Grundinformationen
- CAS
80-74-0- Standard-SMILES
CC(=O)N(c1onc(C)c1C)S(=O)(=O)c1ccc(N)cc1- InChIKey
JFNWFXVFBDDWCX-UHFFFAOYSA-N- Summenformel
- C13H15N3O4S
- Durchschnittliche Molmasse
- 309,34 g/mol
- Monoisotopische Masse
- 309,07832714
Überblick
Sulfisoxazole acetyl is a member of benzenes and a sulfonamide.
Namen und Bezeichner
- Bevorzugter Name
- Sulfisoxazole Acetyl
- IUPAC
- N-(4-aminophenyl)sulfonyl-N-(3,4-dimethyl-1,2-oxazol-5-yl)acetamide
- Lokaler Name
- N-3,4-Dimethylisoxazol-5-yl-N-sulfanilylacetamid
- Englischer Name
- SULFISOXAZOLE ACETYL (200 MG)
- Summenformel
- C13H15N3O4S
- Molmasse
- 309.3409
Namen und Synonyme
Sulfisoxazole acetyl80-74-0ACETYL SULFISOXAZOLELipo GantrisinacetylsulfafurazoleAcetylsulfisoxazoleGANTRISIN PEDIATRICAcetyl sulfafurazoleSulfafurazole acetylSulfisoxizole acetylWBT5QH3KEDNSC-759138
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
80-74-0- PubChem CID
- 6662
- DTXSID
DTXSID4023620- ChEMBL
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,3
- Polarare Oberfläche (TPSA)
- 115 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 482
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 193 · 193-194°
- Siedepunkt
- 538.1 · 538.1±60.0 °C(Predicted)
- Dichte
- 1.3541 · 1.3541 (rough estimate)
- Brechungsindex
- 1.632 · 1.6320 (estimate)
- pka
- -0.17 · -0.17±0.10(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to off-white
- Wasserlöslichkeit
- 80 mg/L · 80mg/L(37 ºC)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- hs_code
- 2935904000
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
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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