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__NOTOC__ | |||
{{Mupirocin}} | |||
{{CMG}}; {{AE}} {{chetan}} | |||
{{ | ==Overview== | ||
'''Mupirocin''' ('''Bactroban''' or '''Centany''') is an [[antibiotic]] of the [[monoxycarbolic acid]] class.<ref>[http://www.antimicrobe.org/drugpopup/Mupirocin.pdf Mupirocin] by [http://www.antimicrobe.org/editorial-board.htm antimicrobe.org Editorial Board]. Retrieved June 2012</ref> It was originally isolated from ''[[Pseudomonas fluorescens]]'' NCIMB 10586,<ref name="pmid5003547">{{cite journal |author=Fuller AT, Mellows G, Woolford M, Banks GT, Barrow KD, Chain EB |title=Pseudomonic acid: an antibiotic produced by Pseudomonas fluorescens |journal=Nature |volume=234 |issue=5329 |pages=416–7 |year=1971 |month=December |pmid=5003547 |doi= 10.1038/234416a0 }}</ref> developed by [[Beecham (pharmaceutical company)|Beecham]]. | |||
Mupirocin is [[bacteriostatic]] at low concentrations and [[bactericidal]] at high concentrations.<ref>{{cite news | first=Kate | last=Moodabe | coauthors= Linda Bryant | title=Topical antibiotics - more harm than good? | date= | publisher= | url =http://www.rnzcgp.org.nz/news/nzfp/Oct2000/moodabe.htm | work =Focus | pages =1 | accessdate = 2007-04-20 | language = |archiveurl = http://web.archive.org/web/20070716134428/http://www.rnzcgp.org.nz/news/nzfp/Oct2000/moodabe.htm <!-- Bot retrieved archive --> |archivedate = 2007-07-16}}</ref> It is used topically and is effective against [[Gram-positive]] [[bacterium|bacteria]], including [[Methicillin-resistant Staphylococcus aureus|MRSA]].<ref name="pmid365175">{{cite journal |author=Hughes J, Mellows G |title=Inhibition of isoleucyl-transfer ribonucleic acid synthetase in Echerichia coli by pseudomonic acid |journal=Biochem. J. |volume=176 |issue=1 |pages=305–18 |year=1978 |month=October |pmid=365175 |doi= |pmc=1186229}}</ref> Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. Also present in mupirocin are pseudomonic acid B with an additional hydroxyl group at C8,<ref name="pmid402373">{{cite journal |author=Chain EB, Mellows G |title=Pseudomonic acid. Part 3. Structure of pseudomonic acid B |journal=J. Chem. Soc. Perkin Trans. I |volume= |issue=3 |pages=318–24 |year=1977 |pmid=402373 |doi= 10.1039/p19770000318 }}</ref> pseudomonic acid C with a double bond between C10 and C11, instead of the epoxide of PA-A,<ref name="urlScienceDirect - Tetrahedron Letters: The structure and configuration of pseudomonic acid C">{{cite journal |doi=10.1016/S0040-4039(00)71533-4 |title=ScienceDirect - Tetrahedron Letters: The structure and configuration of pseudomonic acid C |format= |work= |accessdate= |year=1980 |author=Clayton, J |journal=Tetrahedron Letters |volume=21 |pages=881 |issue=9 |last2=O'Hanlon |first2=Peter J. |last3=Rogers |first3=Norman H.}}</ref> and pseudomonic acid D with a double bond at C4` and C5` in the 9-hydroxy-nonanoic acid portion of mupirocin.<ref> | |||
==Category== | |||
Pseudomonic acid | |||
==US Brand Names== | |||
BACTROBAN<sup>®</sup> | |||
==FDA Package Insert== | |||
''' [[Mupirocin description|Description]]''' | |||
'''| [[Mupirocin clinical pharmacology|Clinical Pharmacology]]''' | |||
'''| [[Mupirocin microbiology|Microbiology]]''' | |||
'''| [[Mupirocin indications and usage|Indications and Usage]]''' | |||
'''| [[Mupirocin contraindications|Contraindications]]''' | |||
'''| [[Mupirocin warnings and precautions|Warnings and Precautions]]''' | |||
'''| [[Mupirocin adverse reactions|Adverse Reactions]]''' | |||
'''| [[Mupirocin drug interactions|Drug Interactions]]''' | |||
'''| [[Mupirocin overdosage|Overdosage]]''' | |||
'''| [[Mupirocin clinical studies|Clinical Studies]]''' | |||
'''| [[Mupirocin dosage and administration|Dosage and Administration]]''' | |||
'''| [[Mupirocin how supplied|How Supplied]]''' | |||
'''| [[Mupirocin labels and packages|Labels and Packages]]''' | |||
== | ==Mechanism of Action== | ||
Mupirocin reversibly binds to the isoleucyl t-RNA synthetase in ''[[Staphylococcus aureus]]'' and ''Streptococcus'', resulting in inhibition of protein synthesis. [[DNA]] and cell wall formation are also negatively impacted to a lesser degree.<ref name="pmid659331">{{cite journal |author=Hughes J, Mellows G |title=On the mode of action of pseudomonic acid: inhibition of protein synthesis in Staphylococcus aureus |journal=J. Antibiot. |volume=31 |issue=4 |pages=330–5 |year=1978 |month=April |pmid=659331 }}</ref> The inhibition of RNA synthesis was shown to be a protective mechanism in response to a lack of one [[amino acid]], [[isoleucine]].<ref name="pmid4576025">{{cite journal |author=Haseltine WA, Block R |title=Synthesis of Guanosine Tetra- and Pentaphosphate Requires the Presence of a Codon-Specific, Uncharged Transfer Ribonucleic Acid in the Acceptor Site of Ribosomes |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=70 |issue=5 |pages=1564–8 |year=1973 |month=May |pmid=4576025 |doi= 10.1073/pnas.70.5.1564|pmc=433543}}</ref> In vivo studies in ''[[Escherichia coli]]'' demonstrated that pseudomonic acid inhibits isoleucine [[Isoleucyl-tRNA synthetase|t-RNA synthetase]] (IleRS).<ref name="pmid365175"/> This mechanism of action is shared with [[furanomycin]], an analog of isoleucine.<ref name="pmid4982424">{{cite journal |author=Tanaka K, Tamaki M, Watanabe S |title=Effect of furanomycin on the synthesis of isoleucyl-tRNA |journal=Biochim. Biophys. Acta |volume=195 |issue=1 |pages=244–5 |year=1969 |month=November |pmid=4982424 }}</ref> | |||
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== | ==References== | ||
{{Reflist|2}} | |||
[[Category:Antibiotics]] | |||
[ | [[Category:Wikinfect]] | ||
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[[Category: | |||
Revision as of 04:52, 9 January 2014
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Chetan Lokhande, M.B.B.S [2]
Overview
Mupirocin (Bactroban or Centany) is an antibiotic of the monoxycarbolic acid class.[1] It was originally isolated from Pseudomonas fluorescens NCIMB 10586,[2] developed by Beecham.
Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.[3] It is used topically and is effective against Gram-positive bacteria, including MRSA.[4] Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. Also present in mupirocin are pseudomonic acid B with an additional hydroxyl group at C8,[5] pseudomonic acid C with a double bond between C10 and C11, instead of the epoxide of PA-A,[6] and pseudomonic acid D with a double bond at C4` and C5` in the 9-hydroxy-nonanoic acid portion of mupirocin. The inhibition of RNA synthesis was shown to be a protective mechanism in response to a lack of one amino acid, isoleucine.[7] In vivo studies in Escherichia coli demonstrated that pseudomonic acid inhibits isoleucine t-RNA synthetase (IleRS).[4] This mechanism of action is shared with furanomycin, an analog of isoleucine.[8]
References
- ↑ Mupirocin by antimicrobe.org Editorial Board. Retrieved June 2012
- ↑ Fuller AT, Mellows G, Woolford M, Banks GT, Barrow KD, Chain EB (1971). "Pseudomonic acid: an antibiotic produced by Pseudomonas fluorescens". Nature. 234 (5329): 416–7. doi:10.1038/234416a0. PMID 5003547. Unknown parameter
|month=ignored (help) - ↑ Moodabe, Kate. "Topical antibiotics - more harm than good?". Focus. p. 1. Archived from the original on 2007-07-16. Retrieved 2007-04-20. Unknown parameter
|coauthors=ignored (help) - ↑ 4.0 4.1 Hughes J, Mellows G (1978). "Inhibition of isoleucyl-transfer ribonucleic acid synthetase in Echerichia coli by pseudomonic acid". Biochem. J. 176 (1): 305–18. PMC 1186229. PMID 365175. Unknown parameter
|month=ignored (help) - ↑ Chain EB, Mellows G (1977). "Pseudomonic acid. Part 3. Structure of pseudomonic acid B". J. Chem. Soc. Perkin Trans. I (3): 318–24. doi:10.1039/p19770000318. PMID 402373.
- ↑ Clayton, J; O'Hanlon, Peter J.; Rogers, Norman H. (1980). "ScienceDirect - Tetrahedron Letters: The structure and configuration of pseudomonic acid C". Tetrahedron Letters. 21 (9): 881. doi:10.1016/S0040-4039(00)71533-4.
- ↑ Haseltine WA, Block R (1973). "Synthesis of Guanosine Tetra- and Pentaphosphate Requires the Presence of a Codon-Specific, Uncharged Transfer Ribonucleic Acid in the Acceptor Site of Ribosomes". Proc. Natl. Acad. Sci. U.S.A. 70 (5): 1564–8. doi:10.1073/pnas.70.5.1564. PMC 433543. PMID 4576025. Unknown parameter
|month=ignored (help) - ↑ Tanaka K, Tamaki M, Watanabe S (1969). "Effect of furanomycin on the synthesis of isoleucyl-tRNA". Biochim. Biophys. Acta. 195 (1): 244–5. PMID 4982424. Unknown parameter
|month=ignored (help)