3482-38-0

Usage

Uses

Used in Pharmaceutical Industry:
3,11-Diketofusidic acid is used as a key intermediate for the synthesis of Fusidic Acid, which is an important antibiotic. It is particularly effective against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). 3,11-diketofusidic acid contributes to the development of new treatments for bacterial infections and enhances the effectiveness of existing antibiotics.
Used in Research and Development:
In the field of scientific research, 3,11-diketofusidic acid is utilized as a valuable compound for studying the structure and function of Fusidic Acid and its derivatives. This helps researchers understand the mechanisms of action, resistance, and potential improvements in the design of new antibiotics.
Used in Drug Synthesis:
3,11-Diketofusidic acid is employed as a building block in the synthesis of various other pharmaceutical compounds, expanding its applications beyond just Fusidic Acid. Its versatility in chemical reactions allows for the creation of a diverse range of drugs with different therapeutic properties.

InChI:InChI=1/C31H44O6/c1-7-26(34)37-25-16-31(6)21-12-11-20-18(4)23(32)13-14-30(20,5)28(21)24(33)15-22(31)27(25)19(29(35)36)10-8-9-17(2)3/h9,18,20-22,25,28H,7-8,10-16H2,1-6H3,(H,35,36)/b27-19-/t18-,20?,21-,22-,25-,28-,30-,31+/m0/s1

Upstream product

• 3482-49-3 fusidine 

Relevant academic research and scientific papers

Structure-activity relationship analyses of fusidic acid derivatives highlight crucial role of the C-21 carboxylic acid moiety to its anti-mycobacterial activity

Fusidic acid (FA) is a potent congener of the fusidane triterpenoid class of antibiotics. Structure-activity relationship (SAR) studies suggest the chemical structure of FA is optimal for its antibacterial activity. SAR studies from our group within the context of a drug repositioning approach in tuberculosis (TB) suggest that, as with its antibacterial activity, the C-21 carboxylic acid group is indispensable for its anti-mycobacterial activity. Further studies have led to the identification of 16-deacetoxy-16β-ethoxyfusidic acid (58), an analog which exhibited comparable activity to FA with an in vitro MIC99 value of 0.8 μM. Preliminary SAR studies around the FA scaffold suggested that the hydrophobic side chain at C-20, like the C-11 OH group, was required for activity. The C-3 OH group, however, can be functionalized to obtain more potent compounds.

Synthesis of Fusidic Acid Derivatives Yields a Potent Antibiotic with an Improved Resistance Profile

Fusidic acid (FA) is a potent steroidal antibiotic that has been used in Europe for more than 60 years to treat a variety of infections caused by Gram-positive pathogens. Despite its clinical success, FA requires significantly elevated dosing (3 g on the first day, 1.2 g on subsequent days) to minimize resistance, as FA displays a high resistance frequency, and a large shift in minimum inhibitory concentration is observed for resistant bacteria. Despite efforts to improve on these aspects, all previously constructed derivatives of FA have worse antibacterial activity against Gram-positive bacteria than the parent natural product. Here, we report the creation of a novel FA analogue that has equivalent potency against clinical isolates of Staphylococcus aureus (S. aureus) and Enterococcus faecium (E. faecium) as well as an improved resistance profile in vitro when compared to FA. Importantly, this new compound displays efficacy against an FA-resistant strain of S. aureus in a soft-tissue murine infection model. This work delineates the structural features of FA necessary for potent antibiotic activity and demonstrates that the resistance profile can be improved for this scaffold and target.