4-amino-N-(pyridin-2-yl)benzene-1-sulfonamide

• ChemBase ID: 768
• Molecular Formular: C11H11N3O2S
• Molecular Mass: 249.28894
• Monoisotopic Mass: 249.05719761
• SMILES: S(=O)(=O)(Nc1ncccc1)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1ccccn1
• 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)
• InChIKey: GECHUMIMRBOMGK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(pyridin-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: ronin; sulfapyridine
• Brand Name: Adiplon; Coccoclase; Dagenan; Eubasin; Eubasinum; Haptocil; M and B 693; Piridazol; Plurazol; Pyriamid; Pyridazol; Relbapiridina; Ronin; Septipulmon; Streptosilpyridine; Sulfidin; Sulfidine; Thioseptal; Trianon
• Synonyms: 4-Amino-N-2-pyridinyl-benzenesulfonamide; N^1-(Pyridin-2-yl)sulfanilamide; 4-Amino-N-pyridin-2-ylbenzenesulfonamide; 4-Amino-N-[2-pyridyl]benzene sulfonamide; N1-(Pyridin-2-yl)sulfanilamide; Sulfapyridine; Sulfapyridine (Dagenan); 4-(2-Pyridinylsulfonyl)aniline; 4-[(2-Pyridylamino)sulfonyl]aniline; N(sup 1)-2-Pyridylsulfanilamide; N(sup1)-Pyridylsulfanilamide; N-2-Pyridylsulfanilamide; N1-2-Pyridylsulfanilamide; Sulphapyridine; Sulfapyridine; 2-Sulfanilamidopyridin; 2-Sulfanilamidopyridine; 2-Sulfanilylaminopyridine; 2-Sulfapyridine; 4-Amino-N-2-pyridinylbenzenesulfonamide; Adiplon; Coccoclase; Dagenan; Eubasin; Eubasinum; Haptocil; Sulfidine; Thioseptal; Trianon; 4-氨基-N-[2-吡啶基]苯磺酰胺; N1-(吡啶-2-基)磺胺; 磺胺吡啶

Database IDs

• CAS Number: 144-83-2; 144-83-2
• EC Number: 205-642-7
• MDL Number: MFCD00038036
• Beilstein Number: 222065
• PubChem SID: 24870540; 24899692; 160964231; 46506991
• PubChem CID: 5336
• CHEBI ID: 132842
• ATC CODE: QJ01EQ04; J01EB04
• CHEMBL: 700
• Chemspider ID: 5145
• DrugBank ID: DB00891
• KEGG ID: D02434
• Unique Ingredient Identifier: Y5V2N1KE8U
• Wikipedia Title: Sulfapyridine
• Medline Plus: a682204

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.2384915
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.94377524
• LogD (pH = 7.4): 0.24198662
• Log P: 1.0087702
• Molar Refractivity: 65.7472 cm^3
• Polarizability: 25.447033 Å^3
• Polar Surface Area: 85.08 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.84
• LOG S: -3.03
• Solubility (Water): 2.35e-01 g/l

PROPERTIES

Physical Property

• Solubility: 268 mg/L; Dimethyl Sulfoxide; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 194-196°C
• Hydrophobicity(logP): 0.9

Safety Information

• Storage Condition: 2-8°C, Protect from light; Refrigerator, Under Inert Atmosphere
• Storage Warning: 2-80C; IRRITANT
• RTECS: DA9625000
• German water hazard class: 2
• TSCA Listed: false
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥99.0%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Pharmacopeia Traceability: traceable to USP 1635002
• Empirical Formula (Hill Notation): C11H11N3O2S

DETAILS

MP Biomedicals - 02102991

Crystalline

DrugBank - DB00891

• Drug Groups: approved
• Description: Antibacterial, potentially toxic, used to treat certain skin diseases. [PubChem]
• Indication: For the treatment of dermatitis herpetiformis, benign mucous membrane pemphigoid and pyoderma gangrenosum
• Pharmacology: 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.
• Toxicity: LD₅₀ is 15800 mg/kg (orally in rats).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Approximately 60-80%
• Half Life: 6-14 hours.
• Protein Binding: Approximately 50% bound to plasma proteins.
• External Links: Wikipedia

Sigma Aldrich - 31738

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699083

Used in treatment of dermatitis herpetiformis; antibacterial.

REFERENCES

• Wien, R., et al.: J. Pharmacol. Exp. Ther., 84, 211 (1945)
• Stone, O.J., et al.: Med. Hypotheses, 31, 99 (1945)
• Elder, M.J., et al.: Br. J. Ophthalmol., 80, 549 (1945)