Sulfapyridine

Identification

Summary

Sulfapyridine is a sulfonamide antibiotic used to treat dermatitis herpetiformis, benign mucous membrane pemphigoid and pyoderma gangrenosum.

Generic Name
Sulfapyridine
DrugBank Accession Number
DB00891
Background

Antibacterial, potentially toxic, and previously used to treat certain skin diseases. No longer prescribed.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 249.289
Monoisotopic: 249.057197301
Chemical Formula
C11H11N3O2S
Synonyms
  • 2-(p-Aminobenzenesulphonamido)pyridine
  • 2-Sulfanilamidopyridin
  • 2-Sulfanilamidopyridine
  • 2-Sulfanilylaminopyridine
  • 2-Sulfapyridine
  • 4-(2-Pyridinylsulfonyl)aniline
  • 4-[(2-Pyridylamino)sulfonyl]aniline
  • 4-Amino-N-pyridin-2-yl-benzenesulfonamide
  • 4-Amino-N,2-pyridinylbenzenesulfonamide
  • N-2-Pyridylsulfanilamide
  • N(1)-2-Pyridylsulfanilamide
  • N(1)-Pyridylsulfanilamide
  • Solfapiridina
  • Sulfapiridina
  • Sulfapyridin
  • Sulfapyridine
  • Sulfapyridinum
  • Sulphapyridine
External IDs
  • M & B 693
  • N000159

Pharmacology

Indication

For the treatment of dermatitis herpetiformis, benign mucous membrane pemphigoid and pyoderma gangrenosum

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Pharmacodynamics

Sulfapyridine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.

Mechanism of action

Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid by means of processing the substrate para-aminobenzoic acid (PABA). Dihydropteroate synthetase activity is vital in the synthesis of folate, and folate is required for cells to make nucleic acids, such as DNA or RNA. So if DNA molecules cannot be built, the cell cannot divide.

TargetActionsOrganism
UDihydropteroate synthase type-1
inhibitor
Mycobacterium fortuitum
Absorption

Approximately 60-80%

Volume of distribution

Not Available

Protein binding

Approximately 50% bound to plasma proteins.

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

6-14 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

LD50 is 15800 mg/kg (orally in rats).

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Sulfapyridine.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfapyridine.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Sulfapyridine.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Sulfapyridine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfapyridine.
Food Interactions
Not Available

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dagenan Tab 500mgTablet500 mgOralAventis Pharma Ltd.1992-12-312003-07-22Canada flag

Categories

ATC Codes
G01AE10 — Combinations of sulfonamidesJ01EB04 — Sulfapyridine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Pyridines and derivatives / Organosulfonamides / Imidolactams / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds
show 2 more
Substituents
Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
substituted aniline, sulfonamide, pyridines, sulfonamide antibiotic (CHEBI:132842)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Y5V2N1KE8U
CAS number
144-83-2
InChI Key
GECHUMIMRBOMGK-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-amino-N-(pyridin-2-yl)benzene-1-sulfonamide
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N1

References

General References
Not Available
Human Metabolome Database
HMDB0015028
KEGG Drug
D02434
PubChem Compound
5336
PubChem Substance
46506991
ChemSpider
5145
BindingDB
39340
RxNav
10188
ChEBI
132842
ChEMBL
CHEMBL700
ZINC
ZINC000000002105
Therapeutic Targets Database
DAP001200
PharmGKB
PA164779050
PDBe Ligand
SFY
Wikipedia
Sulfapyridine
PDB Entries
4hwk / 5r9p / 5rf8 / 5rzb / 6mwf / 7b8d
MSDS
Download (72.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Eli lilly and co
Packagers
  • Amend
  • Prime European Therapeuticals SPA
Dosage Forms
FormRouteStrength
TabletOral500 mg
Prices
Unit descriptionCostUnit
Sulfapyridine powder0.13USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)192 °CPhysProp
water solubility268 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.35HANSCH,C ET AL. (1995)
logS-2.7ADME Research, USCD
pKa8.43PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility0.235 mg/mLALOGPS
logP0.84ALOGPS
logP1.01Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)6.24Chemaxon
pKa (Strongest Basic)2.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area85.08 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity65.75 m3·mol-1Chemaxon
Polarizability24.97 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9884
Blood Brain Barrier+0.9552
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.8936
P-glycoprotein inhibitor INon-inhibitor0.9418
P-glycoprotein inhibitor IINon-inhibitor0.9009
Renal organic cation transporterNon-inhibitor0.8822
CYP450 2C9 substrateNon-substrate0.7789
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7808
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9389
CYP450 2C19 inhibitorNon-inhibitor0.953
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7533
Ames testNon AMES toxic0.9347
CarcinogenicityNon-carcinogens0.9209
BiodegradationNot ready biodegradable0.992
Rat acute toxicity1.2293 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.921
hERG inhibition (predictor II)Non-inhibitor0.8512
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.66 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0537-9230000000-93117665cf41b575fe9d
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-0090000000-6205fa17064877bf03df
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a59-4900000000-27a3388f44d41a748f99
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a59-4920000000-ddd28eca3499faaddfb1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-76404b7958aaaddb00c3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0090000000-b794dcd70eedfd04a9e8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-1690000000-d32f010faae95dd6e5dd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-3900000000-b89b3d587bf8893e343a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-7900000000-e9c1ce1a2bfb8587016b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-9600000000-c2b3b96e2d3db5fc940f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05mo-9400000000-6eeb6714b222ec20731e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0090000000-14bd7d3423dbbc1677f5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-1690000000-ec5ad1677ec436c15076
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-3900000000-3221fbcec55c511e58a0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-7900000000-4959721f5e57ee1708c5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-9600000000-cb7f712bbbba5e75ed73
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05mo-9400000000-542a7f83b7c124aeaa3b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-0900000000-ebce9cc4e8380518ddec
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-5900000000-c36697c8e5b4522ccfc5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-9600000000-07faf61cc06e82c703a6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-2ae47a77fd32fcf2200e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-0900000000-4653688bc5b5c91f5a27
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-2790000000-4dc2c83a110029089a1c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a59-4900000000-27a3388f44d41a748f99
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0490000000-558495048d959ca6d15b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-3becd4cabc167cbd5342
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0910000000-59be089c54a51a6fa68a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-a462d653725ff564df9c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-6910000000-220f5c5824aa6220985b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014m-9000000000-213bccb0adf86e0fab3c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.8214343
predicted
DarkChem Lite v0.1.0
[M-H]-165.2659343
predicted
DarkChem Lite v0.1.0
[M-H]-152.51418
predicted
DeepCCS 1.0 (2019)
[M+H]+165.5588343
predicted
DarkChem Lite v0.1.0
[M+H]+166.0506343
predicted
DarkChem Lite v0.1.0
[M+H]+154.87218
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.9384343
predicted
DarkChem Lite v0.1.0
[M+Na]+164.9848343
predicted
DarkChem Lite v0.1.0
[M+Na]+160.96538
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Mycobacterium fortuitum
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivativ...
Gene Name
sulI
Uniprot ID
Q49184
Uniprot Name
Dihydropteroate synthase type-1
Molecular Weight
30638.43 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. McDonald M, Mannion C, Rafter P: A confirmatory method for the simultaneous extraction, separation, identification and quantification of Tetracycline, Sulphonamide, Trimethoprim and Dapsone residues in muscle by ultra-high-performance liquid chromatography-tandem mass spectrometry according to Commission Decision 2002/657/EC. J Chromatogr A. 2009 Nov 13;1216(46):8110-6. doi: 10.1016/j.chroma.2009.05.092. Epub 2009 Jun 9. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data supported by the findings of 1 in vitro study.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Komatsu K, Ito K, Nakajima Y, Kanamitsu Si, Imaoka S, Funae Y, Green CE, Tyson CA, Shimada N, Sugiyama Y: Prediction of in vivo drug-drug interactions between tolbutamide and various sulfonamides in humans based on in vitro experiments. Drug Metab Dispos. 2000 Apr;28(4):475-81. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45