Sulfapyridine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H11N3O2S
Molecular Weight	249.289
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC=N2

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)

HIDE SMILES / InChI

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

Description
Sources: https://www.drugs.com/cons/sulfapyridine.html | https://www.ncbi.nlm.nih.gov/pubmed/1380664

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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://books.google.ru/books?id=fCysCQAAQBAJ&pg=PA240&lpg=PA240&dq=SULFAPYRIDINE+dihydropteroate+synthase&source=bl&ots=Ue1iKFMUaK&sig=FVvKFniYrHAI_NgNbUNknDitPhI&hl=ru&sa=X&ved=0ahUKEwjnlqjAo7nUAhVLKlAKHTcgCn84ChDoAQg0MAM#v=onepage&q=SULFAPYRIDINE%20dihydropteroate%20synthase&f=false	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatitis herpetiformis 9 Sources: https://www.drugs.com/cons/sulfapyridine.html	Curative		Approved 8583	SULFAPYRIDINE Approved Use Unknown Launch Date 1939

Doses

Dose	Population	Adverse events
75 g multiple, oral Dose: 75 g Route: oral Route: multiple Dose: 75 g Sources: https://pubmed.ncbi.nlm.nih.gov/30436280	unhealthy, 32 years Health Status: unhealthy Age Group: 32 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/30436280	Other AEs: Agranulocytosis... Other AEs: Agranulocytosis (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/30436280
30 g multiple, oral Dose: 30 g Route: oral Route: multiple Dose: 30 g Sources: https://pubmed.ncbi.nlm.nih.gov/21017364	unhealthy, 52 years Health Status: unhealthy Age Group: 52 years Sources: https://pubmed.ncbi.nlm.nih.gov/21017364	Other AEs: Purpura... Other AEs: Purpura (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/21017364
11 g multiple, oral Dose: 11 g Route: oral Route: multiple Dose: 11 g Sources: https://pubmed.ncbi.nlm.nih.gov/20322240	unhealthy, 72 years Health Status: unhealthy Age Group: 72 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20322240	Disc. AE: Anuria... AEs leading to discontinuation/dose reduction: Anuria (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20322240
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8759268	unhealthy, 74.5 years (range: 53 - 86 years) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8759268	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: https://pubmed.ncbi.nlm.nih.gov/8759268
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: https://pubmed.ncbi.nlm.nih.gov/14841400	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14841400	Sources: https://pubmed.ncbi.nlm.nih.gov/14841400

AEs

AE	Significance	Dose	Population
Agranulocytosis	grade 5, 1 patient	75 g multiple, oral Dose: 75 g Route: oral Route: multiple Dose: 75 g Sources: https://pubmed.ncbi.nlm.nih.gov/30436280	unhealthy, 32 years Health Status: unhealthy Age Group: 32 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/30436280
Purpura	grade 5, 1 patient	30 g multiple, oral Dose: 30 g Route: oral Route: multiple Dose: 30 g Sources: https://pubmed.ncbi.nlm.nih.gov/21017364	unhealthy, 52 years Health Status: unhealthy Age Group: 52 years Sources: https://pubmed.ncbi.nlm.nih.gov/21017364
Anuria	grade 5, 1 patient Disc. AE	11 g multiple, oral Dose: 11 g Route: oral Route: multiple Dose: 11 g Sources: https://pubmed.ncbi.nlm.nih.gov/20322240	unhealthy, 72 years Health Status: unhealthy Age Group: 72 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20322240
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: https://pubmed.ncbi.nlm.nih.gov/8759268	unhealthy, 74.5 years (range: 53 - 86 years) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8759268
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: https://pubmed.ncbi.nlm.nih.gov/8759268	unhealthy, 74.5 years (range: 53 - 86 years) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8759268
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: https://pubmed.ncbi.nlm.nih.gov/8759268	unhealthy, 74.5 years (range: 53 - 86 years) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8759268
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: https://pubmed.ncbi.nlm.nih.gov/8759268	unhealthy, 74.5 years (range: 53 - 86 years) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8759268
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: https://pubmed.ncbi.nlm.nih.gov/8759268	unhealthy, 74.5 years (range: 53 - 86 years) Health Status: unhealthy Age Group: 74.5 years (range: 53 - 86 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8759268

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10725317/	likely

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:132842	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132842
ChemicalBook	CB8423160	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8423160
eMolecules	511929	https://www.emolecules.com/cgi-bin/more?vid=511929
MolPort	MolPort-000-883-306	https://www.molport.com/shop/molecule-link/MolPort-000-883-306
Selleck Chemicals	Sulfapyridine(Dagenan)	http://www.selleckchem.com/products/Sulfapyridine(Dagenan).html
ZINC	ZINC000000002105	http://zinc15.docking.org/substances/ZINC000000002105

PubMed

Title	Date	PubMed
The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata.	2008-08-25	18538376
Pharmaceutical and personal care products in tile drainage following land application of municipal biosolids.	2008-07-25	18455753
Pharmacogenetic characterization of sulfasalazine disposition based on NAT2 and ABCG2 (BCRP) gene polymorphisms in humans.	2008-07	18167504
Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography-quadrupole linear ion trap-mass spectrometry.	2008-06-06	18440009
A reliable high-performance liquid chromatography with ultraviolet detection for the determination of sulfonamides in honey.	2008-04-14	18374709
Hepatotoxicity associated with sulfasalazine in inflammatory arthritis: A case series from a local surveillance of serious adverse events.	2008-04-11	18405372
Application of matrix solid-phase dispersion and high-performance liquid chromatography for determination of sulfonamides in honey.	2008-04-02	18376605
A critical analysis of disease-associated DNA polymorphisms in the genes of cattle, goat, sheep, and pig.	2008-04	18350334
Evaluation of in vivo dissolution behavior and GI transit of griseofulvin, a BCS class II drug.	2008-03-20	18037251
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.	2008-02-13	18177003
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].	2008-02	17976730
Immunosuppressive therapy for ocular mucous membrane pemphigoid strategies and outcomes.	2008-02	17655931
An investigation into the acute and chronic toxicity of eleven pharmaceuticals (and their solvents) found in wastewater effluent on the cnidarian, Hydra attenuata.	2008-01-25	17931692
NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances.	2008-01-01	18350883
Distribution of macrolides, sulfonamides, and trimethoprim in tropical waters: ubiquitous occurrence of veterinary antibiotics in the Mekong Delta.	2007-12-01	18186329
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.	2007-11	17960854
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.	2007-11	17868178
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.	2007-11	17632207
Once-daily MMX mesalamine for the treatment of mild-to-moderate ulcerative colitis.	2007-10	18473016
The role of mesalamine in the treatment of ulcerative colitis.	2007-10	18473013
Bowel associated dermatosis - arthritis syndrome: a case report.	2007-09-05	17803823
[Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography].	2007-09	18161331
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007-08-03	17433345
Evaluation of carbon nanotubes as a solid-phase extraction adsorbent for the extraction of cephalosporins antibiotics, sulfonamides and phenolic compounds from aqueous solution.	2007-06-26	17560389
On the action of 5-amino-salicylic acid and sulfapyridine on M. avium including subspecies paratuberculosis.	2007-06-13	17565369
Polymorph VI of sulfapyridine: interpenetrating two- and three-dimensional hydrogen-bonded nets formed from two tautomeric forms.	2007-06	17551192
Health care in Bosnia and Herzegovina before, during, and after 1992-1995 war: a personal testimony.	2007-05-29	17535419
Laccase-mediated michael addition of 15N-sulfapyridine to a model humic constituent.	2007-05-15	17547183
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007-03-22	17373466
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.	2007-03-21	17300200
Therapy of autoimmune bullous diseases.	2007-03	18360613
N-acetyltransferase 2 slow acetylator genotype associated with adverse effects of sulphasalazine in the treatment of inflammatory bowel disease.	2007-03	17377643
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.	2007-02-03	17113817
Determination of sulfonamide compounds in sewage and river by mixed hemimicelles solid-phase extraction prior to liquid chromatography-spectrophotometry.	2007-01-19	17137586
Inflammatory bowel disease: past, present, and future.	2007-01	17322989
Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods.	2006-10-27	16879830
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.	2006-10-13	16822516
Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water.	2006-10	16991204
Review article: high-dose aminosalicylates to induce and maintain remissions in ulcerative colitis.	2006-10	16961743
Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence.	2006-09	16939423
Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection.	2006-08-18	16750659
The metabolism of mesalamine and its possible use in colonic diverticulitis as an anti-inflammatory agent.	2006-08	16885699
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.	2006-06-28	16786990
The Dapsone hypersensitivity syndrome revisited: a potentially fatal multisystem disorder with prominent hepatopulmonary manifestations.	2006-06-06	16756657
Effects of selected pharmaceutical products on phagocytic activity in Elliptio complanata mussels.	2006-06	16533621
Sulfasalazine reduces bile acid induced apoptosis in human hepatoma cells and perfused rat livers.	2006-05	16322111
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2006-01-03	16385979
Effects of Ginkgo biloba extract on inflammatory mediators (SOD, MDA, TNF-alpha, NF-kappaBp65, IL-6) in TNBS-induced colitis in rats.	2006	17392580
Anti-inflammatory and immunosuppressive drugs and reproduction.	2006	16712713
[Induction of tolerance in hypersensitivity to mesalazine (5-ASA)].	2005-12	16454598

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:39:42 GMT 2025` Edited by `admin` on `Wed Apr 02 09:39:42 GMT 2025`
Record UNII	Y5V2N1KE8U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFAPYRIDINE MELTING POINT STANDARD

Preferred Name

English

Sulfapyridine

Official Name

English

NSC-41791

Code

English

SULFAPYRIDINE [USP-RS]

Common Name

English

SULFAPYRIDINE [USP MONOGRAPH]

Common Name

English

SULFASALAZINE IMPURITY J [EP IMPURITY]

Common Name

English

N(SUP 1)-2-PYRIDYLSULFANILAMIDE

Systematic Name

English

SULFAPYRIDINE [USP IMPURITY]

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-N-2-PYRIDINYL-

Systematic Name

English

NSC-4753

Code

English

Sulfapyridine [WHO-DD]

Common Name

English

sulfapyridine [INN]

Common Name

English

SULPHAPYRIDINE

Common Name

English

SULFAPYRIDINE [MART.]

Common Name

English

SULFAPYRIDINE [MI]

Common Name

English

SULFAPYRIDINE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01EQ04