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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
Structure of SULFAPYRIDINE SODIUM MONOHYDRATE

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;

HIDE SMILES / InChI

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.

Approval Year

Doses

Doses

DosePopulationAdverse events​
75 g multiple, oral (total)
Dose: 75 g
Route: oral
Route: multiple
Dose: 75 g
Sources:
unhealthy, 32 years
n = 1
Health Status: unhealthy
Age Group: 32 years
Sex: F
Population Size: 1
Sources:
Other AEs: Agranulocytosis...
Other AEs:
Agranulocytosis (grade 5, 1 patient)
Sources:
30 g multiple, oral (total)
Dose: 30 g
Route: oral
Route: multiple
Dose: 30 g
Sources:
unhealthy, 52 years
n = 1
Health Status: unhealthy
Condition: pneumonia
Age Group: 52 years
Population Size: 1
Sources:
Other AEs: Purpura...
Other AEs:
Purpura (grade 5, 1 patient)
Sources:
11 g multiple, oral (total)
Dose: 11 g
Route: oral
Route: multiple
Dose: 11 g
Sources:
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)
Nausea (2 patients)
Other AEs:
Headache (1 patient)
Urinary hesitancy (1 patient)
Lymphopenia (grade 1, 1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
Agranulocytosis grade 5, 1 patient
75 g multiple, oral (total)
Dose: 75 g
Route: oral
Route: multiple
Dose: 75 g
Sources:
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)
Dose: 30 g
Route: oral
Route: multiple
Dose: 30 g
Sources:
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)
Dose: 11 g
Route: oral
Route: multiple
Dose: 11 g
Sources:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
PubMed

PubMed

TitleDatePubMed
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

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 Fri Dec 16 17:22:08 UTC 2022
Edited
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
SULFAPYRIDINE SODIUM MONOHYDRATE
Common Name English
SODIUM SULFAPYRIDINE MONOHYDRATE
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-PYRIDINYL-, SODIUM SALT, HYDRATE (1:1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
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
PRIMARY
FDA UNII
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
PRIMARY
CAS
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
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY