Isepamicin sulfate
[CAS# 67814-76-0]

Identification

• Classification: API >> Antibiotics >> Aminoglycoside
• Name: Isepamicin sulfate
• Synonyms: (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-2-[(2R,3R,4R,5S)-3,5-dihydroxy-5-methyl-4-methylamino-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-propanamide sulfate
• Molecular Formula: C₂₂H₄₃N₅O₁₂^.H₂SO₄
• Molecular Weight: 667.68
• CAS Registry Number: 67814-76-0
• SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O.OS(=O)(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+351+338-P302+352

Discovory and Applicatios

Isepamicin sulfate is an aminoglycoside antibiotic that was developed as a derivative of amikacin in the late 20th century. It was introduced to address the growing problem of resistance to older aminoglycosides and to provide a treatment option for infections caused by multi-drug resistant bacteria. Isepamicin is primarily used for the treatment of serious infections caused by Gram-negative bacteria, particularly in patients with compromised immune systems. It is especially effective against infections caused by Pseudomonas aeruginosa and various Enterobacteriaceae species, including Escherichia coli and Klebsiella pneumoniae.

The discovery of isepamicin sulfate was driven by the need for new antibiotics with improved activity against resistant bacterial strains. By modifying the chemical structure of amikacin, which itself is a derivative of kanamycin, researchers created isepamicin to enhance its effectiveness against a wider range of bacteria, particularly those resistant to other aminoglycosides. The modification of the sugar moiety in the molecular structure of isepamicin allows it to evade some of the common bacterial mechanisms of resistance, such as enzymatic modification by acetyltransferases, which would typically inactivate other aminoglycosides. This improvement in resistance profiles makes isepamicin a valuable option in treating infections that do not respond to conventional antibiotics.

Isepamicin sulfate works by binding to bacterial ribosomes, specifically the 30S subunit, thereby inhibiting protein synthesis. This action prevents bacteria from producing the proteins necessary for their growth and survival, ultimately leading to bacterial cell death. The drug is typically administered intravenously in hospital settings due to its potent activity and the need for careful monitoring during treatment. It is mainly used for the treatment of severe systemic infections, including pneumonia, sepsis, urinary tract infections, and infections in immunocompromised patients. It is particularly useful in treating infections caused by resistant pathogens in patients who have not responded to other antibiotics.

Like other aminoglycosides, isepamicin sulfate is known for its potential nephrotoxicity and ototoxicity, making careful dosing and monitoring of kidney and hearing function critical during treatment. Despite these risks, isepamicin remains a key antibiotic in hospitals, particularly in intensive care units, where patients are at high risk for infections caused by resistant bacteria. It is often used when first-line antibiotics fail or when there is a need for broad-spectrum coverage in critically ill patients.

Research into the optimization of isepamicin’s use continues, with a focus on minimizing side effects while maintaining its potent antibacterial activity. This includes the development of dosing regimens that reduce the risk of kidney damage and investigations into alternative delivery methods, such as liposomal formulations, to target bacterial cells more efficiently and reduce systemic exposure.

In conclusion, isepamicin sulfate is an important antibiotic that plays a crucial role in the treatment of severe infections caused by resistant bacteria. Its development as a more effective alternative to amikacin has improved therapeutic options for clinicians in the management of multi-drug resistant infections. Continued research into optimizing its use will ensure that isepamicin remains a valuable tool in the fight against antibiotic-resistant pathogens.