Mezlocillin is a broad-spectrum penicillin antibiotic. It has the chemical formula D-a (2-oxo-3-mesyl-imidazolidinyl)-carbonyl amino-benzyl-penicillin. It is an ureido-penicillin and resembles an a-amino-substituted ampicillin [1-2]]. Mezlocillin alone is available for clinical use as Mezlint. It is now rarely used clinically, but has been replaced in a small number of regions by a ﬁxed combination of mezlocillin and sulbactam, a b-lactamase inhibitor.It is active against both Gram-negative and some Gram-positive bacteria. Unlike most other extended spectrum penicillins, it is excreted by the liver, therefore it is useful for biliary tract infections, such as ascending colangitis.
This drug has no special advantages for the treatment of P. aeruginosa infections, but it has been used with success for the treatment of moderate and severe infections caused by other sensitive Gram-negative aerobic and anaerobic bacilli [3-4]. Mezlocillin is quite effective in the treatment of septicemia, pneumonia, peritonitis, and infections of the urinary tract, skin and soft tissue, bone and joint, and the biliary tract caused by susceptible Gram-negative and Gram-positive aerobic and anaerobic bacteria [5-9]. Mezlocillin is inadequate if used as a single drug and without being combined with another agent, such as an aminoglycoside or sulbactam, in empiric therapy of granulocytopenic and other immunocompromised patients with fever [10-11]. If it is combined with an aminoglycoside, such as gentamicin or netilmicin, it is more effective, but results are similar to those obtained with ticarcillin plus an aminoglycoside [12-14].
Mezlocillin, as a single preoperative dose of 5 g or three mezlocillin doses 8-hourly, has been tried as prophylaxis of wound infection after appendicectomy and biliary and colorectal surgery. Some authors have found that mezlocillin alone is as good as cefuroxime plus metronidazole for the prevention of wound infection after large bowel surgery [15-16]. Although these two regimens were found equally satisfactory following appendicectomy and biliary and gastroeosophageal surgery, others found that in patients undergoing colorectal surgery, mezlocillin was inferior (wound infection rate, 30.2%) to cefuroxime–metronidazole (wound infection rate, 11.5%) .
An infant with Flavobacterium meningosepticum meningitis and
ventriculitis was cured by a synergistic combination of mezlocillin and
cefoxitin, when previous therapy with erythromycin and rifampicin had failed
. In vitro and in vivo antagonism between mezlocillin and
cefoxitin can occur with some Gram-negative bacilli. Data from in vitro
studies and animal experiments suggest that mezlocillin should be effective for
the treatment of Enterococcus faecalis infections, and a
mezlocillin–gentamicin combination may be effective for E. faecalis
endocarditis . Mezlocillin is unlikely to be superior to penicillin G or
ampicillin for this purpose. Animal experiments also indicate that mezlocillin
may be about as effective as ampicillin for the treatment of serious L.
monocytogenes infections, such as meningitis .
Dosage and Administration
The usual dosage for adults is 200–450 mg/kg body weight
per day, given i.m. or more commonly i.v., in six divided doses. Each dose can
For children, the normal dose is the same as for adults, i.e. 200–450 mg/kg body weight per day, with the optimal dosage for serious infections being 450 mg/kg/day, given i.v. in six divided doses . Similar to piperacillin, higher mezlocillin doses (usually double) are needed for patients with cystic ﬁbrosis . Recommended mezlocillin dosages for newborn infants [29-31]are as follows:
Preterm infants (gestational age less than 38 weeks) who are 7 days old or younger – 75 mg mezlocillin per kg body weight 12-hourly (150 mg/kg/day);
preterm infants older than 7 days or term infants 7 days old or younger – 75 mg mezlocillin per kg 8-hourly (225 mg/kg/day);
and for term infants older than 7 days, a dosage of 75 mg/kg 6-hourly (300 mg/kg/day) is appropriate.
Impaired renal function
Impaired hepatic function
In a study conducted on 1148 mezlocillin-treated patients for adverse reactions, hypersensitivity, manifested by drug fever, skin rashes, or eosinophilia, occurred in 0.3%, 1.8%, and 2.2% of treated patients, respectively .
High doses of mezlocillin given i.v., similar to ‘‘massive’’ doses of penicillin G or carbenicillin, may have the propensity to cause neurotoxicity .
Similar to carbenicillin and ticarcillin, mezlocillin, azlocillin, piperacillin, and apalcillin can cause a disturbance of platelet function [41-42].
Neutropenia and thrombocytopenia
As with carbenicillin and ticarcillin and other b-lactam antibiotics, reversible neutropenia can occur during therapy with mezlocillin, azlocillin, and piperacillin [25, 43-44]. This side-effect is more common with these penicillins than with carbenicillin. Thrombocytopenia can also rarely occur [45-47].
Reversible hepatotoxicity, mainly
manifested by elevated enzymes, such as serum alkaline phosphatase, SGOT, and
SGPT, has been noted
Some patients have developed nausea and diarrhea associated with parenteral use of this drug. A positive Coombs’ test has developed in a few patients treated by either mezlocillin or piperacillin, but hemolytic anemia has not been observed. Renal function deteriorated in two patients during mezlocillin therapy, but this reverted to normal when the drug was ceased [39, 44]. Surprisingly, in one study, side-effects characteristic of gentamicin, such as nephrotoxicity and ototoxicity, were more common when gentamicin was combined with mezlocillin than with a gentamicin-ticarcillin combination; these regimens were used to treat febrile episodes in neutropenic patients . By contrast, in a prospective randomized trial in which netilmicin was combined with either mezlocillin, piperacillin, ticarcillin, or cefoperazone, cases of nephro and ototoxicity were not correlated with any particular b-lactam . Two patients have been described who developed acute interstitial nephritis, and mezlocillin alone was implicated as the cause .
The half-life of mezlocillin varies
depending on the dose and is about 1 hour at a dose of 3 g and increases to
about 1.2 hours if the dose is 5 g . Renal clearance of the drug is also
somewhat reduced when larger doses are used, at least in the case of mezlocillin
The drug is not orally available.
After i.v. administration of a 3-g dose of mezlocillin given over a 15minute period, the mean Cmax at the end of the infusion is 269 mg/ml. Thereafter, the serum level falls, and at 6 hours it is less than 10 mg/ml. Its half-life (66 minutes) is similar to that of ampicillin and carbenicillin. When 3 g of mezlocillin is given i.v. every 4 hours as a 2-hour infusion, the peak serum level just after the infusion is over 100 mg/ml, and levels are maintained above 50 mg/ml between infusions . If 1 g of mezlocillin is given as a ‘‘bolus’’ injection i.v. over 4–5 minutes to normal adults, serum levels are 56.2, 17.2, 2.9, and 0.1 mg/ml at 5 minutes, 30 minutes, 2 hours, and 6 hours, respectively. When a 5-g i.v. dose is administered in the same manner, serum levels are 383.5, 145.5, 26.9, 2.2, and 0.4 mg/ml at 5 minutes, 30 minutes, 2 hours, 6 hours, and 8 hours, respectively .
Mezlocillin levels were quite high in
pleural and ascitic ﬂuid , but mezlocillin and piperacillin penetrated poorly
into bronchial secretions, where concentrations of only 1–5
mg/ml were attained with usual doses [5, 55]. Mezlocillin, azlocillin,
and piperacillin penetrated well into interstitial and wound ﬂuids, but after
usual doses only low levels were reached in normal bone . Mezlocillin also
In ten patients after cholecystectomy with a T-tube in situ, i.m. injection of 1 g of mezlocillin resulted in a mean biliary peak concentration of 295.7 mg/ml .
Mezlocillin, azlocillin, and
piperacillin are excreted unchanged in the urine by both glomerular ﬁltration
and tubular secretion. Approximately
Signiﬁcant amounts of mezlocillin, azlocillin, piperacillin, and apalcillin are eliminated via the bile. The percentage of these drugs eliminated via bile may increase in patients with impaired hepatic function; this is probably because there is less biotransformation in the liver . The proportion of an administered dose which is eliminated via the bile varies considerably from patient to patient. In a clinical study, biliary elimination of mezlocillin ranged from 26.65% to 0.05% of the administered dose, and this did not correlate with renal function . Biliary concentrations and clearance of mezlocillin were low in patients with cholelithiasis. In patients with T-tube drainage following cholecystectomy, after i.v. doses of 2 and 4 g, 22.1% and 14.2% of the administered doses, respectively, were excreted in the bile. These ﬁndings suggest a capacity-limited, dose-dependent process of biliary excretion.
Mechanism of Action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Piperacillin inhibits 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 Piperacillin interferes with an autolysin inhibitor.
The antibacterial spectra of ureidopenicillins are similar to those of carbenicillin and ticarcillin, but there are differences between their degree of activity against various bacterial species. All of these antibiotics have lost much of their activity owing to emergence of resistance. To some extent, that problem has been reduced for mezlocillin and piperacillin, which are available in ﬁxed combinations with sulbactam and tazobactam, respectively. The comparative in vitro susceptibility data for these agents against common pathogens are shown in Table 1.
Table 1. In vitro susceptibility of common pathogens to mezlocillin, azlocillin, piperacillin, and apalcillin in comparison with ticarcillin.
Mezlocillin is more active than carbenicillin and ticarcillin against most Eschericia coli, Enterobacter spp., Proteus vulgaris, P. rettgeri,and Morganella morganii strains. It is also more active than ticarcillin against Klebsiella spp.; when introduced, mezlocillin inhibited more than 50% of strains at clinically achievable concentrations [2, 61]. Activity of mezlocillin was about the same as that of ticarcillin against Serratia marcescens and P. aeruginosa . As with azlocillin, the activity of mezlocillin against P. aeruginosa was markedly inoculum dependent and MBCs are much higher than MICs, suggesting that each culture contains some highly mezlocillin-resistant P. aeruginosa strains [1, 63-64]. Providencia alkalifaciens is quite sensitive (MIC 1–2 mg/ml), but P. stuartii is relatively mezlocillin resistant . Most strains of Pseudomonas spp. other than P. aeruginosa,such as Burkholderia cepacia, were inhibited by lower mezlocillin than carbenicillin concentrations. Mezlocillin and carbenicillin were equally active against Acinetobacter spp. . Salmonellae and shigellae were mezlocillin sensitive; ampicillin-resistant strains of both species were mezlocillin resistant [4, 67]. Mezlocillin and piperacillin maintained some activity against amoxillin-resistant strains of Helicobacter pylori 68], but this has questionable clinical relevance. Prevotella melaninogenica was quite sensitive, whilst B. fragilis was variably susceptible. Activity of mezlocillin against B. fragilis was similar to that of penicillin G, ampicillin, and carbenicillin) . As mezlocillin is vulnerable to many beta-lactamases of Gram-negative bacteria, many isolates, especially hospital-associated strains of these bacteria may be highly mezlocillin resistant [3, 70]. Mezlocillin and other acylamino penicillin derivatives are not resistant to TEM b-lactamases, which are the most frequent plasmid mediated b-lactamases among resistant Enterobacteriaceae . However, some E. coli isolates which produce TEM-1 b-lactamase remain relatively mezlocillin sensitive, whereas they are resistant to ampicillin . Mezlocillin is active against Haemophilus inﬂuenzae, its activity exceeding that of ampicillin . Meningococci and gonococci are quite sensitive. Strains of Neisseria gonorrhoeae highly susceptible to penicillin G are equally sensitive to mezlocillin. Strains with intermediate susceptibility to penicillin G (MICs 0.125–0.5 mg/ml) are much more sensitive to mezlocillin (MICs 0.0004–0.125 mg/ml). The same applies to gonococcal strains with even higher intrinsic resistance to penicillin G; for those with penicillin G MICs of 1–4 mg/ml, mezlocillin MICs are 0.06–0.5 mg/ml (. b-lactamase-producing gonococci are mezlocillin resistant. Mezlocillin is highly active against Gram-positive bacteria, such as Streptococcus pyogenes, group B streptococci, S. pneumoniae,and S. viridans, but penicillin G and ampicillin are more active against these organisms. Mezlocillin is slightly less active than ampicillin, but equally active as penicillin G against Enterococcus faecalis . Some authors have found that mezlocillin, unlike penicillin G and ampicillin, has identical MICs and MBCs against this organism . Listeria monocytogenes is also mezlocillin sensitive . It is moderately active against penicillin G-sensitive staphylococci, but b-lactamase-producing strains are resistant . Similar to most other penicillins, mezlocillin is inactive against Chlamydia trachomatis .
In vitro synergy and antagonism
In combination with an aminoglycoside (such as gentamicin, tobramycin, amikacin, or netilmicin), ureidopenicillins act synergistically against many strains of Gram-negative bacilli, such as P. aeruginosa, E. coli, P. vulgaris, P. rettgeri, Morganella morganii, and Klebsiella, Citrobacter, Enterobacter, and Serratia spp.
In vitro synergy occurs with
mezlocillin-sensitive and -resistant strains of these bacteria [76, 78-82].
Mezlocillin (and related penicillins), combined with some b-lactamase
resistant ephalosporins, may be antagonistic against certain Gram-negative
bacilli. When a mezlocillin–cefoxitin combination was tested against B.
fragilis, synergism was observed in 10/20 strains, but there was no
antagonism (Bansal and Thadepalli, 1983).
Other pharmacological effects
CAS number: 51481-65-3 EINECS:
Molecular Formula: C21H25N5O8S2
Average mass: 539.581909 Da
Monoisotopic mass: 539.114441 Da
Systematic name: 2S,5R,6R)-3,3-dimethyl-6-[[(2R)-2-[(3-methylsulfonyl-2-oxo-imidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Std. InChI: 1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12?,13-,14+,17-/m1/s1
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