Drugbank Logo

Showing drug card for Mupirocin (DB00410)

Legend: drug field target field enzyme field

for drugs
Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:05:47
Primary Accession Number DB00410
Secondary Accession Number
  • APRD00162
Name Mupirocin
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.
Synonyms
  1. MRC
  2. Mupirocine
  3. Pseudomonic acid
  4. mupirocin
Brand Names
  1. Bactoderm
  2. Bactroban
  3. Bactroban Nasal
  4. Centany
  5. Turixin
Brand Mixtures Not Available
Chemical IUPAC Name 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
Chemical Formula C26H44O9
Chemical Structure Structure
CAS Registry Number 12650-69-0
InChI Identifier InChI=1/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/f/h28H
InChI Key MINDHVHHQZYEEK-GAUGRCCHDX
KEGG Drug D01076 Link Image
KEGG Compound C11758 Link Image
PubChem Compound 446596 Link Image
PubChem Substance 7848139 Link Image
ChEBI ID Not Available
PharmGKB ID PA450563 Link Image
HET ID MRC Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02239757 Link Image
RxList Link http://www.rxlist.com/cgi/generic/mupi.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Mupirocin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference B. B. Snider, G. Phillips, J. Am. Chem. Soc. 104, 1113 (1982)
Average Molecular Weight 500.6222
Monoisotopic Molecular Weight 500.2985
State Solid
Melting Point 77-78oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.65e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP 2.25 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.28 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O
Canonical SMILES CC(O)C(C)C1OC1CC1COC(CC(C)=CC(=O)OCCCCCCCCC(O)=O)C(O)C1O
Drug Category
  • Anti-Bacterial Agents
  • Antibiotics
  • Protein Synthesis Inhibitors
ATC Codes
AHFS Codes
  • 84:04.04
Indication For the treatment of Staphylococci nasal carriers.
Pharmacology Mupirocin, an antibiotic produced from Pseudomonas fluorescens, is structurally unrelated to any other topical or systemic antibiotics. Mupirocin is used to treat infection caused by Staphylococcus aureus and beta-hemolytic streptococci including Streptococcus pyogenes. This antibiotic has little, if any, potential for cross-resistance with other antibiotics.
Mechanism of Action Mupirocin reversibly binds to bacterial isoleucyl-tRNA synthetase, an enzyme which promotes the conversion of isoleucine and tRNA to isoleucyl-tRNA, resulting in the inhibition of bacterial protein and RNA synthesis.
Absorption No measurable systemic absorption
Toxicity Not Available
Protein Binding 97%
Biotransformation Hepatic. Following intravenous or oral administration, mupirocin is rapidly metabolized. The principal metabolite is monic acid, which has no antibacterial activity.
Half Life 20 to 40 minutes
Dosage Forms
Form Route
Cream Topical
Ointment Topical
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Isoleucyl-tRNA synthetase
Drug Target 1 [top]
Target 1 ID 892
Target 1 Name Isoleucyl-tRNA synthetase
Target 1 Synonyms
  1. EC 6.1.1.5
  2. IleRS
  3. Isoleucine--tRNA ligase
Target 1 Gene Name ileS
Target 1 Protein Sequence >Isoleucyl-tRNA synthetase 
MDYKETLLMPKTDFPMRGGLPNKEPQIQEKWDAEDQYHKALEKNKGNETFILHDGPPYAN
GNLHMGHALNKILKDFIVRYKTMQGFYAPYVPGWDTHGLPIEQALTKKGVDRKKMSTAEF
REKCKEFALEQIELQKKDFRRLGVRGDFNDPYITLKPEYEAAQIRIFGEMADKGLIYKGK
KPVYWSPSSESSLAEAEIEYHDKRSASIYVAFNVKDDKGVVDADAKFIIWTTTPWTIPSN
VAITVHPELKYGQYNVNGEKYIIAEALSDAVAEALDWDKASIKLEKEYTGKELEYVVAQH
PFLDRESLVINGDHVTTDAGTGCVHTAPGHGEDDYIVGQKYELPVISPIDDKGVFTEEGG
QFEGMFYDKANKAVTDLLTEKGALLKLDFITHSYPHDWRTKKPVIFRATPQWFASISKVR
QDILDAIENTNFKVNWGKTRIYNMVRDRGEWVISRQRVWGVPLPVFYAENGEIIMTKETV
NHVADLFAEHGSNIWFEREAKDLLPEGFTHPGSPNGTFTKETDIMDVWFDSGSSHRGVLE
TRPELSFPADMYLEGSDQYRGWFNSSITTSVATRGVSPYKFLLSHGFVMDGEGKKMSKSL
GNVIVPDQVVKQKGADIARLWVSSTDYLADVRISDEILKQTSDVYRKIRNTLRFMLGNIN
DFNPDTDSIPESELLEVDRYLLNRLREFTASTINNYENFDYLNIYQEVQNFINVELSNFY
LDYGKDILYIEQRDSHIRRSMQTVLYQILVDMTKLLAPILVHTAEEVWSHTPHVKEESVH
LADMPKVVEVDQALLDKWRTFMNLRDDVNRALETARNEKVIGKSLEAKVTIASNDKFNAS
EFLTSFDALHQLFIVSQVKVVDKLDDQATAYEHGDIVIEHADGEKCERCWNYSEDLGAVD
ELTHLCPRCQQVVKSLV
Target 1 Number of Residues 932
Target 1 Molecular Weight 104885
Target 1 Theoretical pI 5.17
Target 1 GO Classification
Function
ion binding
cation binding
transition metal ion binding
zinc ion binding
isoleucine-tRNA ligase activity
binding
nucleotide binding
purine nucleotide binding
adenyl nucleotide binding
ATP binding
catalytic activity
ligase activity
ligase activity, forming phosphoric ester bonds
RNA ligase activity
tRNA ligase activity
Process
isoleucyl-tRNA aminoacylation
physiological process
metabolism
cellular metabolism
nucleobase, nucleoside, nucleotide and nucleic acid metabolism
RNA metabolism
tRNA metabolism
tRNA aminoacylation
tRNA aminoacylation for protein translation
Component
Not Available
Target 1 General Function Translation, ribosomal structure and biogenesis
Target 1 Specific Function Catalyzes the attachment of isoleucine to tRNA(Ile). As IleRS can inadvertently accommodate and process structurally similar amino acids such as valine, to avoid such errors it has two additional distinct tRNA(Ile)-dependent editing activities. One activity is designated as 'pretransfer' editing and involves the hydrolysis of activated Val-AMP. The other activity is designated 'posttransfer' editing and involves deacylation of mischarged Val-tRNA(Ile)
Target 1 Pathways
Name SMPDB Link KEGG Link
Valine, leucine and isoleucine biosynthesis map00290 Link Image
Target 1 Reactions
  • ATP + L-isoleucine + tRNAIle = AMP + diphosphate + L-isoleucyl-tRNAIle
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 437916 Link Image
Target 1 UniProtKB/Swiss-Prot ID P41972 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name SYI1_STAAU Link Image
Target 1 PDB ID 1QU2 Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasm
Target 1 Gene Sequence >2754 bp 
ATGGATTACAAAGAAACGTTATTAATGCCTAAAACAGATTTCCCAATGCGAGGTGGTTTA
CCAAACAAGGAACCGCAAATTCAAGAAAAATGGGATGCAGAAGATCAATACCATAAAGCG
TTAGAAAAAAATAAAGGTAACGAAACATTCATTTTACATGATGGCCCACCATACGCGAAT
GGTAACTTACATATGGGACATGCCTTGAACAAAATTTTAAAAGACTTTATTGTACGTTAT
AAAACTATGCAAGGGTTCTATGCACCATACGTACCAGGTTGGGATACACATGGTTTGCCA
ATTGAACAAGCATTAACGAAAAAAGGTGTTGACCGTAAGAAAATGTCAACAGCTGAATTC
CGTGAGAAATGTAAAGAATTTGCTTTAGAACAAATTGAATTACAGAAAAAAGATTTTAGA
CGTTTAGGTGTTCGTGGTGACTTTAATGATCCATATATTACATTAAAACCTGAATACGAA
GCTGCACAAATTCGTATTTTTGGAGAAATGGCAGATAAAGGTTTAATTTATAAAGGTAAA
AAGCCAGTTTATTGGTCTCCTTCAAGTGAGTCTTCATTAGCAGAAGCAGAAATTGAATAT
CACGATAAACGTTCAGCATCAATTTACGTTGCATTTAACGTTAAAGATGACAAAGGTGTC
GTTGATGCAGATGCTAAATTTATTATCTGGACAACAACGCCATGGACAATTCCATCAAAT
GTTGCGATTACCGTTCATCCAGAATTAAAATACGGTCAATACAATGTAAATGGCGAAAAA
TATATTATTGCAGAAGCCTTATCTGACGCCGTAGCAGAAGCACTGGATTGGGATAAAGCA
TCAATCAAATTAGAAAAAGAATACACAGGTAAGGAATTGGAGTATGTTGTAGCACAACAT
CCATTCTTAGATAGAGAATCGTTAGTGATTAATGGTGATCATGTTACTACAGATGCTGGT
ACAGGTTGTGTACATACAGCACCAGGTCACGGGGAAGATGACTATATTGTTGGTCAAAAA
TATGAATTGCCAGTAATTAGTCCAATCGATGATAAAGGTGTATTTACTGAAGAAGGCGGC
CAATTTGAAGGAATGTTCTATGATAAAGCTAATAAAGCCGTTACTGATTTATTAACAGAA
AAAGGTGCACTATTAAAATTAGACTTTATTACACATAGCTATCCACACGACTGGAGAACA
AAAAAACCTGTAATTTTCCGTGCTACACCACAATGGTTTGCTTCAATCAGTAAAGTAAGA
CAAGATATTTTAGATGCAATCGAAAATACAAACTTCAAAGTAAATTGGGGTAAAACACGT
ATTTACAATATGGTTCGTGACCGTGGCGAATGGGTTATTTCTCGTCAACGTGTTTGGGGT
GTACCGTTACCAGTATTTTATGCTGAAAATGGCGAAATTATCATGACGAAAGAAACAGTG
AATCATGTTGCTGATTTATTTGCAGAACACGGTTCAAATATTTGGTTTGAAAGAGAAGCG
AAAGACTTACTACCAGAAGGATTTACACATCCAGGCAGCCCTAACGGTACATTTACTAAA
GAAACAGACATTATGGACGTTTGGTTTGATTCTGGTTCATCACACCGTGGCGTGTTGGAA
ACAAGACCGGAATTAAGTTTCCCAGCAGATATGTATTTAGAAGGTAGTGACCAATATCGT
GGTTGGTTCAACTCTTCTATTACAACTTCAGTTGCTACAAGAGGAGTATCACCTTATAAA
TTCTTACTTTCTCATGGTTTTGTTATGGACGGTGAAGGTAAGAAAATGAGTAAATCTTTA
GGTAATGTGATTGTACCTGACCAAGTGGTTAAACAAAAAGGTGCTGATATTGCGAGACTT
TGGGTAAGTAGTACGGACTATTTAGCTGATGTTAGAATTTCTGATGAAATTTTAAAACAA
ACATCTGATGTTTATCGTAAAATCAGAAATACATTAAGATTTATGTTAGGTAATATTAAT
GATTTCAATCCTGATACAGATAGCATTCCTGAATCAGAGTTATTAGAAGTTGATCGTTAC
TTGCTAAATCGTTTACGTGAATTTACTGCAAGTACGATTAACAACTATGAAAACTTTGAC
TACTTAAATATTTATCAAGAAGTTCAAAACTTTATCAATGTTGAGTTAAGTAATTTCTAT
TTGGATTACGGTAAAGATATTTTATATATTGAACAACGTGATTCTCATATCCGTCGTAGT
ATGCAAACAGTGTTATATCAAATTTTAGTTGATATGACGAAGTTGTTAGCACCAATCTTA
GTGCATACAGCTGAAGAAGTTTGGTCTCATACACCACATGTTAAAGAAGAAAGTGTTCAC
TTAGCAGACATGCCTAAAGTTGTAGAAGTAGATCAAGCTTTATTGGATAAATGGCGTACA
TTTATGAATTTACGTGATGATGTGAACCGTGCATTAGAAACTGCTCGTAATGAAAAAGTT
ATTGGTAAATCATTAGAAGCTAAAGTTACGATTGCTAGTAACGATAAATTTAATGCATCT
GAATTCTTAACTTCATTTGATGCATTACATCAATTATTTATCGTGTCACAAGTTAAAGTT
GTAGATAAGTTAGATGATCAGGCAACAGCTTATGAACATGGTGATATTGTCATCGAACAT
GCAGATGGTGAAAAATGTGAAAGATGTTGGAACTATTCAGAGGATCTTGGTGCTGTTGAT
GAATTGACGCATCTATGCCCACGATGCCAACAAGTTGTAAAATCACTTGTATAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Silvian LF, Wang J, Steitz TA: Insights into editing from an ile-tRNA synthetase structure with tRNAile and mupirocin. Science. 1999 Aug 13;285(5430):1074-7. [PubMed Link Image]
  2. Chalker AF, Ward JM, Fosberry AP, Hodgson JE: Analysis and toxic overexpression in Escherichia coli of a staphylococcal gene encoding isoleucyl-tRNA synthetase. Gene. 1994 Apr 8;141(1):103-8. [PubMed Link Image]
Target 1 Drug References
  1. Thomas DG, Wilson JM, Day MJ, Russell AD: Mupirocin resistance in staphylococci: development and transfer of isoleucyl-tRNA synthetase-mediated resistance in vitro. J Appl Microbiol. 1999 Apr;86(4):715-22. [PubMed Link Image]
  2. Antonio M, McFerran N, Pallen MJ: Mutations affecting the Rossman fold of isoleucyl-tRNA synthetase are correlated with low-level mupirocin resistance in Staphylococcus aureus. Antimicrob Agents Chemother. 2002 Feb;46(2):438-42. [PubMed Link Image]
  3. Hurdle JG, O'Neill AJ, Chopra I: The isoleucyl-tRNA synthetase mutation V588F conferring mupirocin resistance in glycopeptide-intermediate Staphylococcus aureus is not associated with a significant fitness burden. J Antimicrob Chemother. 2004 Jan;53(1):102-4. Epub 2003 Dec 4. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.