Carbenicillin is a semi-synthetic penicillin antibiotic that is broad spectrum and active against both gram-positive and gram-negative bacteria including Pseudomonas. It works by inhibiting the final stage of bacterial cell wall synthesis. Common side effects include gastrointestinal issues like nausea and diarrhea. It is indicated for the treatment of urinary tract infections caused by susceptible bacteria. Dosing varies based on the infection being treated and a patient's kidney function.

1. MEDICINAL CHEMISTRY
COURSE INCHARGE : MISS WAJIHA
TOPIC: CARBENICILLIN
Group: 09

2. CARBENICILLIN
Carbenicillin is a semi-synthetic derivative of penicillin,
active as a broad spectrum antibiotic. Carbenicillin
belongs to the penicillin group of beta-lactam antibiotics.
Carbenicillin disrupts bacterial cell wall synthesis by
disrupting peptidoglycan cross-linking. Antimicrobial
spectrum includes Gram-positive, Gram-negative
bacteria and Pseudomonas.

3. Description
Kingdom:
Organic
Compounds
Chemical
Formula:
Molecular
mass: 378.401
g/mol
Storage
conditions: 2
to 8°C
Shipping
conditions:
Shipped on Dry
Ice or Blue Ice.
Shelf life: 24
months from
date of
manufacture
Solubility: H2O:
soluble50
mg/mL
Assay : 89.0-
100.5%
anhydrous
basis

4. MECHANISM OF ACTION
Free carbenicillin is the predominant
pharmacologically active fraction of the salt.
Carbenicillin exerts its antibacterial
activity by interference with final cell
wall synthesis of susceptible bacteria.
Penicillins acylate the penicillin-sensitive
transpeptidase C-terminal
domain by opening the lactam ring.
This inactivation of the enzyme
prevents the formation of a cross-link
of two linear peptidoglycan strands,
inhibiting the third and last stage of
bacterial cell wall synthesis.
Cell lysis is then mediated by bacterial
cell wall autolytic enzymes such as
autolysins; it is possible that carbenicillin
interferes with an autolysin inhibitor.

5. PHARMCOKINETICS
Absorption:
Rapidly absorbed
from the small
intestine
following oral
administration.
Protein binding:
30 to 60%
Metabolism:
extensively
metabolized
Oral
bioavailability is
30 to 40%.
Half life 1 hour

6. PHARMACODYNAMICS
Carbenicillin is a semisynthetic penicillin. Though
carbenicillin provides substantial in vitro activity against a
variety of both gram-positive and gram-negative
microorganisms, the most important aspect of its profile is
in its antipseudomonal and antiproteal activity. Because of
the high urine levels obtained following administration,
carbenicillin has demonstrated clinical efficacy in urinary
infections due to susceptible strains of: Escherichia
coli, Proteus mirabilis, Proteus vulgaris,Morganella
morganii, Pseudomonas species, Providencia
rettgeri, Enterobacter species, and Enterococci (S. faecalis).

14. INDICATION
it is indicated in the treatment of acute and chronic infections of
the upper and lower urinary tract and in asymptomatic bacteriuria
due to susceptible strains of the following organisms:
Escherichia coli
Proteus mirabilis
Morganella morganii (formerly Proteus morganii)
Providencia rettgeri (formerly Proteus rettgeri)
Proteus vulgaris
Pseudomonas
Enterobacter
Enterococci

15. ADVERSE EVENTS
Gastrointestinal
The most frequent
adverse reactions
associated with
Carbenicillin therapy
are related to the
gastrointestinal tract.
Nausea, bad taste,
diarrhea, vomiting,
flatulence, and
glossitis were
reported. Abdominal
cramps, dry mouth,
furry tongue, rectal
bleeding, anorexia,
and unspecified
epigastric distress
were rarely reported.
Dermatologic
Hypersensitivity
reactions such as skin
rash, urticaria, and
less frequently
pruritus.
Hematologic
As with other
penicillins, anemia,
thrombocytopenia,
leukopenia,
neutropenia, and
eosinophilia have
infrequently been
observed. The clinical
significance of these
abnormalities is not
known.
Miscellaneous
Other reactions
rarely reported were
hyperthermia,
headache, itchy eyes,
vaginitis, and loose
stools.
Abnormalities of
Hepatic
Function Tests
Mild SGOT elevations
have been observed
following
Carbenicillin
administration.

16. CONTRA-INDICATION
Carbenicillin is
ordinarily
contraindicated
in patients who
have a known
penicillin
allergy.
INTERACTION
Carbenicillin’s
blood levels may
be increased and
prolonged by
concurrent
administration
of probenecid.

17. CHILDREN DOSE
• When it is used parenterally for urinary tract infection in children,
the usual dose is 50-200mg/kg per day given every 4 hours.
• For severe infections of UTI, the dose can be increased to 400-
500mg/kg per day.
• The oral form is not predictably effective in children.
ADULT DOSE
• Usual Adult Dose for Cystitis: 382 to 764 mg orally 4 times a day for
3 to 7 days (Escherichia coli, Proteus, or Enterobacter as causative
agent). 764 mg orally 4 times a day for 3 to 7 days (Pseudomonas or
Enterococcus as causative agent).
• Usual Adult Dose for Prostatitis: 764 mg orally 4 times a day for 14
days. Chronic prostatitis may require 1 to 3 months of antimicrobial
therapy.
RENAL DOSE
ADJUSTMENTS
CrCl 10 to 50
mL/min: 382 to
764 mg orally
every 12 to 24
hours.
CrCl<10 mL/min:
Use not
recommended
because of
inadequate
urinary
concentrations.