基本情報
- CAS
80-74-0- 標準SMILES
CC(=O)N(c1onc(C)c1C)S(=O)(=O)c1ccc(N)cc1- InChIKey
JFNWFXVFBDDWCX-UHFFFAOYSA-N- 分子式
- C13H15N3O4S
- 平均分子量
- 309.34 g/mol
- 単同位体質量
- 309.07832714
概要
Sulfisoxazole acetyl is a member of benzenes and a sulfonamide.
名称と識別子
- 優先名称
- Sulfisoxazole Acetyl
- IUPAC
- N-(4-aminophenyl)sulfonyl-N-(3,4-dimethyl-1,2-oxazol-5-yl)acetamide
- 現地名
- アセチルスルフイソキサゾール
- 英語名
- SULFISOXAZOLE ACETYL (200 MG)
- 分子式
- C13H15N3O4S
- 分子量
- 309.3409
名称と別名
Sulfisoxazole acetyl80-74-0ACETYL SULFISOXAZOLELipo GantrisinacetylsulfafurazoleAcetylsulfisoxazoleGANTRISIN PEDIATRICAcetyl sulfafurazoleSulfafurazole acetylSulfisoxizole acetylWBT5QH3KEDNSC-759138
名称をさらに表示
N-(3,4-ジメチル-5-イソオキサゾリル)-N-スルファニリルアセトアミドスルフィソキサゾールアセチルリポガントリシンアセチルスルフィソキサゾール5-[N-アセチル-N-(p-アミノフェニルスルホニル)アミノ]-3,4-ジメチルイソオキサゾールN-(4-アミノフェニルスルホニル)-N-(3,4-ジメチル-5-イソオキサゾリル)アセトアミドスルフイソキサゾールアセチルアセチルスルフイソキサゾールアセチルスルフイソキサゾール (JAN)N-(4-アミノベンゼンスルホニル)-N-(3,4-ジメチル-1,2-オキサゾール-5-イル)アセトアミドASIZN1-AcetylsulfisoxazoleSULFISOXAZOLE ACETYL (200 MG)Sulfisoxazole Acetyl (1639003)1-(oxazol-2-ylsulfinyl)ethanone
Sulfisoxazole acetyl (USP)Sulfisoxazole acetyl [USP]N-3,4-Dimethylisoxazol-5-yl-N-sulphanilylacetamideAcetamide, N-((4-aminophenyl)sulfonyl)-N-(3,4-dimethyl-5-isoxazolyl)-N-(4-aminobenzenesulfonyl)-N-(3,4-dimethyl-1,2-oxazol-5-yl)acetamideAcetamide, N-[(4-aminophenyl)sulfonyl]-N-(3,4-dimethyl-5-isoxazolyl)-RefChem:56070201-305-3
物性
構造計算による物性
- XLogP
- 1.3
- 極性表面積
- 115 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 6
- 回転可能結合数
- 3
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 482
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section161.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 193 · 193-194°
- 沸点
- 538.1 · 538.1±60.0 °C(Predicted)
- 比重(密度)
- 1.3541 · 1.3541 (rough estimate)
- 屈折率
- 1.632 · 1.6320 (estimate)
- 酸解離定数(Pka)
- -0.17 · -0.17±0.10(Predicted)
- 外見
- Solid
- 色
- White to off-white
- 水溶解度
- 80 mg/L · 80mg/L(37℃)
- 主な用途
- 医薬品（低分子化合物）
- InChI
- 1S/C13H15N3O4S/c1-8-9(2)15-20-13(8)16(10(3)17)21(18,19)12-6-4-11(14)5-7-12/h4-7H,14H2,1-3H3
- InChIKey
- JFNWFXVFBDDWCX-UHFFFAOYSA-N
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- wgk
- WGK 3
- hs_code
- 2935904000
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Protein BindingApproximately 85% of a dose of sulfisoxazole is bound to plasma proteins, primarily to albumin; 65% to 72% of the unbound portion is in the nonacetylated form.
Pharmacodynamics
Sulfisoxazole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with action against most gram-positive and many gram-negative organisms. Many strains of an individual species may be resistant to this drugf. Sulfonamides inhibit the multiplication of bacteria by acting as competitive inhibitors of <i>p</i>-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. 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
Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Biological Half-LifeThe serum half-life is 10 -12 hours.
Metabolism/Metabolites
Sulfisoxazole acetyl is a prodrug of _sulfisoxazole_. The acetyl group is added to make the drug poorly water-soluble and is hydrolyzed in vivo to the active drug,. N1-acetyl sulfisoxazole is metabolized to sulfisoxazole by digestive enzymes in the gastrointestinal tract and is absorbed as sulfisoxazole. This enzymatic splitting is thought to be responsible for slower absorption and lower peak blood concentrations are achieved after administration of an equal oral dose of sulfisoxazole. With sustained administration of acetyl sulfisoxazole, blood concentrations approximate those of sulfisoxazole. Following a single 4 gram dose of acetyl sulfisoxazole to healthy volunteers, maximum plasma concentrations of sulfisoxazole ranged from 122 to 282 mcg/mL (mean, 181 mcg/mL) for the pediatric suspension and occurred between 2 and 6 hours postadministration of sulfisoxazole, in a pharmacokinetic study.
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