Identification
NameSulfapyridine
Accession NumberDB00891  (APRD00491)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
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
Streptosilpyridine
Sulfapiridina
Sulfapyridin
Sulfapyridine
Sulfapyridinum
Sulphapyridine
External IDs M & B 693 / N000159
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dagenan Tab 500mgTablet500 mgOralAventis Pharma Ltd.1992-12-312003-07-22Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIY5V2N1KE8U
CAS number144-83-2
WeightAverage: 249.289
Monoisotopic: 249.057197301
Chemical FormulaC11H11N3O2S
InChI KeyGECHUMIMRBOMGK-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
Pharmacology
Indication

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

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Dihydropteroate synthase type-1Proteinunknown
inhibitor
Mycobacterium fortuitumQ49184 details
Related Articles
Absorption

Approximately 60-80%

Volume of distributionNot Available
Protein binding

Approximately 50% bound to plasma proteins.

Metabolism

Hepatic.

Route of eliminationNot Available
Half life

6-14 hours.

ClearanceNot Available
Toxicity

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

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfapyridine.Approved
MecamylamineThe risk or severity of adverse effects can be increased when Sulfapyridine is combined with Mecamylamine.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01EB04 — SulfapyridineG01AE10 — Combinations of sulfonamides
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.8 KB)
Clinical Trials
Clinical Trials Not Available
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.
PatentsNot Available
Properties
StateSolid
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)2.63ChemAxon
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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a59-4920000000-ddd28eca3499faaddfb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-76404b7958aaaddb00c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-b794dcd70eedfd04a9e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-1690000000-d32f010faae95dd6e5ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-b89b3d587bf8893e343aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-7900000000-e9c1ce1a2bfb8587016bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052f-9600000000-c2b3b96e2d3db5fc940fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-9400000000-6eeb6714b222ec20731eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-14bd7d3423dbbc1677f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-1690000000-ec5ad1677ec436c15076View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-3221fbcec55c511e58a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-7900000000-4959721f5e57ee1708c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052f-9600000000-cb7f712bbbba5e75ed73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-9400000000-542a7f83b7c124aeaa3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-ebce9cc4e8380518ddecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-5900000000-c36697c8e5b4522ccfc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052f-9600000000-07faf61cc06e82c703a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-2ae47a77fd32fcf2200eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-4653688bc5b5c91f5a27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminobenzenesulfonamides
Alternative ParentsBenzenesulfonyl compounds / Aniline and substituted anilines / Pyridines and derivatives / Primary aromatic amines / Organosulfonamides / Imidolactams / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds
SubstituentsAminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Primary aromatic amine / Pyridine / Organosulfonic acid amide / Imidolactam / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorssubstituted aniline, sulfonamide, pyridines, sulfonamide antibiotic (CHEBI:132842 )

Targets

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 derivatives (By similarity). Implicated in resistance to sulfonamide (PubMed:2163027).
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:19586630 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Uniprot Name:
Cytochrome P450 2C9
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:54