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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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	Inhibitor

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatitis herpetiformis	Curative		Approved	SULFAPYRIDINE

Doses

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Dose	Population	Adverse events
75 g multiple, oral	unhealthy, 32 years	Other AEs: Agranulocytosis...
30 g multiple, oral	unhealthy, 52 years	Other AEs: Purpura...
11 g multiple, oral	unhealthy, 72 years	Disc. AE: Anuria...
500 mg 2 times / day multiple, oral	unhealthy, 74.5 years (range: 53 - 86 years)	Disc. AE: Skin rash, Nausea... Other AEs: Headache, Urinary hesitancy...
4 g 1 times / day multiple, oral Highest studied dose	unhealthy, adult

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AEs

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AE	Significance	Dose	Population
Agranulocytosis	grade 5, 1 patient	75 g multiple, oral	unhealthy, 32 years
Purpura	grade 5, 1 patient	30 g multiple, oral	unhealthy, 52 years
Anuria	grade 5, 1 patient Disc. AE	11 g multiple, oral	unhealthy, 72 years
Headache	1 patient	500 mg 2 times / day multiple, oral	unhealthy, 74.5 years (range: 53 - 86 years)
Urinary hesitancy	1 patient	500 mg 2 times / day multiple, oral	unhealthy, 74.5 years (range: 53 - 86 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9	inhibitor	likely

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.	2001	11570976
Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression.	2001 Aug	11529938
Review article: balsalazide therapy in ulcerative colitis.	2001 Oct	11563993
Role of mesalazine in acute and long-term treatment of ulcerative colitis and its complications.	2002	12408503
Bioavailability factors of isoniazid in fast and slow acetylators, healthy volunteers.	2002 Nov-Dec	12669770

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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