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- Acetyl sulfisoxazole
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Acetyl sulfisoxazole | CAS No: 80-74-0 | GMP-certified suppliers
A medication that treats acute and recurrent urinary tract infections, meningococcal meningitis, and acute otitis media caused by susceptible bacterial pathogens.
Therapeutic categories
AmidesAminesAniline CompoundsAnti-Bacterial AgentsBenzene DerivativesBenzenesulfonamides
Generic name
Acetyl sulfisoxazole
Molecule type
small molecule
CAS number
80-74-0
DrugBank ID
DB14033
Approval status
Approved drug, Vet_approved drug
ATC code
G01AE10
Primary indications
- Acute, recurrent or chronic urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) due to susceptible organisms (usually Escherichia coli, Klebsiella-Enterobacter, staphylococcus, Proteus mirabilis and, less frequently, Proteus vulgaris) in the absence of obstructive uropathy or foreign bodies
- Meningococcal meningitis where the organism has been demonstrated to be susceptible
- Haemophilus influenzae meningitis as adjunctive therapy with parenteral streptomycin
- Meningococcal meningitis prophylaxis
Product Snapshot
- Acetyl sulfisoxazole is an oral small molecule formulated as granules, suspension, and powder for suspension
- It is primarily indicated for the treatment of urinary tract infections, meningococcal and Haemophilus influenzae meningitis, as well as various adjunctive therapies including otitis media and malaria
- The compound is approved for use in the US and Canadian markets, including veterinary approvals
Clinical Overview
Acetyl sulfisoxazole, also known as sulfisoxazole acetyl, is an ester derivative of sulfisoxazole, a synthetic sulfanilamide antibiotic structurally related to para-aminobenzoic acid (PABA). It exhibits broad-spectrum antibacterial activity primarily by inhibiting bacterial folic acid synthesis. This inhibition occurs through competitive binding to the bacterial enzyme dihydropteroate synthase, preventing the incorporation of PABA into dihydrofolic acid, a critical precursor for folic acid production. This mechanism disrupts the synthesis of purines and pyrimidines, essential for DNA and RNA production, leading to bacterial cell growth arrest and ultimately cell death.
Clinically, acetyl sulfisoxazole is indicated for the treatment of acute, recurrent, or chronic urinary tract infections caused by susceptible pathogens such as Escherichia coli, Klebsiella-Enterobacter species, Staphylococcus species, and Proteus mirabilis. It is also employed in meningococcal meningitis where susceptibility is confirmed, Haemophilus influenzae meningitis as adjunctive therapy with parenteral streptomycin, and meningococcal meningitis prophylaxis. Additionally, it is used in combination with erythromycin or penicillin for acute otitis media due to Haemophilus influenzae. Other adjunctive uses include trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis with pyrimethamine, and chloroquine-resistant malaria. However, resistance among pathogens has increasingly limited its utility, particularly in chronic or recurrent urinary tract infections.
Pharmacodynamically, acetyl sulfisoxazole is bacteriostatic and broadly active against many gram-positive and gram-negative bacteria. Resistance to one sulfonamide generally predicts resistance to all within this class. Due to its physicochemical properties, it achieves effective concentrations in cerebrospinal fluid during meningeal infections; however, antibacterial activity may be impaired by the presence of pus.
The compound belongs to aminobenzenesulfonamides and acts as a weak inhibitor of cytochrome P450 CYP2C9 enzymes, which may impact drug interaction profiles. Approved for human and veterinary use in various jurisdictions, it is available under several formulations, often in combination with other antimicrobials.
From an ADME perspective, acetyl sulfisoxazole is partially acetylated in vivo. Relevant pharmacokinetic parameters such as absorption, distribution, metabolism, and excretion underpin its clinical use but may vary depending on formulation and patient factors.
Safety considerations include hypersensitivity reactions common to sulfonamide compounds, potential for hematological toxicity, and contraindications in patients with known sulfonamide allergies. Careful consideration is necessary for populations with renal impairment or predisposing conditions.
Sourcing of acetyl sulfisoxazole API requires verification of purity, consistent acetylation, and compliance with pharmacopeial standards. Authenticity and stability under storage conditions must be ensured to maintain efficacy and safety. Working with manufacturers who provide comprehensive analytical documentation and batch-to-batch consistency is critical for pharmaceutical development and regulatory compliance.
Clinically, acetyl sulfisoxazole is indicated for the treatment of acute, recurrent, or chronic urinary tract infections caused by susceptible pathogens such as Escherichia coli, Klebsiella-Enterobacter species, Staphylococcus species, and Proteus mirabilis. It is also employed in meningococcal meningitis where susceptibility is confirmed, Haemophilus influenzae meningitis as adjunctive therapy with parenteral streptomycin, and meningococcal meningitis prophylaxis. Additionally, it is used in combination with erythromycin or penicillin for acute otitis media due to Haemophilus influenzae. Other adjunctive uses include trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis with pyrimethamine, and chloroquine-resistant malaria. However, resistance among pathogens has increasingly limited its utility, particularly in chronic or recurrent urinary tract infections.
Pharmacodynamically, acetyl sulfisoxazole is bacteriostatic and broadly active against many gram-positive and gram-negative bacteria. Resistance to one sulfonamide generally predicts resistance to all within this class. Due to its physicochemical properties, it achieves effective concentrations in cerebrospinal fluid during meningeal infections; however, antibacterial activity may be impaired by the presence of pus.
The compound belongs to aminobenzenesulfonamides and acts as a weak inhibitor of cytochrome P450 CYP2C9 enzymes, which may impact drug interaction profiles. Approved for human and veterinary use in various jurisdictions, it is available under several formulations, often in combination with other antimicrobials.
From an ADME perspective, acetyl sulfisoxazole is partially acetylated in vivo. Relevant pharmacokinetic parameters such as absorption, distribution, metabolism, and excretion underpin its clinical use but may vary depending on formulation and patient factors.
Safety considerations include hypersensitivity reactions common to sulfonamide compounds, potential for hematological toxicity, and contraindications in patients with known sulfonamide allergies. Careful consideration is necessary for populations with renal impairment or predisposing conditions.
Sourcing of acetyl sulfisoxazole API requires verification of purity, consistent acetylation, and compliance with pharmacopeial standards. Authenticity and stability under storage conditions must be ensured to maintain efficacy and safety. Working with manufacturers who provide comprehensive analytical documentation and batch-to-batch consistency is critical for pharmaceutical development and regulatory compliance.
Identification & chemistry
| Generic name | Acetyl sulfisoxazole |
|---|---|
| Molecule type | Small molecule |
| CAS | 80-74-0 |
| UNII | WBT5QH3KED |
| DrugBank ID | DB14033 |
Pharmacology
| Summary | Sulfisoxazole is a sulfonamide antibiotic that acts as a competitive inhibitor of the bacterial enzyme dihydropteroate synthase, blocking folic acid synthesis by preventing the incorporation of para-aminobenzoic acid (PABA). This disruption of folate metabolism exerts bacteriostatic effects against a broad spectrum of gram-positive and gram-negative organisms. Its primary therapeutic applications include treatment of urinary tract infections and certain bacterial meningitis cases caused by susceptible pathogens. |
|---|---|
| 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 . |
| 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 . |
Targets
| Target | Organism | Actions |
|---|---|---|
| Dihydropteroate synthase | Escherichia coli (strain K12) | inhibitor |
ADME / PK
| 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 . |
|---|---|
| Half-life | The serum half-life is 10 -12 hours . |
| Protein binding | Approximately 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 . |
| 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 . |
| Route of elimination | 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 . |
| Volume of distribution | 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 . |
| Clearance | The clearance of sulfisoxazole is 18.7 +/- 3.9 ml/min for total drug and 232 +/- 64 ml/min for the unbound drug . |
Formulation & handling
- Acetyl sulfisoxazole is a small molecule intended for oral administration, commonly formulated as suspensions or granules for reconstitution.
- The compound exhibits moderate water solubility (0.136 g/L) and low lipophilicity (LogP 0.72), which should be considered in formulation for bioavailability optimization.
- Stability and handling conditions should ensure protection from moisture due to its solid state and formulation as powders and granules for suspension.
Regulatory status
| Lifecycle | The API has patent protection expired in the US and Canada, with generic versions available, indicating a mature market phase characterized by established competition and standardized therapeutic use. |
|---|
| Markets | US, Canada |
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Supply Chain
| Supply chain summary | The manufacturing and supply landscape for Acetyl sulfisoxazole involves multiple originator companies producing branded combination products such as Erythromycin Ethylsuccinate and Sulfisoxazole Acetyl, with market presence primarily in the US and Canada. These branded products have an established footprint in North America, while patent expirations suggest that generic competition is currently present or imminent in these markets. |
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Safety
| Toxicity | LD<sub>50</sub>=6800 mg/kg (Orally in mice) . Sulfonamide-induced hypersensitivity reactions, although uncommon, can be severe. They can include rare life-threatening cutaneous reactions such as erythema multiform (Stevens-Johnson syndrome) and toxic epidermal necrolysis. Crystalluria may result in dysuria, renal colic, haematuria and acute renal obstruction . Other infrequent reactions include granulocytopenia, agranulocytosis, aplastic anemia, thrombocytopenic purpura and toxic hepatitis. Rarely, hemolysis may occur in individuals deficient in glucose-6-phosphate dehydrogenase . The severe or irreversible adverse effects of sulfisoxazole, which give rise to more complications which may include: nephrotoxicity, blood dyscrasias, interstitial nephritis, hematuria, crystalluria, oliguria, anuria, lumbar pain, and tubular necrosis . The symptomatic adverse reactions produced by sulfisoxazole are more or less tolerable and if severe, may be treated symptomatically, these include anorexia, diarrhea, rashes, pruritus, nausea and vomiting, hypersensitivity reactions, Photosensitivity reactions . **Overdosage:** Continuously forced diuresis may be beneficial and an alkaline urine should be initiated . |
|---|
High Level Warnings:
- Sulfonamide compounds may induce rare but severe hypersensitivity reactions, including Stevens-Johnson syndrome and toxic epidermal necrolysis
- Risk of crystalluria exists, potentially leading to renal complications such as obstruction and acute nephrotoxicity
- Infusion may cause hematologic adverse effects, including granulocytopenia, agranulocytosis, aplastic anemia, and hemolysis in G6PD-deficient individuals
Acetyl sulfisoxazole is a type of Antibacterials
Antibacterials, a category of pharmaceutical active pharmaceutical ingredients (APIs), play a crucial role in combating bacterial infections. These APIs are chemical compounds that target and inhibit the growth or kill bacteria, helping to eliminate harmful bacterial pathogens from the body.
Antibacterials are essential for the treatment of various bacterial infections, including respiratory tract infections, urinary tract infections, skin and soft tissue infections, and more. They are commonly prescribed by healthcare professionals to combat both mild and severe bacterial infections.
Within the category of antibacterials, there are different classes and subclasses of APIs, each with distinct mechanisms of action and target bacteria. Some commonly used antibacterials include penicillins, cephalosporins, tetracyclines, macrolides, and fluoroquinolones. These APIs work by interfering with various aspects of bacterial cellular processes, such as cell wall synthesis, protein synthesis, DNA replication, or enzyme activity.
The development and production of antibacterial APIs require stringent quality control measures to ensure their safety, efficacy, and purity. Pharmaceutical manufacturers must adhere to Good Manufacturing Practices (GMP) and follow rigorous testing protocols to guarantee the quality and consistency of these APIs.
As bacterial resistance to antibiotics continues to be a significant concern, ongoing research and development efforts aim to discover and develop new antibacterial APIs. The evolution of antibacterials plays a crucial role in combating emerging bacterial strains and ensuring effective treatment options for infectious diseases.
In summary, antibacterials are a vital category of pharmaceutical APIs used to treat bacterial infections. They are designed to inhibit or kill bacteria, and their development requires strict adherence to quality control standards. By continually advancing research in this field, scientists and pharmaceutical companies can contribute to the ongoing battle against bacterial infections.
