Mezlocillin: Difference between revisions

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{{drugbox
{{Drugbox
| verifiedrevid = 462252118
| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-6-<nowiki>[[</nowiki>(2''R'')-2-[(3-methylsulfonyl-<br>2-oxo-imidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]<br>amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-<br>carboxylic acid
| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-6-<nowiki>[[</nowiki>(2''R'')-2-[(3-methylsulfonyl-<br>2-oxo-imidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]<br>amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-<br>carboxylic acid
| image = Mezlocillin.svg
| image = Mezlocillin.svg
| CAS_number = 51481-65-3
 
| ATC_prefix = J01
<!--Clinical data-->
| ATC_suffix = CA10
| tradename =
| ATC_supplemental =  
| Drugs.com = {{drugs.com|CONS|mezlocillin}}
| PubChem = 656511
| DrugBank = APRD01113
| C = 21 | H = 25 | N = 5 | O = 8 | S = 2
| molecular_weight = 539.584 g/mol
| bioavailability =
| protein_bound = 16–59%
| metabolism = [[Liver|Hepatic]] (20–30%)
| elimination_half-life = 1.3–4.4 hours
| excretion = [[Kidney|Renal]] (50%) and biliary
| pregnancy_category = B
| pregnancy_category = B
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  
| legal_status =
| routes_of_administration = [[Intravenous therapy|Intravenous]], [[Intramuscular injection|intramuscular]]
| routes_of_administration = [[Intravenous therapy|Intravenous]], [[Intramuscular injection|intramuscular]]
}}
{{SI}}


<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 16–59%
| metabolism = [[Liver|Hepatic]] (20–30%)
| elimination_half-life = 1.3–4.4 hours
| excretion = [[Kidney|Renal]] (50%) and biliary
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 51481-65-3
| ATC_prefix = J01
| ATC_suffix = CA10
| ATC_supplemental = 
| PubChem = 656511
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00948
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 570894
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = OH2O403D1G
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05021
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6919
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1731


'''Mezlocillin''' is a broad-spectrum [[penicillin]] [[antibiotic]]. It is active against both [[Gram-negative]] and some [[Gram-positive]] [[bacteria]].
<!--Chemical data-->
| C=21 | H=25 | N=5 | O=8 | S=2
| molecular_weight = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YPBATNHYBCGSSN-VWPFQQQWSA-N
}}
'''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==
==Mechanism of action==
Line 49: Line 74:
===Gram-positive===
===Gram-positive===
*''[[Enterococcus faecalis]]''
*''[[Enterococcus faecalis]]''
*''[[Peptococcus]] spp.''
*''[[Peptococcus]]'' spp.''
*''[[Peptostreptococcus]] spp.''
*''[[Peptostreptococcus]]'' spp.''


==External links==
==External links==
Line 56: Line 81:
* {{GPnotebook|-288358398}}
* {{GPnotebook|-288358398}}
* [http://www.wheelessonline.com/ortho/mezlocillin_mezlin Duke]
* [http://www.wheelessonline.com/ortho/mezlocillin_mezlin Duke]
* {{cite journal | author = Kristof R, Clusmann H, Koehler W, Fink K, Schramm J | title = Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. | journal = J Neurol Neurosurg Psychiatry | volume = 64 | issue = 3 | pages = 379-81 | year = 1998 | id = PMID 9527154}}
* {{cite journal | author = Kristof R, Clusmann H, Koehler W, Fink K, Schramm J | title = Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. | journal = J Neurol Neurosurg Psychiatry | volume = 64 | issue = 3 | pages = 379–81 | year = 1998 | pmid = 9527154 | doi = 10.1136/jnnp.64.3.379 | pmc = 2170014}}
* {{cite journal | author = McCormick P, Greenslade L, Kibbler C, Chin J, Burroughs A, McIntyre N | title = A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. | journal = Hepatology | volume = 25 | issue = 4 | pages = 833-6 | year = 1997 | id = PMID 9096584}}
* {{cite journal | author = McCormick P, Greenslade L, Kibbler C, Chin J, Burroughs A, McIntyre N | title = A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. | journal = Hepatology | volume = 25 | issue = 4 | pages = 833–6 | year = 1997 | pmid = 9096584 | doi = 10.1002/hep.510250408}}
* {{cite journal | author = Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B | title = Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. | journal = Eur J Clin Pharmacol | volume = 53 | issue = 2 | pages = 111-5 | year = 1997 | id = PMID 9403281}}
* {{cite journal | author = Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B | title = Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. | journal = Eur J Clin Pharmacol | volume = 53 | issue = 2 | pages = 111–5 | year = 1997 | pmid = 9403281 | doi = 10.1007/s002280050347}}


{{antibiotic-stub}}
{{PenicillinAntiBiotics}}
{{PenicillinAntiBiotics}}
[[Category:Beta-lactam antibiotics]]
[[Category:Beta-lactam antibiotics]]
 
[[Category:Enantiopure drugs]]
 
[[Category:Imidazolidinones]]
 
{{WH}}
{{WikiDoc Sources}}

Revision as of 14:39, 13 April 2015

Mezlocillin
File:Mezlocillin.svg
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • B
Routes of
administration		Intravenous, intramuscular
ATC code
Pharmacokinetic data
Protein binding16–59%
MetabolismHepatic (20–30%)
Elimination half-life1.3–4.4 hours
ExcretionRenal (50%) and biliary
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC21H25N5O8S2
Molar mass539.584 g/mol
3D model (JSmol)
  (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

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

Gram-positive

External links

  • Template:DiseasesDB
  • Template: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.

Template:Antibiotic-stub

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