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[ CAS No. 6990-06-3 ] Fusidine

Cat. No.: A127938
Chemical Structure| 6990-06-3
Chemical Structure| 6990-06-3
Structure of 6990-06-3 * Storage: Sealed in dry,2-8°C
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
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Product Citations

Samaneh Toufanian ; Jody Mohammed ; Erica Winterhelt , et al. DOI:

Abstract: Methicillin-resistant Staphylococcus aureus (MRSA) is associated with high levels of morbidity and is considered a difficult-to-treat infection, often requiring nonstandard treatment regimens and antibiotics. Since over 40% of the emerging antibiotic compounds have insufficient solubility that limits their bioavailability and thus efficacy through oral or intravenous administration, it is crucial that alternative drug delivery products be developed for wound care applications. Existing effective treatments for soft tissue MRSA infections, such as fusidic acid (FA), which is typically administered orally, could also benefit from alternative routes of administration to improve local efficacy and bioavailability while reducing the required therapeutic dose. Herein, we report an antimicrobial poly(oligoethylene glycol methacrylate) (POEGMA)-based composite hydrogel loaded with fusidic acid-encapsulating self-assembled polylactic acid-b-poly(oligo(ethylene glycol) methyl ether methacrylate) (PLA-POEGMA) nanoparticles for the treatment of MRSA-infected skin wounds. The inclusion of the self-assembled nanoparticles (380 nm diameter when loaded with fusidic acid) does not alter the favorable mechanical properties and stability of the hydrogel in the context of its use as a wound dressing, while fusidic acid (FA) can be released from the hydrogel over ∼10 h via a diffusion-controlled mechanism. The antimicrobial studies demonstrate a clear zone of inhibition in vitro and a 1−2 order of magnitude inhibition of bacterial growth in vivo in an MRSA-infected full-thickness excisional murine wound model even at very low antibiotic doses. Our approach thus can both circumvent challenges in the local delivery of hydrophobic antimicrobial compounds and directly deliver antimicrobials into the wound to effectively combat methicillin-resistant infections using a fraction of the drug dose required using other clinically relevant strategies.

Keywords: biomaterials ; wound care ; wound dressing ; antimicrobial resistance ; hydrogels ; self-assembled nanoparticles ; drug release kinetics ; copolymer

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Product Details of [ 6990-06-3 ]

CAS No. :6990-06-3 MDL No. :MFCD00865135
Formula : C31H48O6 Boiling Point : -
Linear Structure Formula :- InChI Key :IECPWNUMDGFDKC-MZJAQBGESA-N
M.W : 516.71 Pubchem ID :3000226
Synonyms :
Fusidate;SQ-16603;CEM-102;Fucidine;Fucidin;Anhydrous Fusidic Acid;Fusidic acid
Chemical Name :(Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyldodecahydro-1H-cyclopenta[a]phenanthren-17(2H,10H,14H)-ylidene)-6-methylhept-5-enoic acid

Calculated chemistry of [ 6990-06-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.81
Num. rotatable bonds : 6
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 146.33
TPSA : 104.06 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.6
Log Po/w (XLOGP3) : 5.51
Log Po/w (WLOGP) : 5.67
Log Po/w (MLOGP) : 4.14
Log Po/w (SILICOS-IT) : 4.72
Consensus Log Po/w : 4.73

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -6.12
Solubility : 0.000393 mg/ml ; 0.000000761 mol/l
Class : Poorly soluble
Log S (Ali) : -7.45
Solubility : 0.0000182 mg/ml ; 0.0000000351 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.3
Solubility : 0.0257 mg/ml ; 0.0000498 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 6.58

Safety of [ 6990-06-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P301+P312+P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:
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Sodium (Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyldodecahydro-1H-cyclopenta[a]phenanthren-17(2H,10H,14H)-ylidene)-6-methylhept-5-enoate

Reason: Free-salt

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