Identification

Name
Sulfapyridine
Accession Number
DB00891  (APRD00491)
Type
Small Molecule
Groups
Approved
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dagenan Tab 500mgTablet500 mgOralAventis Pharma Ltd.1992-12-312003-07-22Canada
Categories
UNII
Y5V2N1KE8U
CAS number
144-83-2
Weight
Average: 249.289
Monoisotopic: 249.057197301
Chemical Formula
C11H11N3O2S
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

Pharmacology

Indication

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

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
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Sulfapyridine.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sulfapyridine.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfapyridine.
AceclofenacThe metabolism of Aceclofenac can be decreased when combined 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.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Sulfapyridine.
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Sulfapyridine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfapyridine.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015028
KEGG Drug
D02434
PubChem Compound
5336
PubChem Substance
46506991
ChemSpider
5145
BindingDB
39340
ChEBI
132842
ChEMBL
CHEMBL700
Therapeutic Targets Database
DAP001200
PharmGKB
PA164779050
HET
SFY
Wikipedia
Sulfapyridine
ATC Codes
J01EB04 — SulfapyridineG01AE10 — Combinations of sulfonamides
PDB Entries
4hwk
MSDS
Download (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.
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)2.63ChemAxon
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-0090000000-6205fa17064877bf03df
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Aminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Pyridine / Organosulfonic acid amide / Imidolactam / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Aminosulfonyl compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
substituted 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 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. [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
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. [PubMed:10725317]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 04:52