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Substance Name: Mupirocin [USAN:USP:INN:BAN]
RN: 12650-69-0
UNII: D0GX863OA5
InChIKey: MINDHVHHQZYEEK-HBBNESRFSA-N

Note

  • 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.

Molecular Formula

  • C26-H44-O9

Molecular Weight

  • 500.6246
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial (Topical)
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Natural Product
  • Protein Synthesis Inhibitors

Names and Synonyms

Name of Substance

  • Mupirocin
  • Mupirocin [USAN:USP:INN:BAN]

MeSH Heading

  • Mupirocin

Synonyms

  • (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, ester with 9-hydroxynonanoic acid
  • 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-methylcrotonat
  • Bactoderm
  • Bactroban
  • Bactroban Ointment
  • BRL 4910A
  • Centany
  • Mupirocin
  • Mupirocin Neo-Sensitabs
  • Mupirocina
  • Mupirocina [Spanish]
  • Mupirocine
  • Mupirocine [French]
  • Mupirocinum
  • Mupirocinum [Latin]
  • Nonanoic acid, 9-((3-methyl-1-oxo-4-(tetrahydro-3,4-dihydroxy-5-((3-(2-hydroxy-1-methylpropyl)oxiranyl)methyl)-2H-pyran-2-yl)-2-butenyl)oxy)-, (2S-(2alpha(E),3beta,4beta,5alpha(2R*,3R*(1R*,2R*))))-
  • Plasimine
  • Pseudomonic acid
  • Pseudomonic acid A
  • trans-Pseudomonic acid
  • Turixin
  • UNII-D0GX863OA5

Systematic Name

  • Nonanoic acid, 9-((3-methyl-1-oxo-4-(tetrahydro-3,4-dihydroxy-5-((3-(2-hydroxy-1-methylpropyl)oxiranyl)methyl)-2H-pyran-2-yl)-2-butenyl)oxy)-, (2S-(2alpha(E),3beta,4beta,5alpha(2R*,3R*(1R*,2R*))))-

Registry Numbers

CAS Registry Number

  • 12650-69-0

FDA UNII

  • D0GX863OA5

Other Registry Number

  • 62916-63-6

System Generated Number

  • 0012650690

Structure Descriptors

InChI

1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1

InChIKey

MINDHVHHQZYEEK-HBBNESRFSA-N

Smiles

C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]2CO[C@@H](C\C(=C\C(=O)OCCCCCCCCC(=O)O)\C)[C@H](O)[C@@H]2O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 1638mg/kg (1638mg/kg)   United States Patent Document. Vol. #4206224,
mouse LD50 oral 5gm/kg (5000mg/kg)   United States Patent Document. Vol. #4206224,
mouse LD50 subcutaneous 4gm/kg (4000mg/kg)   United States Patent Document. Vol. #4206224,
rat LD50 intravenous 1310mg/kg (1310mg/kg)   United States Patent Document. Vol. #4206224,
rat LD50 oral 5gm/kg (5000mg/kg)   United States Patent Document. Vol. #4206224,
rat LD50 subcutaneous 5gm/kg (5000mg/kg)   United States Patent Document. Vol. #4206224,