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
Structure for Sulfapyridine (DB00891)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism UDihydropteroate synthase type-1 inhibitorMycobacterium 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50 is 15800 mg/kg (orally in rats).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbrocitinib The metabolism of Abrocitinib can be decreased when combined with Sulfapyridine. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfapyridine. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Sulfapyridine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Sulfapyridine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfapyridine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dagenan Tab 500mg Tablet 500 mg Oral Aventis Pharma Ltd. 1992-12-31 2003-07-22 Canada 
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Benzene Derivatives
- Benzenesulfonamides
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Methemoglobinemia Associated Agents
- Short-Acting Antibacterial Sulfonamides
- Sulfanilamides
- Sulfonamides
- Sulfonamides and trimethoprim
- Sulfones
- Sulfur Compounds
- 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
- External Links
- Human Metabolome Database
- HMDB0015028
- KEGG Drug
- D02434
- PubChem Compound
- 5336
- PubChem Substance
- 46506991
- ChemSpider
- 5145
- BindingDB
- 39340
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Eli lilly and co
- Packagers
- Amend
- Prime European Therapeuticals SPA
- Dosage Forms
Form Route Strength Tablet Oral 500 mg - Prices
Unit description Cost Unit Sulfapyridine powder 0.13USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 192 °C PhysProp water solubility 268 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.35 HANSCH,C ET AL. (1995) logS -2.7 ADME Research, USCD pKa 8.43 PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 0.235 mg/mL ALOGPS logP 0.84 ALOGPS logP 1.01 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 6.24 Chemaxon pKa (Strongest Basic) 2.14 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 85.08 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 65.75 m3·mol-1 Chemaxon Polarizability 24.97 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9884 Blood Brain Barrier + 0.9552 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.8936 P-glycoprotein inhibitor I Non-inhibitor 0.9418 P-glycoprotein inhibitor II Non-inhibitor 0.9009 Renal organic cation transporter Non-inhibitor 0.8822 CYP450 2C9 substrate Non-substrate 0.7789 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7808 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9389 CYP450 2C19 inhibitor Non-inhibitor 0.953 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7533 Ames test Non AMES toxic 0.9347 Carcinogenicity Non-carcinogens 0.9209 Biodegradation Not ready biodegradable 0.992 Rat acute toxicity 1.2293 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.921 hERG inhibition (predictor II) Non-inhibitor 0.8512
Spectra
- Mass Spec (NIST)
- Download (8.66 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 164.8214343 predictedDarkChem Lite v0.1.0 [M-H]- 165.2659343 predictedDarkChem Lite v0.1.0 [M-H]- 152.51418 predictedDeepCCS 1.0 (2019) [M+H]+ 165.5588343 predictedDarkChem Lite v0.1.0 [M+H]+ 166.0506343 predictedDarkChem Lite v0.1.0 [M+H]+ 154.87218 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.9384343 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.9848343 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.96538 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- 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