Basic information
- Standard SMILES
C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O- InChIKey
MINDHVHHQZYEEK-HBBNESRFSA-N- Molecular formula
- C26H44O9
- Average molar mass
- 500.6 g/mol
- Monoisotopic mass
- 500.29853299
Overview
Mupirocin is an alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections. It has a role as an antibacterial drug, a protein synthesis inhibitor and a bacterial metabolite. It is a monocarboxylic acid, a triol, an epoxide, a secondary alcohol, a member of oxanes and an alpha,beta-unsaturated carboxylic ester. It is a conjugate acid of a mupirocin(1-).
Names & identifiers
- Preferred name
- Mupirocin
- IUPAC
- 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
- English name
- Mupirocin
- Molecular formula
- C26H44O9
- Molecular weight
- 500.62
Names & synonyms
Show more names
Database identifiers
- CAS
12650-69-0- PubChem CID
- 446596
- DTXSID
DTXSID0046438- ChEMBL
CHEMBL719- ChEBI
CHEBI:7025- UNII
- D0GX863OA5
- EC Number
- 603-145-3
- Nikkaji
- J15.623J
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 146 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 17
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 694
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents, Local; Antibacterial Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Dermatological medicines > Anti-infective medicines
Melting Point
77-78
77 - 78 °C
Collision Cross Section
215.12 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
214.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 77 · 77-780C
- Boiling point
- 672 ℃ · 672℃
- alpha
- 20 · D20 -19.3° (c = 1 in methanol)
- Density
- 1.183 · 1.183±0.06 g/cm3(Predicted)
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 2 O: · H2O: 12 mg/mL, soluble
- form
- solid
- pka
- 4.78 · 4.78±0.10(Predicted)
- color
- white to tan
- optical activity
- -15.7 to · [α]/D -15.7 to -20°, c = 1 in methanol
- Water Solubility
- Soluble in DMSO or methanol. Sparingly soluble in water
- λmax
- 222 nm · 222nm(EtOH)(lit.)
- Merck
- 14 · 14,6302
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- Major Application
- pharmaceutical
- InChIKey
- MINDHVHHQZYEEK-HBBNESRFSA-N
- SMILES
- [H][C@@]1(CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O)C[C@@H]2O[C@@]2([H])[C@@H](C)[C@H](C)O
- CAS DataBase Reference
- 12650 · 12650-69-0(CAS DataBase Reference)
- FDA UNII
- 0 GX863OA5 · D0GX863OA5
- ATC code
- 6 AX09,R01AX06 · D06AX09,R01AX06
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317
- Precautionary statements
- 261 · P261-P280
- WGK Germany
- 2 · 2
- RTECS
- 6907000 · RA6907000
- HS Code
- 2941906000 · 2941906000
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.
Warning
H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Toxicity Summary
Currently, no available study or report suggests that using topical mupirocin consistently causes systemic toxicity. As previously stated, caution is advised in individuals with severe renal impairment and those with large open wounds due to the potential for increased absorption and nephrotoxicity. In such cases, renal function should be closely monitored with scheduled renal function panels, as stated in the FDA guidelines for Bactroban.
Safety data
- wgk
- 2
- rtecs
- RA6907000
- hs_code
- 2941906000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Precautionary statements
- P261-P280
Chemistry & industry
Pharmacology
ATC Code
D06AX09
R - Respiratory system
D - Dermatologicals
QD - Dermatologicals
QR - Respiratory system
D06AX09
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_. 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). 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. 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. Mupirocin resistance as high as 81% has been reported previously. 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.
Mechanism of Action
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. 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.
FDA Pharmacological Classification
D0GX863OA5
MUPIROCIN
Established Pharmacologic Class [EPC] - RNA Synthetase Inhibitor Antibacterial
Mechanisms of Action [MoA] - RNA Synthetase Inhibitors
Mupirocin is a RNA Synthetase Inhibitor Antibacterial. The mechanism of action of mupirocin is as a RNA Synthetase Inhibitor.
MUPIROCIN
MeSH Pharmacological Classification
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Systemic or percutaneous absorption of mupirocin following dermal application is expected to be minimal in adults and children. Occlusive dressings do not significantly enhance drug absorption, but damaged skin may allow enhanced penetration of the drug across the skin barrier.
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.
No information available.
No information available.
Uses & manufacturing
Applications
UsesTopical antibiotics. This product is generally used for the inflammation of the skin, eczema, etc., or made into mupirocin ointment in the market.By reversibly binding to isoleucine transfer RNA synthetase, this product can prevent isoleucine incorporated so that the synthesis of all proteins in cells containing isoleucine can be stopped. Mupirocin has a unique mode of action. The epoxide-containing monic acid tail of the molecule is an analog of isoleucine and, as such, is a competitive inhibitor of isoleucyltRNA synthetase in bacterial cells. The corresponding mammalian enzyme is unaffected.
DescriptionMupirocin (pseudomonic acid A) is an antibiotic produced by Pseudomonas fluorescens. It is useful in the treatment of dermal infections, especially those involving S. aureus and S. epidermidis.
Usesantibacterial, antimycoplasmal, isoleucyl-tRNA synthetase inhibitor
UsesMupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.
UsesPseudomonic acid is a potent antibiotic produced by Pseudomonas fluorescens, reported by Fuller et al. in 1971. Pseudomonic acid has broad spectrum activity against Gram positive bacteria and was approved for topical human use in 1985. Pseudomonic acid acts as a potent and selective inhibitor of isoleucyl-tRNA synthetase.
UsesAn antibiotic inhibitor of isoleucyl-tRNA synthetase
Usesvasodilator
General DescriptionMupirocin (pseudomonic acid A, Bactroban) is the majorcomponent of a family of structurally related antibiotics,pseudomonic acids A to D, produced by the submergedfermentation of Pseudomonas fluorescens. Although theantimicrobial properties of P. fluorescens were recordedas early as 1887, it was not until 1971 that Fuller et al.identified the metabolites responsible for this activity. Thestructure of the major and most potent metabolite,pseudomonic acid A (which represents 90%–95% of the activefraction from P. fluorescens), was later confirmed bychemical synthesis to be the 9-hydroxynonanoic acidester of monic acid.The use of mupirocin is confined to external applications.280 Systemic administration of the antibiotic resultsin rapid hydrolysis by esterases to monic acid, which is inactivein vivo because of its inability to penetrate bacteria.Mupirocin has been used for the topical treatment ofimpetigo, eczema, and folliculitis secondarily infected bysusceptible bacteria, especially staphylococci and -hemolyticstreptococci. The spectrum of antibacterial activityof mupirocin is confined to Gram-positive and Gramnegativecocci, including staphylococci, streptococci,Neisseria spp., and M. catarrhalis. The activity of the antibioticagainst most Gram-negative and Gram-positivebacilli is generally poor, with the exception of H. influenzae.It is not effective against enterococci or anaerobicbacteria.Mupirocin interferes with RNA synthesis and protein synthesisin susceptible bacteria. It specifically and reversiblybinds with bacterial isoleucyl tRNA synthase to preventthe incorporation of isoleucine into bacterial proteins.282High-level, plasmid-mediated mupirocin resistance in S. aureushas been attributed to the elaboration of a modifiedisoleucyl tRNA that does not bind mupirocin.283 Inherent resistancein bacilli is likely because of poor cellular penetrationof the antibiotic.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2 -pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydro ybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.
Related reactions
Linked notes
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