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

• ChemBase编号: 148
• 分子式: C11H13N3O3S
• 平均质量: 267.30422
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
• IUPAC传统名: ganda; 4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide; sulfisoxazole
• 商标名: 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
• 别名: 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; 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

登记号

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

理论计算性质

JChem

• Acid pKa: 5.804935
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.5794782
• LogD (pH = 7.4): -0.13589385
• Log P: 0.7306131
• 摩尔折射率: 67.9186 cm^3
• 极化性: 25.915007 Å^3
• 极化表面积: 98.22 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.14
• LOG S: -2.93
• 溶解度: 3.13e-01 g/l

分子性质

理化性质

• 溶解度: 0.13 mg/ml (25 oC)
• 熔点: 197-199°C
• 疏水性(logP): 0.9

安全信息

• 保存条件: -20°C; 2-8°C
• 保存注意事项: IRRITANT
• RTECS编号: WO9100000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: rat ... Ednra(24326)
• 生物活性机理: Folate antagonist; Restrict folate synthesis through competitive antagonism of PABA

产品相关信息

• 纯度: ≥99.0%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Antiseptic; Low acute toxicity; Protozoacide; Short-acting sulfonamide used for urinary tract infections.
• Empirical Formula (Hill Notation): C11H13N3O3S

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

参考文献

• 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