. | 2007 Mar |
|
| 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 |
|
| [Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography]. | 2007 Sep |
|
| The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata. | 2008 Aug 25 |
|
| Pharmaceutical and personal care products in tile drainage following land application of municipal biosolids. | 2008 Jul 25 |
|
| 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
Sat Dec 16 09:40:06 UTC 2023
by
admin
on
Sat Dec 16 09:40:06 UTC 2023
|
| Record UNII |
35HMH7A87O
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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4374-96-3
Created by
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92135670
Created by
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6101-39-9
Created by
admin on Sat Dec 16 09:40:06 UTC 2023 , Edited by admin on Sat Dec 16 09:40:06 UTC 2023
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NON-SPECIFIC STOICHIOMETRY | |||
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35HMH7A87O
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DTXSID00365545
Created by
admin on Sat Dec 16 09:40:06 UTC 2023 , Edited by admin on Sat Dec 16 09:40:06 UTC 2023
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |