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Mezlocillin

Mezlocillin structure

CAS No:
51481-65-3
Formula:
C21H25N5O8S2
Chemical Name:
Mezlocillin
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-[[(2R)-2-[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]-2-phenylacetyl]amino]-7-oxo-,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-[[[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]phenylacetyl]amino]-7-oxo-,[2S-[2α,5α,6β(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-[[(2R)-[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]phenylacetyl]amino]-7-oxo-,(2S,5R,6R)-;(2S,5R,6R)-3,3-Dimethyl-6-[[(2R)-2-[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]-2-phenylacetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Mezlocillin;BAY-f 1353
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido group.

Solid

Mezlocillin is a penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a mezlocillin(1-).|Semisynthetic ampicillin-derived acylureido penicillin. It has been proposed for infections with certain anaerobes and may be useful in inner ear, bile, and CNS infections.|Mezlocillin is a broad-spectrum, beta-lactam penicillin antibiotic with antibacterial activity. Mezlocillin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts the final stage of bacterial cell wall synthesis and results in the weakening of the bacterial cell wall and eventually causing cell lysis.

Mezlocillin Basic Attributes

Molecular Weight：

539.58

Exact Mass：

539.58

EC Number：

257-233-8

UNII：

OH2O403D1G

DSSTox ID：

DTXSID1023316

NCI Thesaurus Code：

C653

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

207

XLogP3：

Appearance：

Solid

Density：

1.6±0.1 g/cm3

Boiling Point：

655.5ºC at 760 mmHg

Flash Point：

350.2ºC

Refractive Index：

1.701

Water Solubility：

4.71e-01 g/L

Toxicity

Toxicity Summary：

Symptoms of overdose include rash, fever, chills, and peeling skin.

Protein Binding：

16-59%

Drug Information

Drug Indication：

Used to treat serious gram–negative infections of the lungs, urinary tract, and skin.

Pharmacology：

Mezlocillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Mezlocillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of mezlocillin results from the inhibition of cell wall synthesis and is mediated through mezlocillin binding to penicillin binding proteins (PBPs). Mezlocillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Mezlocillin can be used to treat susceptible strains of H. influenzae, Klebsiella species, Pseudomonas species, Proteus mirabilis, E. coli, Enterobacter species, Streptococcus faecelis, Peptococcus species, Peptostreptococcus species, Bacteriodes species (including B. fragilis), Morganella morganii, Serratia species, N. gonorrhoeae, P. vulgaris, and Providencia rettgeri. This drug is discontinued in the U.S.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Metabolism/Metabolites：

Unlike many other penicillins, mezlocillin is either extensively metabolized or is subject to biliary excretion, as only about 50% of the dose was accounted for in normal urine.

Biological Half-Life：

1.3 to 4.4 hours

Mechanism of Action：

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, mezlocillin 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 mezlocillin interferes with an autolysin inhibitor.

MeSH Entry Terms：

Bay f 1353

Mezlocillin Use and Manufacturing

Uses

Semi-synthetic broad-spectrum penicillin, strong against Pseudomonas aeruginosa, Proteus, Escherichia coli, etc.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:539.6
XLogP3:-0.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:539.11445512
Monoisotopic Mass:539.11445512
Topological Polar Surface Area:207
Heavy Atom Count:36
Complexity:1080
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a semi-synthetic penicillin antibiotic. It has antibacterial effects on Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, Proteus, Enterobacter, Citrobacter, Serratia, Acinetobacter, and Gram-positive cocci sensitive to penicillin. It has a bactericidal effect in large doses. Its antibacterial activity against Escherichia coli, Enterobacter, Klebsiella pneumoniae, Citrobacter, Serratia, and Acinetobacter is stronger than carbenicillin and ampicillin; its antibacterial activity against indole-positive Proteus and Pseudomonas aeruginosa is stronger than carbenicillin and sulbenicillin; its antibacterial activity against Gram-positive bacteria such as Staphylococcus aureus is similar to that of carbenicillin, and its antibacterial activity against Streptococcus faecalis is superior to that of carbenicillin and sulbenicillin. It has good antibacterial effect on most anaerobic bacteria such as Bacteroides fragilis. In vitro tests of this product show that it is unstable to (lactamase produced by bacteria. This product has a significant synergistic effect when used in combination with aminoglycoside antibiotics such as gentamicin and kanamycin.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Mezlocillin Sodium for Injection
Ingredients	The main ingredient of this product is mezlocillin, and its chemical name is (2S, 5R, 6R)-3,3-dimethyl-6-[(R)-2[3-(methylsulfonyl)-2-oxo-1-imidazolidinecarboxamido]-2-phenylacetylamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylic acid sodium salt.
Indication	1. Antibiotics such as chloramphenicol, erythromycin, tetracyclines and antibacterial agents such as sulfonamides can interfere with the bactericidal activity of this product and should not be used in combination with this product, especially in the treatment of meningitis or severe infections that urgently require bactericides. 2. Probenecid, aspirin, indomethacin, phenylbutazone, and sulfonamides can reduce the excretion of this product from the kidneys. Therefore, when used in combination with this product, its blood concentration increases, the excretion time is prolonged, and the toxicity may also increase. 3. This product is incompatible with heavy metals, especially copper, zinc and mercury, because the latter can destroy its oxidized thiazole ring. Rubber tubes or bottle stoppers made of zinc compounds can also affect its activity. It can also be inactivated by oxidants, reducing agents or hydroxyl compounds. 4. This product will become turbid after adding cephalothin, lincomycin, tetracycline, vancomycin, erythromycin ethylsuccinate, amphotericin B, norepinephrine, metaraminol, phenytoin sodium, hydroxyzine hydrochloride, prochlorperazine, promethazine, vitamin B group, vitamin C, etc. to the intravenous infusion. 5. Avoid compatibility with drugs with strong acidity and alkalinity. Precipitation will occur below pH 4.5, and the potency will decrease rapidly below pH 4.0 and above pH 8.0. 6. This product can enhance the effect of warfarin. 7. It has a synergistic effect when used in combination with aminoglycoside antibiotics, but after mixing, the antibacterial activity of the two drugs is significantly weakened, so the two drugs cannot be placed in the same container for administration.
Specifications	1.0g (calculated as C21H25N5O8S2)
Manufacturer	North China Pharmaceutical Company.Ltd

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Mezlocillin 51481-65-3

CAS No.: 51481-65-3

Grade: Pharmaceutical Grade

Content: 99%

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