Mezlocillin

Mezlocillin

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%)
Half-life	1.3–4.4 hours
Excretion	Renal (50%) and biliary
Identifiers
CAS Registry Number	51481-65-3 Y
ATC code	J01CA10
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
Y (what is this?)  (verify)

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

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.

External links

• DDB 30377
• -288358398 at GPnotebook
• Duke
• Kristof R, Clusmann H, Koehler W, Fink K, Schramm J (1998). "Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange.". J Neurol Neurosurg Psychiatry 64 (3): 379–81. doi:10.1136/jnnp.64.3.379. PMC 2170014. PMID 9527154. 
• McCormick P, Greenslade L, Kibbler C, Chin J, Burroughs A, McIntyre N (1997). "A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients.". Hepatology 25 (4): 833–6. doi:10.1002/hep.510250408. PMID 9096584. 
• Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B (1997). "Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure.". Eur J Clin Pharmacol 53 (2): 111–5. doi:10.1007/s002280050347. PMID 9403281.