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%)
Biological 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^Y
PubChem (CID)	656511
DrugBank	DB00948^Y
ChemSpider	570894^Y
UNII	OH2O403D1G^Y
KEGG	D05021^Y
ChEBI	CHEBI:6919^Y
ChEMBL	CHEMBL1731^Y
ECHA InfoCard	100.052.013
Chemical and physical data
Formula	C₂₁H₂₅N₅O₈S₂
Molar mass	539.584 g/mol
3D model (Jmol)	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^Y Key:YPBATNHYBCGSSN-VWPFQQQWSA-N^Y

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.

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.

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.

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Wikipedia