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SULFISOXAZOLE ACETYL (200 MG)

CAS：80-74-0
MW:309.3409
MF：C13H15N3O4S

Sulfisoxazole acetyl shares the actions and usesof the parent compound, sulfisoxazole. The acetyl derivativeis tasteless and, therefore, suitable for oral administration, especiallyin liquid preparations. The acetyl compound is splitin the intestinal tract and absorbed as sulfisoxazole; that is, itis a prodrug for sulfisoxazole. SULFISOXAZOLE ACETYL (200 MG) Preparation Products And Raw materials Raw materials View more+

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Names and ldentifier
Properties
Use and Manufacturing
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: SULFISOXAZOLE ACETYL (200 MG)

1.2 Synonyms: Acetamide, N-(3,4-dimethyl-5-isoxazolyl)-N-sulfanilyl-; Acetamide, N-[(4-aminophenyl)sulfonyl]-N-(3,4-dimethyl-5-isoxazolyl)-; Acetyl sulfisoxazole; Acetylgantrisin; Acetylsulfisoxazole; Gantrisin acetyl; Lipo Gantrisin; Lipo-Gantrisin; Lipo-Gantrisin acetyl; N-(3,4-Dimethyl-5-isoxazolyl)-N-sulfanilylacetamide; N-[(4-Aminophenyl)sulfonyl]-N-(3,4-dimethyl-5-isoxazolyl)acetamide; N′-Acetylsulfisoxazole; N1-Acetyl-N1-(3,4-dimethyl-5-isoxazolyl)sulfanilamide; N1-Acetylsulfisoxazole; N1-Monoacetylsulfisoxazole; n-3,4-dimethylisoxazol-5-yl-n-sulfanilylacetamide; N-Acetyl-4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide; N-Acetylsulfisoxazole; Sulfanilamide, N1-acetyl-N1-(3,4-dimethyl-5-isoxazolyl)-; Sulfazin; Sulfisoxazole Acetyl; SULFISOXAZOLE ACETYL (200 MG); Sulfisoxazole, N1-acetyl-;

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1.3 CAS No.: 80-74-0

1.4 CID: 6662

1.5 EINECS: 201-305-3

1.6 Molecular Formula: C13H15N3O4S

1.7 Inchi: 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

1.8 InChkey: JFNWFXVFBDDWCX-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(ON=C1C)N(C(=O)C)S(=O)(=O)C2=CC=C(C=C2)N

1.10 Isomers Smiles: CC1=C(ON=C1C)N(C(=O)C)S(=O)(=O)C2=CC=C(C=C2)N

2. Properties

2.1 Solubility: 80mg/L(37 ºC)

2.2 pKa: -0.17±0.10(Predicted)

2.3 Water Solubility: 80mg/L(37 oC)

3. Use and Manufacturing

3.1 Description: Sulfisoxazole acetyl is a sulfonamide and a member of benzenes.|Sulfisoxazole acetyl is an ester of sulfisoxazole, a broad-spectrum sulfanilamide and a synthetic analog of para-aminobenzoic acid (PABA) with antibacterial activity. Sulfisoxazole acetyl competes with PABA for the bacterial enzyme, dihydropteroate synthase, preventing the incorporation of PABA into dihydrofolic acid, which is the precursor of folic acid. This process causes an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, resulting in cell growth arrest and cell death. It is often combined with erythromycin to treat acute otitis media caused by the bacteria, haemophilus influenzae.|Sulfisoxazole Acetyl is an ester of sulfisoxazole, a broad-spectrum sulfanilamide and a synthetic analog of para-aminobenzoic acid (PABA) with antibacterial property. Sulfisoxazole acetyl competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.

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3.2 General Description: Sulfisoxazole acetyl shares the actions and usesof the parent compound, sulfisoxazole. The acetyl derivativeis tasteless and, therefore, suitable for oral administration, especiallyin liquid preparations. The acetyl compound is splitin the intestinal tract and absorbed as sulfisoxazole; that is, itis a prodrug for sulfisoxazole. SULFISOXAZOLE ACETYL (200 MG) Preparation Products And Raw materials Raw materials

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3.3 Usage: Antibacterial.

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

IR : KBr disc

IR : nujol mull

Mass

6. Synthesis Route

80-74-0Total: 1 Synthesis Route

127-69-5 86 Suppliers

108-24-7

80-74-0 14 Suppliers

7. Precursor and Product

precursor:

127-69-5

8. Computed Properties

Molecular Weight：309.3409g/mol
Molecular Formula：C₁₃H₁₅N₃O₄S
Compound Is Canonicalized：True
Exact Mass：1.3
XLogP3-AA：309.07832714
Monoisotopic Mass：309.07832714
Complexity：482
Rotatable Bond Count：3
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：6
Topological Polar Surface Area：115
Heavy Atom Count：：21
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBzOABAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABwAAAHgQUQAAADAiB3gAyxZJQAAKpAyVyUnDCABAlIgAomDk0bNoIJjrA0dOENYhmlDjIyUcQAAAIAAQAAAAAAAAACAAAAAAAAAAAAAAAAA==

9.Other Information

Collision Cross Section: 161.2 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Absorption: Readily absorbed from the gastrointestinal tract. In a pharmacokinetic study, the adjustments for variable renal clearances between oral and intravenous administration and using the unbound plasma concentrations, the bioavailability for an oral dose of sulfisoxazole was found to be 0.95 +/- 0.04.|The mean urinary excretion recovery following oral administration of sulfisoxazole is 97% within 48 hours, of which 52% is the parent drug, and the remaining as the N4-acetylated metabolite. It is excreted in human milk. Sulfisoxazole and its acetylated metabolites are excreted primarily by the kidneys through glomerular filtration.|The sulfonamides are widely distributed throughout all body tissues. It readily crosses the placental barrier and enters into fetal circulation and also crosses the blood-brain barrier. In healthy subjects, cerebrospinal fluid concentrations of sulfisoxazole vary; in patients with meningitis, however, concentrations of free drug in cerebrospinal fluid as high as 94 mcg/mL have been reported. In a pharmacokinetic study, the apparent volume of distribution for total drug was 10.9 +/- 2.0 liters and 136 +/- 36 liters for the unbound drug, indicating that sulfisoxazole is primarily distributed extracellularly.|The clearance of sulfisoxazole is 18.7 +/- 3.9 ml/min for total drug and 232 +/- 64 ml/min for the unbound drug.

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Metabolism: 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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