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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11N3O2S
Molecular Weight 249.2904
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAPYRIDINE

SMILES

c1ccnc(c1)NS(=O)(=O)c2ccc(cc2)N

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 249.2904
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
Comparative absorption of 5-aminosalicylic acid (5-ASA) after administration of a 5-ASA enema and salazosulfapyridine (SASP) after an SASP suppository in Japanese volunteers.
2002 Feb
The effect of sulfasalazine on rheumatoid arthritic synovial tissue chemokine production.
2002 Oct
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
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
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
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.
2004 Jul-Aug
Susceptibility of Desulfovibrio desulfuricans intestinal strains to sulfasalazine and its biotransformation products.
2004 Jun
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
Effects of sulfonamide and tetracycline antibiotics on soil microbial activity and microbial biomass.
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
Potential of nuclear quadrupole resonance in pharmaceutical analysis.
2005 Jul 1
[Drug therapy for ulcerative colitis: salazosulfapyridine and 5-ASA].
2005 May
Sulfasalazine and dermatitis herpetiformis.
2005 May
Free radical scavenging reactions of sulfasalazine, 5-aminosalicylic acid and sulfapyridine: mechanistic aspects and antioxidant activity.
2005 Nov
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
Effects of Ginkgo biloba extract on inflammatory mediators (SOD, MDA, TNF-alpha, NF-kappaBp65, IL-6) in TNBS-induced colitis in rats.
2006
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
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
Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water.
2006 Oct
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
Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence.
2006 Sep
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
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
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
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
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
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
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 Jun 25 20:53:56 UTC 2021
Edited
by admin
on Fri Jun 25 20:53:56 UTC 2021
Record UNII
Y5V2N1KE8U
Record Status Validated (UNII)
Record Version
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Name Type Language
SULFAPYRIDINE
INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
NSC-41791
Code English
SULFAPYRIDINE [USP-RS]
Common Name English
SULFAPYRIDINE [USP MONOGRAPH]
Common Name English
N(SUP 1)-2-PYRIDYLSULFANILAMIDE
Systematic 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 MELTING POINT STANDARD
USP-RS  
Common Name English
SULFAPYRIDINE [MART.]
Common Name English
SULFASALAZINE SPECIFIED IMPURITY J [EP]
Common Name English
SULFAPYRIDINE [USP]
Common Name English
SULFAPYRIDINE [MI]
Common Name English
SULFAPYRIDINE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01EQ04
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
NCI_THESAURUS C29739
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
FDA ORPHAN DRUG 51090
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
WHO-ATC J01EB04
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
Code System Code Type Description
EVMPD
SUB10724MIG
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
WIKIPEDIA
Sulfapyridine
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
USP_CATALOG
1634000
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
205-642-7
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
DRUG CENTRAL
2524
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL700
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
DRUG BANK
DB00891
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
FDA UNII
Y5V2N1KE8U
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
EPA CompTox
144-83-2
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
NCI_THESAURUS
C66570
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
RXCUI
10188
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY RxNorm
PUBCHEM
5336
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
INN
4165
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PRIMARY
CAS
144-83-2
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
MESH
D013427
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY
MERCK INDEX
M10339
Created by admin on Fri Jun 25 20:53:56 UTC 2021 , Edited by admin on Fri Jun 25 20:53:56 UTC 2021
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE INACTIVE
Not inhibite the Hb-catalyzed peroxidative reaction
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY