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. 

Therapeutic use

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%) [17].

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 [18]. 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 [19]. 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 [20].


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
be injected directly into the i.v. tubing, but it is preferable to give it as an infusion over 15–30 minutes. A common adult dosage for serious infections is 3 g i.v. 4-hourly or 4 g 6-hourly [5, 8, 21]. Alternatively, a dosage of 5 g every 8 hours is satisfactory [22-23]. Higher dosages, such as 5 g i.v. 6-hourly [4] or 10 g i.v. 8-hourly [24], have been used. Some authors have given adults doses as large as 36 g daily (600 mg/kg/day), usually in six divided doses [25], but this is unnecessary for infections, however severe, caused by sensitive microorganisms. For the treatment of uncomplicated urinary tract infections, smaller doses, such as 2 g every 8 hours, are sufficient [26]. Such doses may be conveniently administered by the i.m. route, with or without the addition of lidocaine [25].


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 [27]. Similar to piperacillin, higher mezlocillin doses (usually double) are needed for patients with cystic fibrosis [28]. 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

Patients with renal failure require only slight modification of mezlocillin dosage provided they have normal liver function and relatively low doses are used; under these conditions, the mean mezlocillin half-life in normal patients of 1.1 hours is prolonged to only 1.6 hours in patients with severe renal failure [32]. With low mezlocillin dosage (2 g 6- or 8-hourly), dose reduction is necessary only in severe renal failure (creatinine clearance <10 ml/min), when the dosage should be reduced only by approximately 30%. Some mezlocillin is removed by hemodialysis, so that during this procedure the same dosage regimen as for patients with normal renal function can be used. Very little of the drug is removed during peritoneal dialysis, so that reduced dosage is necessary [33-35]. Mezlocillin clearance by both renal and nonrenal mechanisms is dose dependent, and there is a marked decrease in the clearance of the drug by both mechanisms over a 1–5 g dose range [36]. According to these authors, large mezlocillin dosages (5 g 6-hourly) should be adjusted for all degrees of renal functional
impairment, by altering the intervals between the 5-g doses. Alternatively, the dosing interval may be left unchanged and individual doses reduced accordingly [37].

Impaired hepatic function

Mezlocillin dose should be reduced in patients with moderate or severe hepatobiliary dysfunction [38].


Hypersensitivity reactions

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 [39].


High doses of mezlocillin given i.v., similar to ‘‘massive’’ doses of penicillin G or carbenicillin, may have the propensity to cause neurotoxicity [40].

Bleeding disorders

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
in 0.9% of mezlocillin-treated patients [25]. One patient with severe cholestatic jaundice caused by mezlocillin has been reported [48].

Other side-effects

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 [49]. 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 [50]. Two patients have been described who developed acute interstitial nephritis, and mezlocillin alone was implicated as the cause [51].



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 [52]. Renal clearance of the drug is also somewhat reduced when larger doses are used, at least in the case of mezlocillin [36, 53].

Protein binding 16–59%
Hepatic (20–30%)
Half-life 1.0–1.2 hours
Cmax (mg/ml) 269
tmax (hrs)  
Distribution volume Vd  
Excretion Renal (50%) and biliary


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 [54]. 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 [52].

Mezlocillin levels were quite high in pleural and ascitic fluid [5], 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 [28]. Mezlocillin also penetrated
well into heart valves and papillary muscles [28] and into human prostatic tissue [56].

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 [57].


Mezlocillin, azlocillin, and piperacillin are excreted unchanged in the urine by both glomerular filtration and tubular secretion. Approximately
50–80% of an i.v. dose of these drugs is eliminated via the kidneys in an unchanged form [52, 58-59]. With dose increments, an increasing proportion of all these drugs is recovered unchanged in the urine. This is because with higher doses nonrenal mechanisms for drug elimination become saturated. Probenecid decreases renal excretion of these penicillins by partial blockage of renal tubular secretion. High concentrations of the active form of all these drugs are attained in the urine after usual i.m. or i.v. doses.

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 [28]. 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 [60]. 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.

Antibacterial activity

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.


MIC (mg/ml)

Ticarcillin Mezlocillin Azlocillin Piperacillin Apalcillin
Staphylococcus aureus, non penicillinase producer 1.25 0.2 0.2 0.78 0.39
Staphylococcus pyogenes 0.5 0.025 <0.1 0.1 0.1
Streptococcus pneumoniae 1.25 0.025 0.1 0.01 0.05
Enterococcus faecalis 125 1 0.5 0.4-1.6 12.5
Clostridium perfringens 0.5 0.07 0.04 0.06-4 1.56
Escherichia coli 5 1-2 1-8 0.8 0.39
Enterobacter spp. 5 2-8 12.5-100 1.6 3.1
Klebsiella spp. 500 12.5-100 12.5->100 3.1 6.3
Serratia marcescens 12.5 12.5 12.5 0.8->100 25
Proteus mirabilis 1.25 1.56 1.56 0.2 0.76
Proteus vulgaris 2.5 1.56 12.5 0.78 12.5
Morganella morganii 2.5 1.56 12.5 0.78 3.1
Salmonella typhi 2.5 2 8 0.39 3.1
Neisseria gonorrheae 0.02 0.005 0.005 0.015-0.03 0.1
Haemophilus influenzae 0.25 0.15-0.25 0.06 0.015-0.03 -
Pseudomonas aeruginosa 25 25-50 12.5 6.5 6.3
Prevotella melaninogenica 0.1-4 0.5-4 - - -
Bacteroides fragilis 4-128 1-128 1-128 25 25

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 [62]. 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 [65]. 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. [66]. 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) [69]. 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 [71]. However, some E. coli isolates which produce TEM-1 b-lactamase remain relatively mezlocillin sensitive, whereas they are resistant to ampicillin [72]. Mezlocillin is active against Haemophilus influenzae, its activity exceeding that of ampicillin [73]. 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 ([74]. 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 [75]. Some authors have found that mezlocillin, unlike penicillin G and ampicillin, has identical MICs and MBCs against this organism [76]. Listeria monocytogenes is also mezlocillin sensitive [20]. It is moderately active against penicillin G-sensitive staphylococci, but b-lactamase-producing strains are resistant [73]. Similar to most other penicillins, mezlocillin is inactive against Chlamydia trachomatis [77].

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).
In studies in which mezlocillin was combined with either cefoxitin,
cefotaxime, cefoperazone, or moxalactam, and tested against
Enterobacteriaceae and P. aeruginosa, the most common result was
indifference, but antagonism occurred occasionally with mezlocillin–
cefoxitin (Neu and Labthavikul, 1982b). The effects of combining
mezlocillin (or piperacillin) with cefoxitin, cefamandole, or cephalothin
were studied by Kuck et al. (1981). Against most Gramnegative
bacilli there was either synergy or indifference, but with
P. aeruginosa, P. vulgaris, P. rettgeri, Serratia, and Enterobacter spp.,
antagonism was commonly observed, particularly with combinations
containing cefoxitin. In animals infected with organisms showing this
in vitro antagonism, much higher doses of mezlocillin were required to
control infection when it was combined with a cephalosporin than
when it was used singly. Sanders et al. (1982) found that cefoxitin–
mezlocillin antagonism occurred with strains of Gram-negative bacilli
which possessed inducible beta-lactamases. These chromosomally
mediated enzymes are present in many Gram-negative bacteria, such
as Enterobacter, Serratia, and Pseudomonas spp. Tested against these
strains, cefoxitin antagonized many other beta-lactam antibiotics.
Antagonism between the enzyme-stable beta-lactams (e.g. cefoxitin)
and mezlocillin and related drugs occurs because the former
antibiotics function as inducers of beta-lactamases. The mechanism
for antagonism is that the drug-induced beta-lactamase hydrolyzes
the antagonized beta-lactam. As a result, enzyme-stable beta-lactam
antibiotics have the potential ability to antagonize many other
antibiotics of this group. These types of beta-lactam antibiotics have
been used together in certain clinical situations, but there is little
evidence that such combinations are advantageous, and because of
potential antagonism they should be avoided (Sanders, 1983;
Gutmann et al., 1986).


Other pharmacological effects



Medicinal Chemistry


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

SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(c3ccccc3)NC(=O)N4CCN(C4=O)S(=O)(=O)C)C(=O)O)C

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

ACD/LogP: -1.183 # of Rule of 5 Violations: 2
ACD/LogD (pH 5.5): -4.16 ACD/LogD (pH 7.4): -4.91
ACD/BCF (pH 5.5): 1.00 ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 5.5): 1.00 ACD/KOC (pH 7.4): 1.00
#H bond acceptors: 13 #H bond donors: 3
#Freely Rotating Bonds: 6 Polar Surface Area: 207.18 Å2
Index of Refraction: 1.701 Molar Refractivity: 127.904 cm3
Molar Volume: 330.408 cm3 Polarizability: 50.705 10-24cm3
Surface Tension: 88.9830017089844 dyne/cm Density: 1.633 g/cm3
Flash Point: °C Enthalpy of Vaporization: kJ/mol
Boiling Point: °C at 760 mmHg Vapour Pressure: mmHg at 25°C


Major Impurities:


Melting point:

Optical rotation:


logP: 2.41




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