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{{Drugbox
__NOTOC__
| IUPAC_name        = (6''R'',7''R'')-7-{[(2''R'')-2-hydroxy-2-phenylacetyl]amino}-<br>3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-<br>5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic&nbsp;acid
{{CMG}}
| image            = Cefamandole.svg
| CAS_number        = 34444-01-4
| CAS_supplemental  = {{CAS|42540-40-9}} (nafate)
| ATC_prefix        = J01
| ATC_suffix        = DC03
| PubChem          = 456255
| DrugBank          =
| C=18|H=18|N=6|O=5|S=2
| molecular_weight  = 462.505 g/mol
| bioavailability  =
| protein_bound    = 75%
| metabolism        =
| elimination_half-life = 48 minutes
| excretion        = Mostly [[kidney|renal]], as unchanged drug
| pregnancy_AU      = B1
| pregnancy_US      =  <!-- A / B            / C / D / X -->
| pregnancy_category= 
| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA          =  <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK          =  POM
| legal_US          =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status      = Discontinued <small>([[United States|US]])</small>
| routes_of_administration = [[Intramuscular injection|Intramuscular]], [[intravenous therapy|intravenous]]
}}
{{SI}}


{{SK}} Cephamandole


'''Cefamandole''' ([[International Nonproprietary Name|INN]], also known as '''cephamandole''') is a [[broad-spectrum antibiotic|broad-spectrum]] [[cephalosporin]] [[antibiotic]]. The clinically used form of cefamandole is the [[formate]] [[ester]] '''cefamandole nafate''', a [[prodrug]] which is administered [[wikt:parenteral|parenterally]].
==Overview==


Cefamandole is no longer available in the United States.
Cefamandole ([[International Nonproprietary Name|INN]], also known as cephamandole) is a second-generation [[broad-spectrum antibiotic|broad-spectrum]] [[cephalosporin]][[antibiotic]]. The clinically used form of cefamandole is the [[formate]] [[ester]] '''cefamandole nafate''', a [[prodrug]] which is administered [[wikt:parenteral|parenterally]].


{{CephalosporinAntiBiotics}}
Cefamandole is [[List of withdrawn drugs|no longer available]] in the United States.


[[Category:Cephalosporin antibiotics]]
== Adverse effects ==
The chemical structure of cefamandole, like that of several other cephalosporins, contains an ''N''-methylthiotetrazole (NMTT or 1-MTT) [[side chain]]. As the antibiotic is broken down in the body, it releases free NMTT, which can cause [[hypoprothrombinemia]] (likely due to [[enzyme inhibitor|inhibition]] of the [[enzyme]] [[vitamin K epoxide reductase]])(vitamin K supplement is recommended during therapy) and a reaction with ethanol similar to that produced by [[disulfiram]] (Antabuse), due to inhibition of [[aldehyde dehydrogenase]].


==Spectrum of Bacterial Susceptibility==
Cefamandole has a broad spectrum of activity and can be used to treat bacterial infections of the skin, bones and joints, urinary tract, and lower respiratory tract. The following represents cefamandole MIC susceptibility data for a few medically significant microorganisms.
* ''Escherichia coli'': 0.12 μg/mL - 400 μg/mL
* ''Haemophilus influenzae'': 0.06 μg/mL - >16 μg/mL
* ''Staphylococcus aureus'': 0.1 μg/mL - 12.5 μg/mL
<ref>http://www.toku-e.com/Assets/MIC/Cefamandole%20sodium%20salt.pdf</ref>


{{WikiDoc Help Menu}}
==Report==
{{WS}}
CO2 is generated during the normal constitution of cefamandole & ceftazidim resulting in explosive like reaction in syringe
 
<ref name=Goldfrank>{{cite book |author=Stork CM |editor=Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.) |title=Goldfrank's toxicologic emergencies|chapter=Antibiotics, antifungals, and antivirals |chapterurl=http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847 |publisher=McGraw-Hill |location=New York |year=2006 |pages=847|isbn=0-07-143763-0 |accessdate=2009-07-03}}</ref>
 
 
 
==Category==
 
==US Brand Names==
 
==FDA Package Insert==
 
'''  [[XXXXX description|Description]]'''
'''| [[XXXXX clinical pharmacology|Clinical Pharmacology]]'''
'''| [[XXXXX microbiology|Microbiology]]'''
'''| [[XXXXX indications and usage|Indications and Usage]]'''
'''| [[XXXXX contraindications|Contraindications]]'''
'''| [[XXXXX warnings and precautions|Warnings and Precautions]]'''
'''| [[XXXXX adverse reactions|Adverse Reactions]]'''
'''| [[XXXXX drug interactions|Drug Interactions]]'''
'''| [[XXXXX overdosage|Overdosage]]'''
'''| [[XXXXX clinical studies|Clinical Studies]]'''
'''| [[XXXXX dosage and administration|Dosage and Administration]]'''
'''| [[XXXXX how supplied|How Supplied]]'''
'''| [[XXXXX labels and packages|Labels and Packages]]'''
 
==Mechanism of Action==
 
==References==
 
{{Reflist|2}}
 
[[Category:Antibiotics]]
[[Category:Wikinfect]]

Revision as of 23:39, 5 January 2014

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Synonyms and keywords: Cephamandole

Overview

Cefamandole (INN, also known as cephamandole) is a second-generation broad-spectrum cephalosporinantibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally.

Cefamandole is no longer available in the United States.

Adverse effects

The chemical structure of cefamandole, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase)(vitamin K supplement is recommended during therapy) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.

Spectrum of Bacterial Susceptibility

Cefamandole has a broad spectrum of activity and can be used to treat bacterial infections of the skin, bones and joints, urinary tract, and lower respiratory tract. The following represents cefamandole MIC susceptibility data for a few medically significant microorganisms.

  • Escherichia coli: 0.12 μg/mL - 400 μg/mL
  • Haemophilus influenzae: 0.06 μg/mL - >16 μg/mL
  • Staphylococcus aureus: 0.1 μg/mL - 12.5 μg/mL

[1]

Report

CO2 is generated during the normal constitution of cefamandole & ceftazidim resulting in explosive like reaction in syringe

[2]


Category

US Brand Names

FDA Package Insert

Description | Clinical Pharmacology | Microbiology | Indications and Usage | Contraindications | Warnings and Precautions | Adverse Reactions | Drug Interactions | Overdosage | Clinical Studies | Dosage and Administration | How Supplied | Labels and Packages

Mechanism of Action

References

  1. http://www.toku-e.com/Assets/MIC/Cefamandole%20sodium%20salt.pdf
  2. Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.