General
Preferred name
MUPIROCIN
Synonyms
Pseudomonic Acid ()
BRL-4910A ()
Mupirocin calcium hydrate ()
MUPIROCIN CALCIUM ()
Bactroban ()
BRL-4910A,Pseudomonic acid ()
pseudomonic acid A ()
Centany ()
Turixin ()
NSC-759182 ()
Trans-pseudomonic acid ()
Bactoderm ()
BRL 4910A ()
Mupirocin ()
BRL-4910F ()
Calcium pseudomonate ()
Calcium mupirocin dihydrate ()
Mupirocin calcium hydrate ()
Mupirocin calcium anhydrous ()
Mupirocin calcium dihydrate ()
Calcium mupirocin ()
BRL 4910F ()
P&D ID
PD000326
CAS
115074-43-6
104486-81-9
12650-69-0
Tags
natural product
drug
available
Approved by
FDA
First approval
1987
1995
Drug Status
investigational
approved
vet_approved
Drug indication
Bacterial infection
Antibacterial (topical)
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
METABOLISM
Following intravenous or oral administration, mupirocin undergoes rapid hepatic metabolism to form the principal metabolite monic acid, which has no antibacterial activity.[label]
MOA
Mupirocin specifically and reversibly binds to bacterial isoleucyl transfer-RNA (tRNA) synthetase, which is an enzyme that promotes the conversion of isoleucine and tRNA to isoleucyl-tRNA. Inhibition of this enzyme subsequently leads to the inhibition of the bacterial protein and RNA synthesis.[A178531] Mupirocin is bacteriostatic at lower concentrations but it exerts bactericidal effects with prolonged exposure, killing 90-99% of susceptible bacteria over a 24 hour period.[A178552]
INDICATION
Indicated for the treatment of impetigo and secondary skin infections, leading to traumatic skin lesions, due to _Staphylococcus aureus_ and _Streptococcus pyogenes_.[label]
ROE
Any mupirocin reaching the systemic circulation is rapidly metabolized to form the inactive monic acid, which is eliminated by renal excretion. Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin.[label]
TOXICITY
**LD50 and Nonclinical Toxicity**; ; The oral LD50 value in rats is 5000 mg/kg.[MSDS] Studies evaluating the carcinogenic potential of mupirocin have not been performed. In various _in vivo_ animal and _in vitro_ bacterial assays, there was no evidence of genotoxicity caused by mupirocin.[label] In reproduction studies using male and female rats, there were no signs of impaired fertility upon subcutaneous administration of mupirocin.[label]; ; **Use in special populations**; ; Mupirocin was found to be excreted in human milk. As there is limited data on the use of topical mupirocin in pregnant women, the use of this drug in these patients should be undertaken with caution. Based on the findings in clinical trials, topical mupirocin was shown to be safe and effective in pediatric patients aged 2 months to 16 years.
HALF-LIFE
In healthy male volunteers, the elimination half-life of mupirocin was about 20 to 40 minutes following intravenous administration. The elimination half-life of monic acid was about 30 to 80 minutes.[L6349]
ABSORPTION
Systemic or percutaneous absorption of mupirocin following dermal application is expected to be minimal in adults and children.[label] Occlusive dressings do not significantly enhance drug absorption, but damaged skin may allow enhanced penetration of the drug across the skin barrier.[A178552]
PHARMACODYNAMICS
Mupirocin is reported to be active against susceptible aerobic gram-positive cocci, such as _Staphylococcus aureus_, _Staphylococcus epidermidis_, and other beta-hemolytic streptococci_Streptococcus pyogenes_.[A178594] It mediates its antibacterial activity by inhibiting the bacterial protein synthesis and formation of bacterial proteins essential for survival. The minimum bactericidal concentration (MBC) against relevant pathogens is generally eight-fold to thirty-fold higher than the minimum inhibitory concentration (MIC).[label] In one clinical study investigating the therapeutic effectiveness of topical mupirocin in impetigo, the therapeutic response rate was about 94 to 98% after one week following the end of therapy.[label] In clinical studies of patients with primary and secondary skin infections, both elimination of the bacterial pathogen and clinical cure or improvement hav been demonstrated in over 90% of patients receiving topical mupirocin.[A178591] Mupirocin resistance as high as 81% has been reported previously.[A178600] Resistance to mupirocin, which occurs more frequently in methicillin-resistant than methicillin-susceptible staphylococci, may occur with the production of a modified isoleucyl-tRNA synthetase, or the acquisition of, by genetic transfer, a plasmid mediating a new isoleucyl-tRNA synthetase.[label]
DESCRIPTION
Mupirocin was initially isolated from Pseudomonas fluorescens . It is an unsaturated ester of 9-hydroxynonanoic acid. Functionally, it binds to bacterial isoleucyl-tRNA synthetase and disrupts isoleucine incorporation into bacterial proteins. This is a unique mechanism of action.
Isoleucine utilization has also been shown to be an essential pathway in P. falciparum and a potential target for antimalarial drug discovery . The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY. (GtoPdb)
Isoleucine utilization has also been shown to be an essential pathway in P. falciparum and a potential target for antimalarial drug discovery . The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY. (GtoPdb)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
1
Compound Sets
25
AdooQ Bioactive Compound Library
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
MedChem Express Bioactive Compound Library
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
NIH Clinical Collections (NCC)
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
77
Molecular Weight
500.3
Hydrogen Bond Acceptors
8
Hydrogen Bond Donors
4
Rotatable Bonds
16
Ring Count
2
Aromatic Ring Count
0
cLogP
2.59
TPSA
146.05
Fraction CSP3
0.85
Chiral centers
8.0
Largest ring
6.0
QED
0.11
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
DNA Damage/DNA Repair
Anti-infection
Target
DNA synthesis
antibiotic
Bacterial
DNA/RNA Synthesis
Antibiotics,Bacterial
Indication
impetigo
MOA
isoleucyl-tRNA synthetase inhibitor
Biosynthetic Origin
Polyketide
Therapeutic Indication
Antibacterial
Therapeutic Class
Antimicrobial
Antibiotics
Source data
