MUPIROCIN

PRODUCT IDENTIFICATION
CAS NO. 12650-69-0MUPIROCIN
EINECS NO.  
FORMULA C26H44O9
MOL WT. 500.62

TOXICITY

 Oral Rat LD50: 5gm/kg

H.S. CODE

 2910.90.9000
SYNONYMS Bactroban; Centany;
(E)-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl)tetrahydro- 3,4-dihydroxy- beta-methyl-2H-pyran-2-crotonic acid 9-hydroxynonanoic acid ester; 8-Carboxyoctyl (E)-4-(2S,3R,4R,5S)- 5-((2S,3S,4S,5S)-2,3-epoxy-5 -hydroxy-4-methylhexyl)-3,4-dihydroxytetrahydro-2H -pyran-2-yl)- 3-methylcrotonate; Mupirocinum; Bactoderm; Plasimine; Mupirocin; Mupirocina; Mupirocine;  Pseudomonic acid;  Pseudomonic acid A;
SMILES C1[C@@H]([C@H]([C@H]([C@@H](O1)C\C(=C\C(OCCCCCCC CC(O)=O)=O)C)O)O)C[C@H]1[C@@H](O1)[C@H]([C@H](C)O)C

CLASSIFICATION

Anti-Infective, Antibacterial,

EXTRA NOTES

Antibiotic; inhibits isoleucyl-tRNA synthetase (IRS).
A topically used antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.  Pseudomonic acid; Pseudomonic acid  A;

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE

white to off-white powder

MELTING POINT

 

BOILING POINT

 

SPECIFIC GRAVITY  
SOLUBILITY IN WATER

 

SOLVENT SOLUBILITY

 

pH  
VAPOR DENSITY

 

REFRACTIVE INDEX

  

NFPA RATINGS

Health hazard: 1, Fire: 0, Reactivity Hazard: 0

AUTOIGNITION

 

FLASH POINT

 

STABILITY Stable under normal conditions.

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Mupirocin

PubChem Compound Summary - Mupirocin

http://www.antimicrobe.org/
Brand names/Manufacturer:

  • BACROCIN (ICN - BRAZIL)
  • BACTODERM (Agis - ISRAEL)
  • BACTROBAN (SmithKline Beecham – USA, CANADA, UK, IRELAND, NETHERLANDS, SOUTH AFRICA, FRANCE, BELGIUM, SPAIN, SWEDEN, AUSTRIA, SWITZERLAND, ITALY, AUSTRALIA, DENMARK, BRAZIL, JAPAN, HONG KONG, MEXICO, ISREAL, THAILAND, SINGAPORE, FINLAND, NEW ZEALAND, MALAYSIA, PORTUGAL, GREECE, CHILE, HUNGARY, CZECH REPUBLIC)
  • BACTRONEO (Neo Quimica - BRAZIL)
  • CELEFER (Smith Kline - Spain)
  • CENTANY (Ortho - USA)
  • EISMYCIN (GlaxoSmithKline - GERMANY)
  • EISMYCIN (SmithKline - GERMANY)
  • HEVRONAZ (Rafarm  - GREECE)
  • INFECTOPYODERM (Infectopharm  - GERMANY)
  • MICOBAN (Genepharm  - GREECE)
  • MUPIDERM (Pharmafarm - FRANCE)
  • MUPIROCIN (Teva - USA)
  • MUPORIN (TO-Chemicals - THAILAND)
  • PLASIMINE (Isdin - SPAIN)
  • TURIXIN (GlaxoSmithKline - GERMANY)
  • ULTRABIOTIC (Bago  - CHILE)
  • UNDERAN (Saval - CHILE)
  • VELTION (Faran - GREECE)

http://www.pnas.org/
Intraerythrocytic malaria parasites can obtain nearly their entire amino acid requirement by degrading host cell hemoglobin. The sole exception is isoleucine, which is not present in adult human hemoglobin and must be obtained exogenously. We evaluated two compounds for their potential to interfere with isoleucine utilization. Mupirocin, a clinically used antibacterial, kills Plasmodium falciparum parasites at nanomolar concentrations. Thiaisoleucine, an isoleucine analog, also has antimalarial activity. To identify targets of the two compounds, we selected parasites resistant to either mupirocin or thiaisoleucine. Mutants were analyzed by genome-wide high-density tiling microarrays, DNA sequencing, and copy number variation analysis. The genomes of three independent mupirocin-resistant parasite clones had all acquired either amplifications encompassing or SNPs within the chromosomally encoded organellar (apicoplast) isoleucyl-tRNA synthetase. Thiaisoleucine-resistant parasites had a mutation in the cytoplasmic isoleucyl-tRNA synthetase. The role of this mutation in thiaisoleucine resistance was confirmed by allelic replacement. This approach is generally useful for elucidation of new targets in P. falciparum. Our study shows that isoleucine utilization is an essential pathway that can be targeted for antimalarial drug development.

http://www.pidsphil.org/
THE EFFECT OF TOPICAL APPLICATION OF MUPIROCIN IN INTRAVENOUS CATHETER SITE IN THE INCIDENCE OF SUPERFICIAL PHLEBITIS

http://www.nature.com/
Mupirocin, a polyketide antibiotic produced by Pseudomonas fluorescens, is used to control the carriage of methicillin-resistant Staphylococcus aureus on skin and in nasal passages as well as for various skin infections. Low-level resistance to the antibiotic arises by mutation of the mupirocin target, isoleucyl-tRNA synthetase, whereas high-level resistance is due to the presence of an isoleucyl-tRNA synthetase with many similarities to eukaryotic enzymes. Mupirocin biosynthesis is carried out by a combination of type I multifunctional polyketide synthases and tailoring enzymes encoded in a 75 kb gene cluster. Chemical synthesis has also been achieved. This knowledge should allow the synthesis of new and modified antibiotics for the future. 
SALES SPECIFICATION

APPEARANCE

white to off-white powder

IDENTIFICATION

passes Test

PURITY

92.0% ~ 102.0%

pH

3.0 ~ 4.5

OPTICAL ROTATION

-20° ~ -16°

IMPURITY

Individual impurity 1.0% max
Total impurity: 5.0% max

RESIDUAL SOLVENTS

Ethyl Acetate 0.5% max
Isobutyl Acetate 0.5% max
Heptane 0.5% max
Acetone 0.5% max

WATER

1.0% max

HEAVY METALS

20ppm max
TRANSPORTATION
PACKING
 
HAZARD CLASS

 

UN NO. Not regulated
PRICE INFORMATION