Mezlocillin

Mezlocillin

File:Mezlocillin.svg
Systematic (IUPAC) 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
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	B
Routes of administration	Intravenous, intramuscular
Pharmacokinetic data
Protein binding	16–59%
Metabolism	Hepatic (20–30%)
Biological half-life	1.3–4.4 hours
Excretion	Renal (50%) and biliary
Identifiers
CAS Number	51481-65-3 Y
ATC code	J01CA10 (WHO)
PubChem	CID: 656511
DrugBank	DB00948 Y
ChemSpider	570894 Y
UNII	OH2O403D1G Y
KEGG	D05021 Y
ChEBI	CHEBI:6919 Y
ChEMBL	CHEMBL1731 Y
Chemical data
Formula	C21H25N5O8S2
Molecular mass	539.584 g/mol
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)N(S(=O)(=O)C)CC2)[C@H]4SC3(C)C
InChI 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 Y Key:YPBATNHYBCGSSN-VWPFQQQWSA-N Y
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Mezlocillin is a broad-spectrum penicillin antibiotic. 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.

Mechanism of action

Main article: Beta-lactam antibiotic

Like all other beta-lactam antibiotics, mezlocillin inhibits the third and last stage of bacterial cell wall synthesis by binding to penicillin binding proteins. This ultimately leads to cell lysis.

Susceptible organisms

Gram-negative

• Bacteroides spp., including B. fragilis
• Enterobacter spp.
• Escherichia coli
• Haemophilus influenzae
• Klebsiella species
• Morganella morganii
• Neisseria gonorrhoeae
• Proteus mirabilis
• Proteus vulgaris
• Providencia rettgeri
• Pseudomonas spp., including P. aeruginosa
• Serratia marcescens

Gram-positive

• Enterococcus faecalis
• Peptococcus spp.
• Peptostreptococcus spp.

Synthesis

File:Mezlocillin synthesis.svg

Mezlocillin synthesis:

Mezlocillin can be made in a variety of ways including reaction of ampicillin with chlorocarbamate 1 in the presence of triethylamine. Chlorocarbamate 1 itself is made from ethylenediamine by reaction with phosgene to form the cyclic urea followed by monoamide formation with methanesulfonyl chloride and then reaction of the other nitrogen atom with phosgene and trimethylsilylchloride.

The closely related analogue azlocillin is made in essentially the same manner as mezlocillin. but with omission of the methylation step.

External links

• DDB 30377

• -288358398 at GPnotebook
• Duke