4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide

• ChemBase ID: 6399
• Molecular Formular: C11H13N3O3S
• Molecular Mass: 267.30422
• Monoisotopic Mass: 267.06776229
• SMILES: S(=O)(=O)(Nc1oc(c(n1)C)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1oc(c(n1)C)C
• InChI: InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)
• InChIKey: CYFLXLSBHQBMFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfamoxole
• Brand Name: Sulfavigor; Justamil; Sulfmidil; Tardamid; Vetranal; Nuprin
• Synonyms: Sulphamoxole; Sulfamoxol; Sulfamoxolum; Sulfono; Sulfamoxole; N1-(4,5-dimethyl-2-oxazolyl)sulfanilamide; 2-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazole; 2-Sulfanilamido-4,5-dimethyloxazole; Justamil; NSC 683535; N'-(4,5-Dimethyl-2-oxazolyl)sulfanilamide; Oxasulfa; Sulfabutin; Sulfadimethyloxazole; Sulfano; Sulfavigor; Sulfmidil; Sulfune; Sulfuno; Tardamid; Tardamide; 4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide; N1-(4,5-Dimethyloxazol-2-yl)sulfanilamide; Sulfamoxole; 4-氨基-N-(4,5-二甲基-2-恶唑)苯磺酰胺; N1-(4,5-二甲基噁唑-2-基)磺胺; 磺胺噁唑

Database IDs

• CAS Number: 729-99-7
• EC Number: 211-982-7
• MDL Number: MFCD00005303
• Beilstein Number: 248434
• PubChem SID: 160969706; 24870529
• PubChem CID: 12894
• CHEBI ID: 55548
• ATC CODE: J01EC03
• Chemspider ID: 12361
• DrugBank ID: DB08798
• KEGG ID: D02516
• Unique Ingredient Identifier: HGG82XE020
• Wikipedia Title: Sulfamoxole

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8086896
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.57054317
• LogD (pH = 7.4): 0.058534656
• Log P: 0.58905804
• Molar Refractivity: 67.5145 cm^3
• Polarizability: 25.918407 Å^3
• Polar Surface Area: 98.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.04
• LOG S: -3.0
• Solubility (Water): 2.67e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 176-178°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: WO9150000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥80%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C11H13N3O3S

DETAILS

DrugBank - DB08798

• Drug Groups: approved
• Description: Sulfamoxole is a sulfonamide antibacterial.
• Indication: For the treatment of bacterial infection.
• Pharmacology: Sulfamoxole 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: Oral Rat LD50: > 12500 mg/kg; Intravenous Mouse LD50: 1 g/kg
• Affected Organisms: Enteric bacteria and other eubacteria
• References: DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 46866

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

Toronto Research Chemicals - S689010

Silversulfadiazine and Sulfamoxol are common drugs in treatment of bacterial disease.

REFERENCES

• DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. Pubmed
• Jaiswal, P., et al.: Talanta, 17, 236 (1970)
• Saxena, A., et al.: Prog. Drugs Res., 30, 221 (1970)