Mupirocin: Difference between revisions

Jump to navigation Jump to search
VisualWikitext
No edit summary
Line 6: Line 6:
'''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''' ('''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>
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.
==Category==
==Category==
Pseudomonic acid
Pseudomonic acid

Revision as of 04:53, 9 January 2014

Mupirocin
BACTROBAN ® FDA Package Insert
Description
Clinical Pharmacology
Microbiology
Indications and Usage
Contraindications
Warnings and Precautions
Adverse Reactions
Drug Interactions
Overdosage
Dosage and Administration
How Supplied
Labels and Packages

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.

Category

Pseudomonic acid

US Brand Names

BACTROBAN®

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

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.[7] The inhibition of RNA synthesis was shown to be a protective mechanism in response to a lack of one amino acid, isoleucine.[8] 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.[9]

References

  1. ↑ Mupirocin by antimicrobe.org Editorial Board. Retrieved June 2012
  2. ↑ 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)
  3. ↑ 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. ↑ 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)
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Hughes J, Mellows G (1978). "On the mode of action of pseudomonic acid: inhibition of protein synthesis in Staphylococcus aureus". J. Antibiot. 31 (4): 330–5. PMID 659331. Unknown parameter |month= ignored (help)
  8. ↑ 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)
  9. ↑ 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)
Retrieved from "https://www.wikidoc.org/index.php?title=Mupirocin&oldid=929396"