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Mupirocin

HCID 446596
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Grundinformationen

CAS
12650-69-0
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
Summenformel
C26H44O9
Durchschnittliche Molmasse
500,6 g/mol
Monoisotopische Masse
500,29853299

Überblick

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-).

Namen und Bezeichner

Bevorzugter 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
Englischer Name
Mupirocin
Summenformel
C26H44O9
Molmasse
500.62

Namen und Synonyme

Mupirocin12650-69-0Pseudomonic acidMupirocinePseudomonic acid ACentanyBactodermMupirocinaMupirocinumTurixintrans-Pseudomonic acidBRL 4910A
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
12650-69-0

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3
Polarare Oberfläche (TPSA)
146 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
17
Schwere Atome
35
Formalladung
0
Komplexität
694

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

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

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 Einträge

77-78

77 - 78 °C

Physical DescriptionSolid
Collision Cross Section · 2 Einträge

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]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

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

Toxikologische Informationen

Adverse EffectsAdverse Drug Reactions
Toxicity Summary · 1 Eintrag

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

Sicherheitsdaten

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 6 Einträge

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 Eintrag

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 Eintrag

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.

Zugehörige Reaktionen

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PubChem CID
446596
DTXSID
DTXSID0046438
ChEMBL
CHEMBL719
ChEBI
CHEBI:7025
UNII
D0GX863OA5
EC Number
603-145-3
Nikkaji
J15.623J

Physikochemische Eigenschaften

Schmelzpunkt
77 · 77-780C
Siedepunkt
672 ℃ · 672℃
Dichte
1.183 · 1.183±0.06 g/cm3(Predicted)
Flammpunkt
110 ° · >110°(230°F)
storage temp.
-20 °C · Inert atmosphere,Store in freezer, under -20°C
Löslichkeit
2 O: · H2O: 12 mg/mL, soluble
Aggregatzustand
solid
pka
4.78 · 4.78±0.10(Predicted)
Farbe
white to tan
Wasserlöslichkeit
Soluble in DMSO or methanol. Sparingly soluble in water
Merck
14 · 14,6302
Stabilität
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 Datenbank
12650 · 12650-69-0(CAS DataBase Reference)
wgk
2
hs_code
2941906000
RTECS-Nr.
RA6907000
Speicherklasse
11 - Combustible Solids
Metabolism/MetabolitesFollowing intravenous or oral administration, mupirocin undergoes rapid hepatic metabolism to form the principal metabolite monic acid, which has no antibacterial activity.
FDA Pharmacological Classification · 6 Einträge

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 · 2 Einträge

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 · 4 Einträge

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.

Cellular LocationsCytoplasm

Verwendung und Herstellung

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

Anwendungen

BeschreibungMupirocin (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.

VerwendenMupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Kieselsure (H4SiO4), Zinksalz (1:2), Mangan-dotiert
Ergänzende Hinweise · 1 Eintrag

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.