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Acetohydroxamic acid | CAS No: 546-88-3 | GMP-certified suppliers
A medication that serves as an adjunctive treatment for chronic urea-splitting urinary infections, enhancing antibiotic efficacy by inhibiting bacterial urease activity.
Therapeutic categories
Primary indications
- Used, in addition to antibiotics or medical procedures, to treat chronic urea-splitting urinary infections
Product Snapshot
- Acetohydroxamic acid is available in multiple formulation types including oral tablets, injectable solutions, and otic solutions
- It is primarily utilized for adjunct treatment of chronic urea-splitting urinary infections alongside antibiotics or medical procedures
- This API is approved for use in the US market
Clinical Overview
Pharmacologically, acetohydroxamic acid functions as a reversible inhibitor of urease, a bacterial enzyme responsible for the hydrolysis of urea into ammonia and carbon dioxide in the urinary tract. By inhibiting urease activity, acetohydroxamic acid reduces the production of ammonia, which is otherwise associated with increased urinary pH and stone formation risk. This enzymatic inhibition leads to a lowered urinary pH and decreased ammonia concentration, thereby enhancing the efficacy of concurrent antimicrobial treatments. It is important to note that acetohydroxamic acid does not possess direct antimicrobial properties and does not acidify urine by itself.
Absorption, distribution, metabolism, and excretion (ADME) characteristics of acetohydroxamic acid are relevant primarily in the context of its urinary pharmacokinetics, as the drug must reach sufficient concentrations in the urine to inhibit bacterial urease effectively. Detailed ADME parameters are limited; however, renal elimination is the primary route for excretion, consistent with its site of action.
Safety considerations include careful monitoring for potential adverse effects, as urinary tract manipulation and urease inhibition can impact renal function and electrolyte balance. Toxicity profiles suggest that acetohydroxamic acid should be used with caution, particularly in patients with renal impairment or other comorbidities. Its use is generally reserved for cases where standard antimicrobial therapies are insufficient.
Notable product formulations containing acetohydroxamic acid have been approved for clinical use in various markets, primarily targeting refractory or complicated urinary infections involving urea-splitting organisms such as Proteus or Klebsiella species.
From an API sourcing perspective, ensuring pharmaceutical-grade purity and consistent inhibitory activity against urease is critical. Manufacturers and procurement teams should verify compliance with pharmacopeial standards and conduct rigorous quality control, including assays for potency, residual solvents, and impurity profiles, to maintain therapeutic reliability and safety.
Identification & chemistry
| Generic name | Acetohydroxamic acid |
|---|---|
| Molecule type | Small molecule |
| CAS | 546-88-3 |
| UNII | 4RZ82L2GY5 |
| DrugBank ID | DB00551 |
Pharmacology
| Summary | Acetohydroxamic Acid inhibits bacterial urease by reversibly binding to its active site, reducing urea hydrolysis and ammonia production in the urinary tract. This enzymatic inhibition lowers urine pH and ammonia levels, creating conditions that enhance the efficacy of concurrent antimicrobial treatments. The compound primarily targets urease subunit alpha and macrophage metalloelastase but lacks direct antimicrobial or urine acidifying effects. |
|---|---|
| Mechanism of action | Acetohydroxamic Acid reversibly inhibits the bacterial enzyme urease. This inhibits the hydrolysis of urea and production of ammonia in urine infected with urea-splitting organisms, leading to a decrease in pH and ammonia levels. As antimicrobial agents are more effective in such conditions, the effectiveness of these agents is amplified, resulting in a higher cure rate. |
| Pharmacodynamics | Acetohydroxamic Acid, a synthetic drug derived from hydroxylamine and ethyl acetate, is similar in structure to urea. In the urine, it acts as an antagonist of the bacterial enzyme urease. Acetohydroxamic Acid has no direct antimicrobial action and does not acidify urine directly. |
Targets
| Target | Organism | Actions |
|---|---|---|
| Urease subunit alpha | Enterobacter aerogenes | inhibitor |
| Macrophage metalloelastase | Humans | inhibitor |
ADME / PK
| Absorption | Well absorbed from the GI tract following oral administration. |
|---|---|
| Half-life | 5-10 hours in patients with normal renal function |
| Protein binding | No known binding |
| Metabolism | 35-65% of oral dose excreted unchanged in urine (which provides the drug's therapeutic effect). |
Formulation & handling
- Acetohydroxamic acid is a small molecule suitable for multiple administration routes, including oral, intravenous, parenteral, and auricular.
- Due to its chelating properties, avoid co-administration with iron supplements to prevent reduced bioavailability of both compounds.
- Administer on an empty stomach and avoid alcohol consumption to minimize adverse interactions and maintain stability.
Regulatory status
| Lifecycle | The API’s primary patents have expired in the US, leading to widespread availability of generic formulations. Market activity is now focused on established products with standard therapeutic use. |
|---|
| Markets | US |
|---|
Supply Chain
| Supply chain summary | Acetohydroxamic acid is manufactured and packaged primarily by a single originator company, Mission Pharmacal Co, with branded products such as Lithostat marketed mainly in the US. The limited manufacturer presence and market focus suggest a concentrated supply landscape. There is no data indicating significant patent expiration, implying limited or no generic competition currently. |
|---|
Safety
| Toxicity | Oral, rat: LD<sub>50</sub> = 4.8gm/kg. Symptoms of overdose include anorexia, malaise, lethargy, diminished sense of wellbeing, tremor, anxiety, nausea, and vomiting. |
|---|
- Oral LD50 in rats is 4
- 8 g/kg, indicating moderate acute toxicity
- Overdose may induce neurological and gastrointestinal symptoms including tremor, anxiety, nausea, and vomiting
Acetohydroxamic Acid is a type of Other antibacterials
The category of pther antibacterials in the pharmaceutical API (Active Pharmaceutical Ingredient) industry encompasses a diverse range of antibacterial substances that are not classified under specific subcategories. These APIs exhibit potent antibacterial activity against various bacteria and play a crucial role in combating bacterial infections.
The Other antibacterials category includes several subclasses of pharmaceutical APIs, such as nitroimidazoles, fusidanes, polymyxins, and glycopeptides. Each subclass comprises specific chemical compounds that target different types of bacteria through distinct mechanisms of action.
Nitroimidazoles are effective against anaerobic bacteria and protozoa by interfering with their DNA replication. They are commonly used in the treatment of infections in the gastrointestinal tract, pelvic area, and respiratory system. Fusidanes, on the other hand, inhibit bacterial protein synthesis and are particularly active against Gram-positive bacteria. They find application in treating skin and soft tissue infections caused by Staphylococcus aureus.
Polymyxins are cyclic peptides that disrupt the integrity of bacterial cell membranes, rendering them inactive. These APIs are potent against Gram-negative bacteria and are often reserved for multidrug-resistant strains.
Glycopeptides, such as vancomycin, are essential for combating Gram-positive bacterial infections, including methicillin-resistant Staphylococcus aureus (MRSA). They inhibit bacterial cell wall synthesis, leading to bacterial death.
The Other antibacterials category plays a critical role in providing effective treatment options for bacterial infections, particularly when other classes of antibacterials have shown limited efficacy. Pharmaceutical companies continually explore and develop new compounds within this category to address emerging antibiotic resistance and enhance patient care.
Acetohydroxamic Acid API manufacturers & distributors
Compare qualified Acetohydroxamic Acid API suppliers worldwide. We currently have 2 companies offering Acetohydroxamic Acid API, with manufacturing taking place in 1 different countries. Use the table below to review supplier type, countries of origin, certifications, product portfolio and GMP audit availability.
| Supplier | Type | Country | Product origin | Certifications | Portfolio |
|---|---|---|---|---|---|
| Isochem | Producer | France | France | CoA, USDMF | 12 products |
| PMC Isochem | Producer | France | France | CoA, GMP | 7 products |
When sending a request, specify which Acetohydroxamic Acid API quality you need: for example EP (Ph. Eur.), USP, JP, BP, or another pharmacopoeial standard, as well as the required grade (base, salt, micronised, specific purity, etc.).
Use the list above to find high-quality Acetohydroxamic Acid API suppliers. For example, you can select GMP, FDA or ISO certified suppliers. Visit our help page to learn more about sourcing APIs via Pharmaoffer.
