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Mupirocin

CAT: 0013-GTR19164137-05Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19164137-05Size:50 mg
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Description
Mupirocin (BRL-4910A) is an antibiotic of the monoxycarbolic acid class; effective against Gram-positive bacteria, including MRSA. (In Vitro) :Mupirocin (BRL-4910A, Pseudomonic acid) (0-100 μM; 48 h) shows antibacterial effect against staphylococci, streptococci and certain gram-negative bacteria, with MIC values range from 0.06-0.25 μg/mL (MIC50 =0.12 μg/mL, MIC90 =0.25 μg/mL) .Mupirocin is highly bound (95% bound) to human serum protein, thus results in activity inhibition in the presence of human serum.Mupirocin apparently exerts its antimicrobial activity by reversibly inhibiting isoleucyl-transfer RNA, thereby inhibiting bacterial protein and RNA synthesis.Mupirocin (2% ointment) reduces pro-inflammatory cytokines IL-1β and IL-17 level, decreases tumor necrosis factor-alpha (TNF-α) expression, and increases the leavel of vascular endothelial growth factor (VEGF) .Mupirocin inhibits MS (S. epidermidis ATCC 12228), MR (S. epidermidis (Se56-99) ), and VIR (S. epidermidis (Se43-98) ) with MICs of 0.25, 1.26, 1.59 mg/L. (In Vivo) :MRSA: Meticillin-resistant Staphylococcus aureusMupirocin (BRL-4910A, Pseudomonic acid) is well absorbed after oral and parenteral administration but serum antibiotic concentrations were short-lived as a result of extensive degradation to the antibacterially inactive metabolite, monic acid A.Mupirocin (2% ointment; external administration; twice daily; 3-6 d) decreases the total bacterial loads in the skin lesions with either topical treatment.Mupirocin (2% ointment; external administration; 4 d) alleviates MRSA-infected pressure ulcers in mice.Mupirocin (100 mg/mL; s.c.; 7 d) exerts prevention efficacy against vascular prosthetic graft infection due to Staphylococcus epidermidis.
CAS Number
12650-69-0
Product Name Alternative
BRL 4910A
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
Ethanol: 100 mg/mL (199.75 mM) ; Water: 46 mg/mL warmed (91.88 mM) ; DMSO: 100 mg/mL warmed (199.75 mM)
Smiles
O=C (O) CCCCCCCCOC (/C=C (C) /C[C@@H]1OC[C@H] (C[C@@H]2O[C@H]2[C@H] ([C@@H] (O) C) C) [C@@H] (O) [C@H]1O) =O
Molecular Formula
C26H44O9
Molecular Weight
500.64
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
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 Information

Mupirocin

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-).

CAS Number12650-69-0
PubChem CID446596
IUPAC Name9-[(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
Molecular FormulaC26H44O9
Molecular Weight500.6
XLogP3
Topological Polar Surface Area146
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count17
Heavy Atom Count35
Formal Charge0
Complexity694
SMILES
C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O
InChI
InChI=1S/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
InChIKey
MINDHVHHQZYEEK-HBBNESRFSA-N
Chemical Structure
2D Structure
2D structure of Mupirocin
CAS: 12650-69-0
CID: 446596
Formula: C26H44O9
MW: 500.6
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight500.6
XLogP33
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count17
Exact Mass500.29853298
Monoisotopic Mass500.29853298
Topological Polar Surface Area146 Ų
Heavy Atom Count35
Formal Charge0
Complexity694
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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