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F0756

Sigma-Aldrich

Fusidic acid

Synonym(s):

Ramycin

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About This Item

Empirical Formula (Hill Notation):
C31H48O6
CAS Number:
6990-06-3
Molecular Weight:
516.71
EC Number:
230-256-0
MDL number:
MFCD00865135
UNSPSC Code:
12352106
PubChem Substance ID:
57654174
NACRES:
NA.77

Quality Level

200

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@@]3(C)[C@@]([H])([C@H](O)C[C@@]4([H])\C([C@H](C[C@]34C)OC(C)=O)=C(/CC\C=C(\C)C)C(O)=O)[C@@]1(C)CC[C@@H](O)[C@H]2C

InChI

1S/C31H48O6/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)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1

InChI key

IECPWNUMDGFDKC-MZJAQBGESA-N

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Application

Fusidic acid has been used:
  • as a standard in thin-layer chromatography (TLC)-densitometric method
  • to study its ability to bind to human serum albumin
  • as an antibiotic in combination with tannic acid to determine minimum inhibitory concentrations (MIC) in methicillin-resistant Staphylococcus aureus (MRSA)

Biochem/physiol Actions

Fusidic acid is a tetracyclic triterpenoid with antibiotic activity against Gram-positive bacteria. It is derived from Fusidium coccineum. It shows its activity against anaerobes, corynebacterial, Nocardia, and Neisseria species. Fusidic acid exhibits therapeutic effects against Staphylococcal infections, skin infections.
Suppresses nitric oxide lysis of pancreatic islet cells. Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jade Bojkovic et al.
Journal of bacteriology, 198(4), 731-741 (2015-12-17)
Lipid A on the Gram-negative outer membrane (OM) is synthesized in the cytoplasm by the Lpx pathway and translocated to the OM by the Lpt pathway. Some Acinetobacter baumannii strains can tolerate the complete loss of lipopolysaccharide (LPS) resulting from
Tannic acid as phytochemical potentiator for antibiotic resistance adaptation
Myint K, et al.
APCBEE procedia, 7, 175-181 (2013)
Silke Besier et al.
Molecular microbiology, 47(2), 463-469 (2003-01-10)
Fusidic acid is a potent antibiotic against severe Gram-positive infections that interferes with the function of elongation factor G (EF-G), thereby leading to the inhibition of bacterial protein synthesis. In this study, we demonstrate that fusidic acid resistance in Staphylococcus
Christine Oswald et al.
Nature communications, 7, 13819-13819 (2016-12-17)
The deployment of multidrug efflux pumps is a powerful defence mechanism for Gram-negative bacterial cells when exposed to antimicrobial agents. The major multidrug efflux transport system in Escherichia coli, AcrAB-TolC, is a tripartite system using the proton-motive force as an
T N Peel et al.
Antimicrobial agents and chemotherapy, 57(1), 350-355 (2012-11-02)
The management of prosthetic joint infections remains a clinical challenge, particularly infections due to methicillin-resistant staphylococci. Previously, this infection was considered a contraindication to debridement and retention strategies. This retrospective cohort study examined the treatment and outcomes of patients with
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