Fusidate sodium

Fusidate sodium

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Fusidate sodium
Category Antibiotics
Catalog number BBF-03944
CAS 751-94-0
Molecular Weight 538.70
Molecular Formula C31H47NaO6
Purity 98%

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Description

Sodium fusidate is a bacteriostatic antibiotic isolated from the fermentation broth of Fusidium coccineum. It suppresses nitric oxide lysis of pancreatic islet cells. It also inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA. It is also used to inhibit the replication of gram-positive bacteria including Staphylococcus, Streptococcus, and Corynebacterium species.

Specification

Related CAS 6990-06-3 (free acid)
Synonyms Fucidin; 16-Acetate (Z)-3α,11α,16β-Trihydroxy-29-Nor-8α,9β,13α,14β-dammara-17(20),24-dien-21-oic Acid Monosodium Salt; (3α,4α,8α,9β,11α,13α,14β,16β,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid Monosodium Salt; SQ 16360; ZN 6-Na
Shelf Life 2 month in rt, long time
Storage Store at -20°C
IUPAC Name sodium;(2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate
Canonical SMILES CC1C2CCC3(C(C2(CCC1O)C)C(CC4C3(CC(C4=C(CCC=C(C)C)C(=O)[O-])OC(=O)C)C)O)C.[Na+]
InChI InChI=1S/C31H48O6.Na/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32;/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36);/q;+1/p-1/b26-20-;/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-;/m0./s1
InChI Key HJHVQCXHVMGZNC-JCJNLNMISA-M
Source Fusidium coccineum

Properties

Appearance White Solid
Application Anti-Bacterial Agents
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 635.6°C at 760 mmHg
Melting Point >200°C (dec.)
Solubility Soluble in Water (50 mg/mL)

Reference Reading

1.Repurposing auranofin for the treatment of cutaneous staphylococcal infections.
Thangamani S1, Mohammad H1, Abushahba MF2, Sobreira TJ3, Seleem MN4. Int J Antimicrob Agents. 2016 Mar;47(3):195-201. doi: 10.1016/j.ijantimicag.2015.12.016. Epub 2016 Jan 23.
The scourge of multidrug-resistant bacterial infections necessitates the urgent development of novel antimicrobials to address this public health challenge. Drug repurposing is a proven strategy to discover new antimicrobial agents; given that these agents have undergone extensive toxicological and pharmacological analysis, repurposing is an effective method to reduce the time, cost and risk associated with traditional antibiotic innovation. In this study, the in vitro and in vivo antibacterial activities of an antirheumatic drug, auranofin, was investigated against multidrug-resistant Staphylococcus aureus. The results indicated that auranofin possesses potent antibacterial activity against all tested strains of S. aureus, including meticillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA), with minimum inhibitory concentrations (MICs) ranging from 0.0625μg/mL to 0.125μg/mL.
2.The Antimicrobial Agent Fusidic Acid Inhibits Organic Anion Transporting Polypeptide-Mediated Hepatic Clearance and May Potentiate Statin-Induced Myopathy.
Eng H1, Scialis RJ1, Rotter CJ1, Lin J1, Lazzaro S1, Varma MV1, Di L1, Feng B1, West M1, Kalgutkar AS2. Drug Metab Dispos. 2016 May;44(5):692-9. doi: 10.1124/dmd.115.067447. Epub 2016 Feb 17.
Chronic treatment of methicillin-resistantStaphylococcus aureusstrains with the bacteriostatic agent fusidic acid (FA) is frequently associated with myopathy including rhabdomyolysis upon coadministration with statins. Because adverse effects with statins are usually the result of drug-drug interactions, we evaluated the inhibitory effects of FA against human CYP3A4 and clinically relevant drug transporters such as organic anion transporting polypeptides OATP1B1 and OATP1B3, multidrug resistant protein 1, and breast cancer resistance protein, which are involved in the oral absorption and/or systemic clearance of statins including atorvastatin, rosuvastatin, and simvastatin. FA was a weak reversible (IC50= 295 ± 1.0μM) and time-dependent (KI= 216 ± 41μM andkinact= 0.0179 ± 0.001 min(-1)) inhibitor of CYP3A4-catalyzed midazolam-1'-hydroxylase activity in human liver microsomes. FA demonstrated inhibition of multidrug resistant protein 1-mediated digoxin transport with an IC50value of 157 ± 1.
3.Mechanism of fusidic acid inhibition of RRF- and EF-G-dependent splitting of the bacterial post-termination ribosome.
Borg A1, Pavlov M1, Ehrenberg M2. Nucleic Acids Res. 2016 Mar 21. pii: gkw178. [Epub ahead of print]
The antibiotic drug fusidic acid (FA) is commonly used in the clinic against gram-positive bacterial infections. FA targets ribosome-bound elongation factor G (EF-G), a translational GTPase that accelerates both messenger RNA (mRNA) translocation and ribosome recycling. How FA inhibits translocation was recently clarified, but FA inhibition of ribosome recycling by EF-G and ribosome recycling factor (RRF) has remained obscure. Here we use fast kinetics techniques to estimate mean times of ribosome splitting and the stoichiometry of GTP hydrolysis by EF-G at varying concentrations of FA, EF-G and RRF. These mean times together with previous data on uninhibited ribosome recycling were used to clarify the mechanism of FA inhibition of ribosome splitting. The biochemical data on FA inhibition of translocation and recycling were used to model the growth inhibitory effect of FA on bacterial populations. We conclude that FA inhibition of translocation provides the dominant cause of bacterial growth reduction, but that FA inhibition of ribosome recycling may contribute significantly to FA-induced expression of short regulatory open reading frames, like those involved in FA resistance.
4.Antimicrobial resistance of Staphylococcus aureus isolated from skin infections and its implications in various clinical conditions in Korea.
Baek YS1, Jeon J1, Ahn JW1, Song HJ1. Int J Dermatol. 2016 Apr;55(4):e191-7. doi: 10.1111/ijd.13046. Epub 2016 Feb 19.
BACKGROUND: Periodic investigations into patterns of antimicrobial resistance can help to optimize the efficacy of treatment and limit the development of resistance.

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