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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 C11H11N3O2S
Molecular Weight 249.289
Charge 0
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

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
Dapsone and sulfapyridine.
2001 Jan
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
Comparative tolerability of therapies for ulcerative colitis.
2002
N-acetyltransferase 2 genotype-related sulfapyridine acetylation and its adverse events.
2002 Aug
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
Idiosyncratic NSAID drug induced oxidative stress.
2002 Nov 10
Dissociated ROS production and ceramide generation in sulfasalazine-induced cell death in Raw 264.7 cells.
2002 Oct
The effect of sulfasalazine on rheumatoid arthritic synovial tissue chemokine production.
2002 Oct
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
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.
2004 Jul
Induction of T lymphocyte apoptosis by sulphasalazine in patients with Crohn's disease.
2004 Nov
Ronin, PhD.
2004 Sep
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
[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
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
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
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
Distribution of macrolides, sulfonamides, and trimethoprim in tropical waters: ubiquitous occurrence of veterinary antibiotics in the Mekong Delta.
2007 Dec 1
Inflammatory bowel disease: past, present, and future.
2007 Jan
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
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
Therapy of autoimmune bullous diseases.
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
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.
2007 Nov
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 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
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
The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata.
2008 Aug 25
Immunosuppressive therapy for ocular mucous membrane pemphigoid strategies and outcomes.
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
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
Application of matrix solid-phase dispersion and high-performance liquid chromatography for determination of sulfonamides in honey.
2008 Jan-Feb
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
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 Wed Jul 05 23:01:49 UTC 2023
Edited
by admin
on Wed Jul 05 23:01:49 UTC 2023
Record UNII
FV94Y8O7J7
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 23:01:50 UTC 2023 , Edited by admin on Wed Jul 05 23:01:50 UTC 2023
PRIMARY
FDA UNII
FV94Y8O7J7
Created by admin on Wed Jul 05 23:01:50 UTC 2023 , Edited by admin on Wed Jul 05 23:01:50 UTC 2023
PRIMARY
CAS
6101-41-3
Created by admin on Wed Jul 05 23:01:50 UTC 2023 , Edited by admin on Wed Jul 05 23:01:50 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY