Mupirocin

HCID 446596CAS 12650-69-0

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

Mupirocin12650-69-0Pseudomonic acidMupirocinePseudomonic acid ACentanyBactodermMupirocinaMupirocinumTurixintrans-Pseudomonic acidBRL 4910A
Show more names
MUPIROCIN CALCIUM231-791-2bactrobanL-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-(2S,3S)-3-(1S,2S)-2-hydroxy-1-methylpropyloxiranylmethyl-3-methyl-, 8-carboxyoctyl ester, (2E)-TurixiMupricin
BRL-4910A9-[(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 acidDTXSID0046438NSC-759182D0GX863OA5L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)-CHEBI:7025DTXCID8026438

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

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Solubility2.65e-02 g/L
Human Drugs · 4 items

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

Animal DrugsActive Ingredients (Mupirocin) -> FDA Greenbook
Melting Point · 2 items

77-78

77 - 78 °C

Physical DescriptionSolid

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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

Regulatory InformationMupirocin: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (25%)

Toxicology

Adverse EffectsAdverse Drug Reactions
Toxicity Summary · 1 item

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.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
2
rtecs
RA6907000
hs_code
2941906000
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

ATC Code · 6 items

D06AX09

R - Respiratory system

D - Dermatologicals

QD - Dermatologicals

QR - Respiratory system

D06AX09

Protein BindingThe protein binding of mupirocin is reported to be over 95%.
Pharmacodynamics · 1 item

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 · 1 item

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.

Biological Half-LifeIn 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.
Metabolism/MetabolitesFollowing intravenous or oral administration, mupirocin undergoes rapid hepatic metabolism to form the principal metabolite monic acid, which has no antibacterial activity.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >50
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Applications · 8 items

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

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Additional notes · 1 item

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

16 records

Linked notes

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