4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide

• ChemBase ID: 148
• Molecular Formular: C11H13N3O3S
• Molecular Mass: 267.30422
• Monoisotopic Mass: 267.06776229
• SMILES: S(=O)(=O)(Nc1onc(c1C)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1onc(c1C)C
• InChI: InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
• InChIKey: NHUHCSRWZMLRLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
• IUPAC Traditional name: ganda; 4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide; sulfisoxazole
• Brand Name: Accuzole; Alphazole; Amidoxal; Astrazolo; Azo Gantrisin; Azosulfizin; Bactesulf; Barazae; Chemouag; Cosoxazole; Dorsulfan; Dorsulfan Warthausen; Entusil; Entusul; G-Sox; Ganda; Gantrisin; Gantrisine; Gantrisona; Gantrosan; Isoxamin; J-Sul; Koro-Sulf; Neazolin; Neoxazol; Norilgan-S; Novazolo; Novosaxazole; Pancid; Renosulfan; Resoxol; Roxosul; Roxosul Tablets; Roxoxol; SI; Saxosozine; Sk-Soxazole; Sodizole; Sosol; Soxamide; Soxazole; Soxisol; Soxitabs; Soxo; Soxomide; Stansin; Sulbio; Sulfagan; Sulfagen; Sulfalar; Sulfapolar; Sulfasan; Sulfasol; Sulfazin; Sulfisin; Sulfizin; Sulfizol; Sulfizole; Sulfoxol; Suloxsol; Sulphafuraz; Sulsoxin; Thiasin; Tl-Azole; Unisulf; Urisoxin; Uritrisin; Urogan; V-Sul; Vagilia
• Synonyms: N1-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide; Sulfisoxazole; 5-Sulfanilamido-3,4-dimethyl-isoxazole; Accuzole; Amidoxal; 4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide; N^1-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide; Gantrisin Pediatric; 4-Amino-N-(3,4-dimethylisoxazol-5-yl)-benzenesulfonamide; Sulfisoxazole; Gantrisin; Soxomide; Thiasin; Neoxazol; Sulfafurazole; Sulfadimethylisoxazole; Sulfafurazol; Sulfafurazole; Sulfaisoxazole; Sulfasoxazole; Sulfisoxazole Dialamine; Sulfisoxasole; Sulfisoxazol; Sulfisoxazole Diolamine; Sulphafurazol; Sulphafurazolum; Sulphafurazole; Sulphofurazole; Sulphisoxazol; Sulphaisoxazole; Sulfofurazole; Sulfisonazole; Sulfisoxazole; 4-氨基-N-(3,4-二甲基-5-异噁唑基)苯磺酰胺; N1-(3,4-二甲基-5-异噁唑基)磺胺; 磺胺异噁唑

Database IDs

• CAS Number: 127-69-5
• EC Number: 204-858-9
• MDL Number: MFCD00003150
• Beilstein Number: 6737262
• PubChem SID: 24870567; 24899697; 46505342; 160963611
• PubChem CID: 5344

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.804935
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5794782
• LogD (pH = 7.4): -0.13589385
• Log P: 0.7306131
• Molar Refractivity: 67.9186 cm^3
• Polarizability: 25.915007 Å^3
• Polar Surface Area: 98.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.14
• LOG S: -2.93
• Solubility (Water): 3.13e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.13 mg/ml (25 oC)
• Melting Point: 197-199°C
• Hydrophobicity(logP): 0.9

Safety Information

• Storage Condition: -20°C; 2-8°C
• Storage Warning: IRRITANT
• RTECS: WO9100000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Ednra(24326)
• Mechanism of Action: Folate antagonist; Restrict folate synthesis through competitive antagonism of PABA

Product Information

• Purity: ≥99.0%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Antiseptic; Low acute toxicity; Protozoacide; Short-acting sulfonamide used for urinary tract infections.
• Empirical Formula (Hill Notation): C11H13N3O3S

DETAILS

MP Biomedicals - 02102993

Crystalline

DrugBank - DB00263

• Drug Groups: approved
• Description: A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms. [PubChem]
• Indication: For the treatment of severe, repeated, or long-lasting urinary tract infections, meningococcal meningitis, acute otitis media, trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis, malaria and other bacterial infections.
• Pharmacology: Sulfisoxazole 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=6800 mg/kg (Orally in mice)
• Affected Organisms: Enteric bacteria and other eubacteria
• Elimination: The mean urinary excretion recovery following oral administration of sulfisoxazole is 97% within 48 hours, of which 52% is intact drug, with the remaining as the N4-acetylated metabolite. It is excreted in human milk.
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1916

Research Area: Infection
Biological Activity:
Sulfisoxazole is a sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of Gram-negative and Gram-positive organisms. It is sometimes given in combination with erythromycin or phenazopyridine. It is used locally in a 4% solution or ointment. [1]

Sigma Aldrich - S6377

Biochem/physiol Actions
Selective ETA antagonist.

Sigma Aldrich - 31739

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

REFERENCES

• http://en.wikipedia.org/wiki/Sulfafurazole
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 101A, (nmr)
• Hoeprich, P.D., Antimicrob. Agents Chemother., 1967, 697, (pharmacol)
• Rudy, B.C. et al., Anal. Profiles Drug Subst., 1973, 2, 487, (rev, synth)
• Manzo, R.H. et al., J. Pharm. Sci., 1973, 62, 152, (uv)
• IARC Monog., 1980, 24, 275; Suppl. 7, 347; Suppl. 6, 502, (rev, tox)
• Chatterjee, C. et al., Acta Cryst. B, 1982, 38, 1845, (cryst struct)
• Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1971
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 876, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 207
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SNN500