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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
{{Cefamandole}}
| image            = Cefamandole.svg
{{CMG}}
| 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}}
{{EH}}


'''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]].
{{SK}} Cephamandole


Cefamandole is no longer available in the United States.
==Overview==


{{CephalosporinAntiBiotics}}
Cefamandole 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]].


[[Category:Cephalosporin antibiotics]]
Cefamandole is [[List of withdrawn drugs|no longer available]] in the United States.
{{SIB}}


{{WikiDoc Help Menu}}
==Category==
{{WS}}
 
Cephalosporin, Second-Generation
 
==US Brand Names==
 
MANDOL<sup>®</sup> (''DISCONTINUED'')
 
==FDA Package Insert==
 
'''  [[Cefamandole description|Description]]'''
'''| [[Cefamandole clinical pharmacology|Clinical Pharmacology]]'''
'''| [[Cefamandole microbiology|Microbiology]]'''
'''| [[Cefamandole indications and usage|Indications and Usage]]'''
'''| [[Cefamandole contraindications|Contraindications]]'''
'''| [[Cefamandole warnings and precautions|Warnings and Precautions]]'''
'''| [[Cefamandole adverse reactions|Adverse Reactions]]'''
'''| [[Cefamandole drug interactions|Drug Interactions]]'''
'''| [[Cefamandole overdosage|Overdosage]]'''
'''| [[Cefamandole clinical studies|Clinical Studies]]'''
'''| [[Cefamandole dosage and administration|Dosage and Administration]]'''
'''| [[Cefamandole how supplied|How Supplied]]'''
'''| [[Cefamandole labels and packages|Labels and Packages]]'''
 
==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
 
==Adverse Reactions==
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]].
 
==Report==
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>
 
==Mechanism of Action==
 
Cefamandole, as a second-generation cephalosporin, binds to specific [[penicillin-binding protein]]s (PBPs) and inhibits bacterial [[cell wall]] synthesis.
 
==References==
 
{{Reflist|2}}
 
[[Category:Antibiotics]]
[[Category:Wikinfect]]

Latest revision as of 00:15, 6 January 2014

Cefamandole
MANDOL® FDA Package Insert
Description
Clinical Pharmacology
Microbiology
Indications and Usage
Contraindications
Warnings and Precautions
Adverse Reactions
Drug Interactions
Overdosage
Dosage and Administration
How Supplied

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

Synonyms and keywords: Cephamandole

Overview

Cefamandole is a second-generation broad-spectrum cephalosporin antibiotic. 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.

Category

Cephalosporin, Second-Generation

US Brand Names

MANDOL® (DISCONTINUED)

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

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.

Adverse Reactions

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.

Report

CO2 is generated during the normal constitution of cefamandole & ceftazidim resulting in explosive like reaction in syringe.[1]

Mechanism of Action

Cefamandole, as a second-generation cephalosporin, binds to specific penicillin-binding proteins (PBPs) and inhibits bacterial cell wall synthesis.

References

  1. 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.