Mezlocillin

Mezlocillin
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	B;
Routes of; administration	Intravenous, intramuscular
ATC code	J01CA10 (WHO) ;
Pharmacokinetic data
Protein binding	16–59%
Metabolism	Hepatic (20–30%)
Elimination half-life	1.3–4.4 hours
Excretion	Renal (50%) and biliary
Identifiers
	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;
CAS Number	51481-65-3 ;
PubChem CID	656511;
DrugBank	DB00948 ;
ChemSpider	570894 ;
UNII	OH2O403D1G;
KEGG	D05021 ;
ChEBI	CHEBI:6919 ;
ChEMBL	ChEMBL1731 ;
CompTox Dashboard (EPA)	DTXSID1023316 ;
ECHA InfoCard	100.052.013
Chemical and physical data
Formula	C21H25N5O8S2
Molar mass	539.58 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:YPBATNHYBCGSSN-VWPFQQQWSA-N ;
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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 cholangitis.

Mechanism of action

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.^{[citation needed]}

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

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.^{[citation needed]}

The closely related analogue azlocillin is made in essentially the same manner as mezlocillin. but with omission of the methylation step.^{[citation needed]}

References

^ W. Schroeck, H. R. Furtwaengier, H. B. Koenig, and K. G.Metzer, German Offen. 2,318,955 (1973); Chem. Abstr., 82,31313b (1975).
^ H. B. Koenig, K. G. Metzer, H. A. Offe, and W. Schroeck, Eur. J_. Med. Chem., 17, 59 (1982).

External links

Diseases Database (DDB): 30377
Duke

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[1] W. Schroeck, H. R. Furtwaengier, H. B. Koenig, and K. G.Metzer, German Offen. 2,318,955 (1973); Chem. Abstr., 82,31313b (1975).

[2] H. B. Koenig, K. G. Metzer, H. A. Offe, and W. Schroeck, Eur. J_. Med. Chem., 17, 59 (1982).

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