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Carbenicillin
Carbenicillin
Carbenicillin
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Carbenicillin
Clinical data
Trade namesGeocillin; Pyopen
Other namesCB[1]
AHFS/Drugs.comMonograph
Pregnancy
category
Routes of
administration		Oral, parenteral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30 to 40%
Protein binding30 to 60%
MetabolismMinimal
Elimination half-life1 hour
ExcretionRenal (30 to 40%)
Identifiers
  • (2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-
    3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]
    heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.022.882 Edit this at Wikidata
Chemical and physical data
FormulaC17H18N2O6S
Molar mass378.40 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)O)[C@H]3SC2(C)C
  • InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1 checkY
  • Key:FPPNZSSZRUTDAP-UWFZAAFLSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins.[2] It was discovered by scientists at Beecham and marketed as Pyopen. It has Gram-negative coverage which includes Pseudomonas aeruginosa but limited Gram-positive coverage. The carboxypenicillins are susceptible to degradation by beta-lactamase enzymes, although they are more resistant than ampicillin to degradation. Carbenicillin is also more stable at lower pH than ampicillin.

Pharmacology

[edit]

The antibiotic is highly soluble in water and is acid-labile. A typical lab working concentration is 50 to 100 μg per mL.[citation needed]

It is a semi-synthetic analogue of the naturally occurring benzylpenicillin. Carbenicillin at high doses can cause bleeding. Use of carbenicillin can cause hypokalemia by promoting potassium loss at the distal convoluted tubule of the kidney.[citation needed]

In molecular biology, carbenicillin may be preferred as a selecting agent (see plasmid stabilisation technology) because its breakdown results in byproducts with a lower toxicity than analogous antibiotics like ampicillin. Carbenicillin is more stable than ampicillin and results in fewer satellite colonies on selection plates. However, in most situations this is not a significant problem so ampicillin is sometimes used due to its lower cost.[citation needed]

Spectrum of bacterial susceptibility and resistance

[edit]

Carbenicillin has been shown to be effective against bacteria responsible for causing urinary tract infections including Pseudomonas aeruginosa, Escherichia coli, and some Proteus species. The following represents carbenicillin susceptibility data for a few medically significant organisms.[3] This is not representative of all species of bacteria susceptible to carbenicillin exposure.

  • Escherichia coli 1.56 μg/ml - 64 μg/ml
  • Proteus mirabilis 1.56 μg/ml - 3.13 μg/ml
  • Pseudomonas aeruginosa 3.13 μg/ml - >1024 μg/ml

References

[edit]

Further reading

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Carbenicillin

View on Grokipedia
from Grokipedia
Carbenicillin is a semisynthetic beta-lactam antibiotic belonging to the carboxypenicillin class of penicillins, characterized by its molecular formula C₁₇H₁₈N₂O₆S and a 6β-(2-carboxy-2-phenylacetamido) side chain that distinguishes it from earlier penicillins. It functions as a bactericidal agent by binding to penicillin-binding proteins, thereby inhibiting the final stage of bacterial cell wall synthesis and leading to cell lysis, particularly in Gram-negative bacteria. Developed in the late 1960s, carbenicillin was the first penicillin with significant activity against , addressing a critical gap in treating infections from this opportunistic pathogen that was increasingly problematic in hospital settings. Its introduction marked a milestone in broad-spectrum antibiotics, expanding the utility of penicillins beyond Gram-positive organisms to include many Gram-negative enteric bacteria such as , species, and some anaerobes. The parenteral form (carbenicillin disodium) was approved for intravenous use, while the oral carbenicillin indanyl sodium (marketed as Geocillin) was approved in 1972 for better gastrointestinal absorption, though it required higher doses due to variable bioavailability. Clinically, carbenicillin was primarily indicated for acute and chronic urinary tract infections, , and severe systemic infections caused by susceptible strains, often administered in with other agents to broaden coverage or overcome resistance. However, its limitations included instability against enzymes produced by resistant bacteria and lower potency compared to subsequent antipseudomonal penicillins like ticarcillin and piperacillin, which led to its gradual replacement. By the early , the oral formulation was discontinued in the United States due to the availability of more effective alternatives, though the compound remains used in laboratory settings for bacterial selection in . Contraindicated in patients with penicillin , carbenicillin's legacy underscores the evolution of toward broader and more stable agents.

History and Development

Discovery

Carbenicillin was discovered by scientists at Beecham Research Laboratories in the early 1960s as part of broader efforts to develop semi-synthetic penicillins with enhanced efficacy against Gram-negative bacteria, building on the 1957 isolation of 6-aminopenicillanic acid (6-APA) that enabled side-chain modifications to the penicillin core. Researchers, including Edward George Brain and John Herbert Charles Nayler, focused on derivatives that could address limitations of earlier penicillins like ampicillin, which showed only modest activity against challenging pathogens such as Pseudomonas aeruginosa. The initial synthesis of carbenicillin, chemically known as α-carboxybenzylpenicillin, occurred through of with a reactive of phenylmalonic , incorporating a carboxyphenyl to improve stability and penetration against Gram-negative organisms. This semi-synthetic approach modified the benzyl of (penicillin G) to confer the desired spectrum. The first reported synthesis was detailed in a 1965 British patent filed in , marking a pivotal advancement in antipseudomonal . Early preclinical studies rapidly demonstrated carbenicillin's superior antibacterial activity against compared to prior penicillins, including , with minimum inhibitory concentrations often 4- to 16-fold lower in vitro. For instance, a 1967 investigation reported that carbenicillin inhibited 90% of P. aeruginosa strains at concentrations of 50-100 μg/mL, significantly outperforming 's higher thresholds of 200-500 μg/mL, while retaining activity against other Gram-negatives like Proteus and . These findings, from laboratory assays on clinical isolates, underscored carbenicillin's potential as the first penicillin with clinically viable antipseudomonal effects, paving the way for subsequent clinical evaluation by Beecham.

Market Introduction and Current Status

Carbenicillin was commercialized in the late 1960s by Beecham Research Laboratories, initially as the injectable disodium salt under the brand name Pyopen for treating severe bacterial infections. The U.S. Food and Drug Administration (FDA) approved the injectable form in 1970 specifically for urinary tract infections caused by susceptible gram-negative bacteria. In 1972, the FDA approved the oral indanyl sodium ester formulation, marketed as Geocillin, expanding accessibility for outpatient treatment of urinary tract infections. During the 1970s and 1980s, carbenicillin reached peak clinical usage, particularly for infections caused by , where it was often combined with aminoglycosides for enhanced efficacy against this challenging pathogen. However, by the late 1980s, its role diminished as broader-spectrum carboxypenicillins like piperacillin, which demonstrated superior activity against species, became preferred alternatives. As of 2025, carbenicillin has been largely discontinued for human clinical use in major markets, including the , due to widespread bacterial resistance and the availability of more effective antibiotics; the oral Geocillin was withdrawn by its manufacturer in . It remains available primarily for applications, such as plasmid selection in research, with small-scale production ongoing to support these non-clinical needs. Beecham's original portfolio, including carbenicillin, was integrated into SmithKline Beecham following its 1989 merger with SmithKline Beckman, and further consolidated under GlaxoSmithKline after the 2000 acquisition of SmithKline Beecham by Glaxo , which streamlined global distribution but eventually contributed to the phase-out of older antibiotics like carbenicillin in favor of newer innovations.

Chemical Structure and Properties

Molecular Formula and Structure

Carbenicillin, in its free acid form, has the molecular formula C₁₇H₁₈N₂O₆S, while the disodium salt, which is the predominant pharmaceutical form, possesses the formula C₁₇H₁₆N₂Na₂O₆S. The core structure of carbenicillin consists of a β-lactam ring fused to a thiazolidine ring, forming the characteristic penam nucleus central to all penicillins. At the 6-position of this nucleus, a 6β-(2-carboxy-2-phenylacetamido) side chain is attached via an amide bond, which defines its classification as a carboxypenicillin. The full systematic IUPAC name is (2S,5R,6R)-6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. This side chain features a phenyl group and an α-carboxylic acid substituent on the acetyl moiety, distinguishing it from narrower-spectrum penicillins. The standard 2D structural diagram illustrates the bicyclic system, with the five-membered thiazolidine ring bearing a carboxylic acid at position 2 and two methyl groups at position 3, alongside the strained four-membered β-lactam ring bearing the amide side chain at position 6. In terms of , carbenicillin maintains the specific configurations at key chiral centers in the nucleus: 2S at the thiazolidine carboxylic acid-bearing carbon, 5R at the fusion point, and 6R at the attachment site, ensuring the β-orientation of the essential for . Compared to the parent penicillin G, which features a simple phenylacetamido (–NH–C(O)–CH₂–Ph), carbenicillin's addition of a carboxy group at the α-position of the (–NH–C(O)–CH(Ph)(COOH)) imparts enhanced acid stability and broadened activity against .

Physical and Chemical Characteristics

Carbenicillin appears as a white to off-white crystalline in its free form, while the disodium salt is typically a white to pale yellow . The compound exhibits high solubility in , with the disodium salt dissolving up to 50 mg/mL, though it is less soluble in and poorly soluble in most organic solvents. It is acid-labile, degrading rapidly below 3 due to of the β-lactam ring, with a of less than 30 minutes at 2.0. Carbenicillin demonstrates stability in neutral to alkaline solutions (pH 5.5–8.0), where it remains effective for extended periods under refrigerated storage, but it is unstable to heat and exhibits strong hygroscopicity, requiring desiccated conditions at -20°C for long-term preservation. The free has a molecular weight of 378.40 g/mol, while the disodium salt is 422.36 g/mol. Its pKa values include approximately 2.22 for one group and 3.25 for the other, influencing its ionization and in physiological conditions. Carbenicillin is more resistant to β-lactamase hydrolysis than but remains susceptible to degradation by these enzymes. Common formulations include the disodium salt for intravenous or , providing high aqueous for parenteral administration, and the indanyl sodium for oral use to enhance gastrointestinal absorption.

Medical and Laboratory Applications

Therapeutic Indications

Carbenicillin, a semisynthetic , was primarily indicated for the treatment of acute and chronic infections of the upper and lower urinary tract, , and asymptomatic bacteriuria caused by susceptible such as , , and . However, carbenicillin has been discontinued for medical use in the United States since 2008 due to the availability of more effective alternatives. Secondary indications included systemic infections such as septicemia, lower infections, and infections, and and infections when caused by sensitive organisms, particularly Pseudomonas species. In the 1970s, carbenicillin was particularly preferred for managing infections in immunocompromised patients, often in combination with gentamicin to enhance efficacy against severe cases like those in granulocytopenic individuals. Contraindications include to penicillins, and caution is advised in patients with renal impairment due to reduced excretion and potential accumulation. Clinical trials demonstrated efficacy in urinary tract infections caused by susceptible strains, with bacteriologic cure rates ranging from 70% to 90% in uncomplicated cases, though rates varied based on infection severity and organism sensitivity. For Pseudomonas infections, response rates reached up to 91% in treated cases.

Dosage and Administration

Carbenicillin was available in parenteral forms (disodium salt) for intravenous (IV) or administration and in oral form as carbenicillin indanyl sodium (Geocillin) for less severe infections, but both forms were discontinued in 2008 and are no longer available for medical use. For adults with uncomplicated urinary tract infections (UTIs), the recommended oral dose was 382–764 mg (1–2 tablets) every 6 hours for 3–7 days. For more serious UTIs or , the oral dose was 764 mg every 6 hours for 14 days, with chronic prostatitis potentially requiring 1–3 months of therapy. Parenteral administration was preferred for severe infections; typical adult doses included 1–2 g IV or every 6 hours for UTIs, escalating to 15–30 g/day IV in divided doses every 4–6 hours for life-threatening conditions such as septicemia. Treatment duration generally ranged from 7–14 days for UTIs, extending longer for complicated or systemic infections based on clinical response. In pediatric patients, the IV dose was 50–200 mg/kg/day divided every 4–6 hours, with adjustments for age, weight, and severity; maximum daily doses should not exceed equivalents. Oral use in children was limited due to insufficient data on safety and efficacy. Dosage adjustments were necessary in renal impairment to prevent accumulation, as carbenicillin is primarily excreted by the kidneys. The following table outlines recommended IV dosing for adults (70 kg) based on creatinine clearance (CrCl):
CrCl (mL/min)Dose (g) / Interval (hours)
>501–2 / 4–6
10–501–2 / 6–12
<101 / 12 (or avoid if possible)
Serum levels should be monitored in patients with renal dysfunction, particularly those receiving high doses. IV infusions should be administered over 30–60 minutes to minimize vein irritation and phlebitis; direct IV push was not recommended. Oral tablets were best taken on an empty stomach for optimal absorption, though they may be given with food if gastrointestinal upset occurs. The full course of therapy must be completed to reduce the risk of resistance development.

Use in Molecular Biology

In molecular biology, carbenicillin serves primarily as a selective agent for identifying and maintaining bacterial transformants that carry plasmids conferring ampicillin resistance, particularly in Escherichia coli strains. This application leverages its compatibility with β-lactamase-producing genes (such as bla or ampR) commonly found in cloning vectors, allowing researchers to isolate successfully transformed cells on selective media. Typical protocols involve incorporating carbenicillin into Luria-Bertani (LB) agar plates or broth at concentrations of 50–100 μg/mL to support plasmid propagation during routine cloning experiments. Compared to ampicillin, carbenicillin offers enhanced stability in culture media, reducing degradation by β-lactamases secreted from nearby resistant "satellite" colonies and minimizing the formation of such colonies that can complicate selection. This stability results in fewer toxic byproducts and more reliable selection outcomes, making it preferable for long-term plasmid maintenance and high-throughput screening. Its chemical properties contribute to sustained activity in agar plates stored at 4°C for several weeks, unlike ampicillin which breaks down more readily. Beyond bacterial cloning, carbenicillin is widely used in plant tissue culture protocols involving Agrobacterium-mediated transformation, where it eliminates residual cells post-co-cultivation without excessively harming explants. Concentrations of 250–500 mg/L are commonly added to selection media to suppress bacterial overgrowth while allowing transformed plant cells to regenerate. For laboratory preparation, carbenicillin is available as a disodium salt powder from suppliers like , which is filter-sterilized and added to autoclaved media to ensure sterility and potency.

Pharmacology

Mechanism of Action

Carbenicillin, a semisynthetic beta-lactam antibiotic, acts bactericidally by binding to penicillin-binding proteins (PBPs) in the cytoplasmic membranes of susceptible bacteria, such as PBP-3. These PBPs function as transpeptidases that catalyze the cross-linking of peptidoglycan strands during the final stage of bacterial cell wall synthesis. By acylating the active site serine residue of these enzymes through its beta-lactam ring, carbenicillin irreversibly inhibits their activity, preventing the formation of the rigid peptidoglycan layer essential for maintaining bacterial integrity. This disruption weakens the cell wall, activating autolytic enzymes and leading to osmotic lysis, particularly in actively dividing bacteria where peptidoglycan synthesis is most active. The bactericidal effect is time-dependent, requiring sustained inhibition during bacterial replication to achieve maximal efficacy. Carbenicillin's spectrum favors Gram-negative bacteria due to its alpha-carboxy side chain, which imparts a di-anionic charge at physiological pH, facilitating passive diffusion through outer membrane porins in Gram-negative bacteria. This structural feature enhances penetration compared to less polar penicillins, enabling activity against organisms like Pseudomonas aeruginosa and Proteus species. While carbenicillin is susceptible to hydrolysis by certain beta-lactamases, it demonstrates greater stability than narrow-spectrum penicillins like , attributed to steric hindrance from the bulky 2-carboxy-2-phenylacetamido side chain that impedes enzyme access to the beta-lactam ring. As mammalian cells lack peptidoglycan and corresponding PBPs, carbenicillin exerts no direct cytotoxic effects on host tissues.

Pharmacokinetics

Carbenicillin is administered orally as the indanyl ester prodrug, which exhibits 30-40% bioavailability after rapid absorption from the small intestine, followed by hydrolysis to the active form in the body. Intravenous or intramuscular administration achieves complete and immediate bioavailability. The drug distributes widely with a volume of distribution of approximately 0.18 L/kg in adults. It achieves high concentrations in urine (e.g., 800 to 5500 μg/mL in newborns after high doses), making it suitable for . Penetration into cerebrospinal fluid is generally poor, with CSF/serum ratios around 10-15% even in the presence of meningeal inflammation. Plasma protein binding ranges from 30% to 60%. Metabolism of carbenicillin is minimal in the liver, with the parent compound primarily excreted unchanged. Excretion occurs mainly via the kidneys through both glomerular filtration and tubular secretion, with 80-99% of an intravenous dose recovered unchanged in the urine within 24 hours. The elimination half-life is approximately 1 hour in individuals with normal renal function but prolongs significantly to 10-20 hours in anuria or severe renal failure. For therapeutic efficacy, particularly against susceptible pathogens like Pseudomonas, peak serum levels of 200-400 μg/mL are typically achieved and targeted following high-dose intravenous administration.

Spectrum of Activity and Resistance

Susceptible Organisms

Carbenicillin exhibits a broad spectrum of antibacterial activity, primarily targeting gram-negative aerobic bacteria, with notable efficacy against certain pathogens responsible for urinary tract infections and systemic infections. Key susceptible gram-negative aerobes include Pseudomonas aeruginosa, which is a primary target due to carbenicillin's enhanced penetration through the outer membrane enabled by its carboxyl group, Escherichia coli, Proteus mirabilis, Morganella morganii, and Providencia rettgeri. Variable susceptibility is observed among Klebsiella pneumoniae and other Enterobacteriaceae, where activity may be reduced in beta-lactamase-producing strains. In vitro studies demonstrate effective inhibition of these organisms at clinically achievable concentrations. For instance, minimum inhibitory concentration (MIC) ranges for carbenicillin include 0.78–12.5 μg/mL against E. coli, 1.56–3.4 μg/mL against P. mirabilis, and 12.5–>200 μg/mL against P. aeruginosa, reflecting strain variability but overall susceptibility in sensitive isolates. These data underscore carbenicillin's role in treating infections caused by and Pseudomonas species, particularly in urinary and systemic contexts, though it is not typically first-line therapy. Activity against is limited compared to other penicillins, with moderate effects on some streptococci but inferior performance against staphylococci and enterococci. species show susceptibility at lower MICs (e.g., ≤1.56 μg/mL for streptococci), but carbenicillin is rarely used for these due to more potent alternatives. Against anaerobes, activity is restricted; for example, only 67% of strains have an MIC ≤100 μg/mL, limiting its utility in anaerobic infections.
OrganismExample MIC Range (μg/mL)
Escherichia coli0.78–12.5
Proteus mirabilis1.56–3.4
Pseudomonas aeruginosa12.5–>200
Bacteroides fragilis≤100 (67% strains)
This table summarizes representative susceptibility data from clinical isolates, highlighting carbenicillin's targeted efficacy against gram-negative aerobes while noting limitations elsewhere.

Mechanisms of Bacterial Resistance

Bacterial resistance to carbenicillin primarily arises through enzymatic degradation, reduced drug accumulation, and alterations to the target site. Enzymatic mechanisms involve that hydrolyze the beta-lactam ring essential for carbenicillin's activity. In such as , the plasmid-mediated TEM-1 efficiently hydrolyzes carbenicillin, conferring high-level resistance. In , chromosomal AmpC (class C) degrades carbenicillin, with overproduction often resulting from mutations in regulatory genes like ampR or ampD. Metallo-, such as VIM and (class B), produced by P. aeruginosa isolates, also hydrolyze extended-spectrum penicillins like carbenicillin, though less efficiently than narrower-spectrum enzymes. Carbenicillin exhibits partial resistance to some compared to due to its bulky carboxylated , which sterically hinders enzyme access to the beta-lactam ring, reducing rates. Non-enzymatic mechanisms further contribute to resistance by limiting carbenicillin's intracellular accumulation. Reduced outer membrane permeability in , particularly P. aeruginosa, occurs via leading to loss or downregulation of porins like OprD or OprF, which decreases drug influx and elevates minimum inhibitory concentrations for penicillins. Efflux pumps, such as the MexAB-OprM system in P. aeruginosa, actively export carbenicillin from the periplasmic space, with overexpression driven by in repressors like mexR or nalD enhancing multidrug resistance. These mechanisms often combine with production to achieve synergistic resistance effects. Alterations to (PBPs) represent another key strategy, where bacteria modify the transpeptidase targets of carbenicillin. In P. aeruginosa, mutations in the ftsI encoding PBP3 reduce affinity for beta-lactams, including carbenicillin, allowing continued synthesis despite drug presence. Clinically, these resistance mechanisms have contributed to rising prevalence of resistant P. aeruginosa isolates, particularly in settings and among high-risk clones such as ST175 and ST244. However, due to its replacement by more effective agents, carbenicillin is rarely used clinically today, and contemporary resistance surveillance focuses on newer antipseudomonal beta-lactams. This trend complicates treatment of infections like and bacteremia, historically necessitating with aminoglycosides (e.g., gentamicin or tobramycin) to achieve and overcome efflux and permeability barriers. In laboratory settings, resistance via production manifests as satellite colonies during plasmid selection on carbenicillin-containing media. secretion from resistant colonies degrades nearby , permitting growth of sensitive satellite cells; however, carbenicillin's stability minimizes this compared to .

Adverse Effects

Common Side Effects

The most common side effects of carbenicillin are mild and primarily affect the , particularly with oral administration where they are dose-related. These include , , , abdominal cramps, and , with and a in the mouth also frequently reported. In controlled clinical studies involving 344 patients, gastrointestinal disturbances were the most prevalent adverse reactions associated with oral carbenicillin therapy. Overall, mild adverse effects occurred in approximately 23% of patients receiving high doses over prolonged periods, though most did not require discontinuation of treatment. Mild reactions, such as , pruritus, and urticaria, are also common and non-anaphylactic in nature. These dermatologic effects arise in 1-10% of individuals exposed to carboxypenicillins like carbenicillin. Other frequent side effects include and pain at the site. Management of gastrointestinal symptoms typically involves dose reduction if feasible, administration of antiemetics for and , or to mitigate by supporting balance.

Serious Adverse Effects

Serious adverse effects of carbenicillin, though infrequent, can be life-threatening and necessitate prompt medical intervention. reactions represent a primary concern, including , , and severe cutaneous manifestations such as Stevens-Johnson syndrome. These reactions arise due to with other beta-lactam antibiotics, with an incidence of severe estimated at less than 0.1% among exposed patients. Hematologic toxicities are particularly associated with high-dose regimens exceeding 30 g/day, often administered intravenously for severe infections. Carbenicillin inhibits platelet aggregation, leading to a bleeding diathesis characterized by prolonged bleeding time and increased risk of hemorrhage, even in patients with normal renal function. Additionally, hypokalemia may occur through interference with distal tubular potassium secretion, as carbenicillin acts as a nonreabsorbable anion that enhances renal potassium excretion. Hepatic effects, while typically mild, can include transient elevations in liver enzymes such as SGOT. Rare instances of , typically anicteric and reversible upon discontinuation of the drug, have been reported. Renal complications encompass allergic , an immune-mediated inflammation of the renal that can lead to . This risk underscores the need for careful monitoring in patients with pre-existing , where dosage adjustments are essential to prevent accumulation. Other serious effects include seizures, which may develop in patients with renal failure due to elevated serum levels of carbenicillin causing toxicity. difficile-associated (CDAD) has been reported with carbenicillin use, ranging from mild to fatal . During prolonged carbenicillin , especially at high doses, routine monitoring of (CBC), serum electrolytes, and renal function is recommended to detect these adverse effects early and guide management.

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