Mezlocillin

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 cat. B

Legal status ?

Routes 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 number 51481-65-3^Y

ATC code J01CA10

PubChem CID 656511

DrugBank APRD01113

ChemSpider 570894^Y

UNII OH2O403D1G^N

KEGG D05021^Y

ChEBI CHEBI:6919^N

ChEMBL CHEMBL1731^Y

Chemical data

Formula C₂₁H₂₅N₅O₈S₂

Mol. mass 539.584 g/mol

SMILES eMolecules & PubChem

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

N(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.

Contents

1 Mechanism of action

2 Susceptible organisms

2.1 Gram-negative

2.2 Gram-positive

3 External links

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.

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2170014.

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.

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/
(cephems)

1st (P Ec K)

Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)

Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd

Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)

Cefepime • Cefozopran • Cefpirome • Cefquinome

5th

Ceftobiprole • Ceftaroline fosamil

Veterinary

Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Tabtoxin

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam
Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

Categories:
Antibiotic stubs
Beta-lactam antibiotics
Enantiopure drugs
Imidazolidinones

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 cat.	B
Legal status	?
Routes	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 number	51481-65-3^Y
ATC code	J01CA10
PubChem	CID 656511
DrugBank	APRD01113
ChemSpider	570894^Y
UNII	OH2O403D1G^N
KEGG	D05021^Y
ChEBI	CHEBI:6919^N
ChEMBL	CHEMBL1731^Y
Chemical data
Formula	C₂₁H₂₅N₅O₈S₂
Mol. mass	539.584 g/mol
SMILES	eMolecules & PubChem
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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Look at other dictionaries:

Mezlocillin — См. Мезлоциллин (Источник: «Словарь терминов микробиологии») … Словарь микробиологии
mezlocillin — /mez leuh sil in/, n. Pharm. a wide spectrum semisynthetic penicillin, C21H25N5O8S2, used parenterally in the treatment of infections due to Pseudomonas aeruginosa. [ME(THYL) + (IMIDA)ZOL(E) (rearranged), components of the chemical name +… … Universalium
mezlocillin — /mez leuh sil in/, n. Pharm. a wide spectrum semisynthetic penicillin, C21H25N5O8S2, used parenterally in the treatment of infections due to Pseudomonas aeruginosa. [ME(THYL) + (IMIDA)ZOL(E) (rearranged), components of the chemical name +… … Useful english dictionary
mezlocillin sodium — C21H24NaN5O8S2; an extended spectrum penicillin antibiotic used intravenously and intramuscularly. * * * mez·lo·cil·lin so·di·um (mez″lo silґin) [USP] a semisynthetic, broad spectrum penicillin of the ureidopenicillin group, effective… … Medical dictionary
Dietmar Wittmann — Dietmar H. Wittmann, M.D., Ph.D., FACS is an academic surgeon specializing in complex abdominal surgery. He was associated with the following medical schools: University of Hamburg, Germany, University of Düsseldorf, Germany, University of… … Wikipedia
Ampicillin — Systematic (IUPAC) name (2S,5R,6R) 6 ([(2R) 2 amino 2 phenylace … Wikipedia
Amoxicillin — Systematic (IUPAC) name (2S,5R,6R) 6 … Wikipedia
Penicillin — For the Japanese band, see Penicillin (band). Penicillin core structure. The R is the variable group. Penicillin (sometimes abbreviated PCN or pen) is a group of antibiotics derived from Penicillium fungi.[1] They include … Wikipedia
Beta-lactam antibiotic — β lactam antibiotics are a broad class of antibiotics that include penicillin derivatives, cephalosporins, monobactams, carbapenems, and β lactamase inhibitors, that is, any antibiotic agent that contains a β lactam nucleus in its molecular… … Wikipedia
Timeline of antibiotics — This is the timeline of antimicrobial (anti infective) therapy.The years show when given antibiotic was released onto the pharmaceuticalmarket.* 1910 Arsphenamine aka Salvarsan * 1912 Neosalvarsan * 1935 Prontosil (an oral precursor to… … Wikipedia

Academic Dictionaries and Encyclopedias

Mezlocillin

Contents

Mechanism of action

Susceptible organisms

Gram-negative

Gram-positive

External links

Look at other dictionaries:

Share the article and excerpts

1st (P Ec K)	Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)	Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd	Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)	Cefepime • Cefozopran • Cefpirome • Cefquinome

5th	Ceftobiprole • Ceftaroline fosamil

Veterinary	Ceftiofur • Cefquinome • Cefovecin

Academic Dictionaries and Encyclopedias

Wikipedia

Mezlocillin

Contents

Mechanism of action

Susceptible organisms

Gram-negative

Gram-positive

External links

Look at other dictionaries:

Share the article and excerpts

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