Carbenicillin
- Atc Codes:J01CA03
- CAS Codes:26605-69-6#35531-88-5
- PHARMGKB ID:26605-69-6#35531-88-5
Table of contents
- Brand Names
- Chemistry
- Pharmacologic Category
- Mechanism of Action
- Therapeutic Use
- Unlabeled Use
- Pregnancy and Lactation Implications
- Contraindications
- Warnings and Precautions
- Adverse Reactions
- Inhibits
- Drug Interactions
- Dosage
- Pharmacokinetics and Pharmacodynamics
- Special Considerations
Brand Names
Europe
Poland: Carbenicillin.
North America
USA: Geocillin (d).
Drug combinations
Chemistry
Carbenicillin Indanyl Sodium: C~26~H~25~N~2~NaO~6~S. Mw: 516.54. (1) 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[3-[(2,3-dihydro-1H-inden-5-yl)oxy]-1,3-dioxo-2-phenylpropyl]amino]-3,3-dimethyl-7-oxo-, monosodium salt, [2S-(2α,5α,6β)]-; (2) 1-(5-Indanyl)(2S,5R,6R)-N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-2-phenylmalonamate monosodium salt. CAS-26605-69-6; CAS-35531-88-5 (carbenicillin indanyl)(1972).
Pharmacologic Category
Antibacterials; Extended-spectrum Penicillins. (ATC-Code: J01CA03).
Mechanism of action
Inhibits bacterial cell wall synthesis by binding to the penicillin-binding proteins (PBPs) which in turn inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. Bacteria eventually lyse due to ongoing activity of cell wall autolytic enzymes (autolysins and murein hydrolases) while cell wall assembly is arrested.
Therapeutic use
Treatment of urinary tract infections, asymptomatic bacteriuria, or prostatitis caused by susceptible strains of enterococci, Enterobacter, Escherichia coli, Morganella morganii, Proteus mirabilis, P. vulgaris, P. rettgeri, or Pseudomonas aeruginosa. Most clinicians state that the drug is not a drug of choice for these infections.
Pregnancy and lactiation implications
Adverse events have not been observed in animal studies. Penicillins cross the placenta. Adequate studies with carbenicillin have not been completed in pregnant women. Use with caution during lactation.
Unlabeled use
Prophylaxis in patients undergoing transrectal biopsy of the prostate.
Contraindications
Hypersensitivity to carbenicillin, penicillins, or any component of the formulation.
Warnings and precautions
Serious and occasionally severe or fatal hypersensitivity (anaphylactoid) reactions reported in patients on penicillin therapy, especially with history of β-lactam hypersensitivity, history of sensitivity to multiple allergens, or previous IgE-mediated reactions (e.g. anaphylaxis, angioedema, urticaria). Use with caution in asthmatic patients. Prolonged use may result in fungal or bacterial superinfection, including C. difficile-associated diarrhea and pseudomembranous colitis. Use with caution in hepatic or renal impairment (avoid use if CrCl <10 mL/minute). Some penicillin derivatives may accelerate the degradation of aminoglycosides. Penicillins may cause apprehension, illusions, agitation, insomnia, depersonalization, and encephalopathy. Leukopenia and neutropenia reported. Oral carbenicillin should be limited to treatment of urinary tract infections.