Gentamicinsulfate salt

Base Information

• Chemical Name: Gentamicinsulfate salt
• CAS No.: 1403-66-3
• Molecular Formula: C21H43N5O7
• Molecular Weight: 477.60
• Hs Code.: 3004909090
• ChEMBL ID: CHEMBL3039597
• Wikidata: Q105182996
• Mol file: 1403-66-3.mol

Synonyms:SCH-9724;Gentamicinsulfate salt;CHEMBL3039597;BDBM50476074;G-2419;Gentamycin, Antibiotic for Culture Media Use Only

Chemical Property of Gentamicinsulfate salt

Chemical Property:

• Appearance/Colour: clear amber liquid.
• Vapor Pressure: 8.85E-21mmHg at 25°C
• Melting Point: 102-108°
• Boiling Point: 669.4 °C at 760 mmHg
• PKA: pKa 8.2(66% DMF) (Uncertain);7.9(H2O) (Uncertain)
• Flash Point: 358.6 °C
• PSA: 627.17000
• Density: 1.3 g/cm³
• LogP: -1.62550
• Hydrogen Bond Donor Count: 24
• Hydrogen Bond Acceptor Count: 36
• Rotatable Bond Count: 19
• Exact Mass: 1389.90179599
• Heavy Atom Count: 96
• Complexity: 1850

Purity/Quality:

99% ^*data from raw suppliers

Gentamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)N.CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC.CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CN)N)N)N)O
• Isomeric SMILES: CC([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)N.CC([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)NC.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](CC[C@H](O3)CN)N)N)N)O
• Description: Gentamicin is a mixture of several antibiotic components produced by fermentation of Mi cromonospora purpurea and other related soil microorganisms (hence its name is spelled with an “i” instead of a “ y”). Gentamicins C-1, C-2, and C-1a are most prominent. Gentamicin is the most important of the aminoglycoside antibiotics still in use. Gentamicin was, for example, one of the first antibiotics to have significant activity against Pseudomonas aeruginosa infections. This water-loving, opportunistic pathogen frequently is encountered in burns, pneumonias, and urinary tract infections.
• Uses: antibacterial
• Indications: This antibiotic is a combination of three related aminoglycoside agents obtained from cultures of Micromonospora purpurea and acts by interfering with the bacterial synthesis of protein. It prevents bacterial protein synthesis by irreversibly binding to 30S ribosomal subunits. Its antibiotic spectrum is similar to that of neomycin, and cross-resistance does occur. Gentamicin is active against gram-negative organisms including Escherichia coli and a high percentage of strains of Pseudomonas species and other gram-negative bacteria. Proteus organisms show a variable degree of sensitivity. Some gram-positive organisms, including S. aureus and group A β-hemolytic streptococci, are also affected. In general, higher concentrations are needed to inhibit streptococci than those needed to inhibit staphylococci and many gram-negative bacteria. It is inactive against fungi, viruses, and most anaerobic bacteria. The most important use of gentamicin is in the treatment of systemic gram-negative infections, particularly those due to Pseudomonas organisms. Widespread use is unwarranted not only because equally effective drugs are available but also because of the risk of increasing the background of gentamicin-resistant organisms. Allergic reactions to gentamicin are unusual but may occur with prolonged use. Cross-reactivity with neomycin may occur.
• Therapeutic Function: Antibacterial
• Clinical Use: In severe sepsis of unknown origin, gentamicin has been traditionally combined with other agents. However, monotherapy has been shown to be as effective as combination therapy. In systemic Ps. aeruginosa infections it is advisable to combine gentamicin with an antipseudomonal penicillin or cephalosporin, owing to likelihood of gentamicin resistance. Suspected or documented Gram-negative septicemia, particularly when shock or hypotension is present Enterococcal endocarditis (with a penicillin) Respiratory tract infection caused by Gram-negative bacilli Urinary tract infection Bone and soft-tissue infections, including peritonitis, burns complicated by sepsis and infected surgical and traumatic wounds Serious staphylococcal infection when other conventional antimicrobial therapy is inappropriate Gentamicin drops are used for conjunctival infections and for infections of the external ear. The drug is also used in orthopedic surgery in bone cements. In these applications systemic concentrations achieved are negligible and toxicities are restricted to local effects. In the elderly and those with renal impairment the dosage must be suitably modified.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of nephrotoxicity with colistimethate or polymyxins and possibly cephalosporins; increased risk of ototoxicity and nephrotoxicity with capreomycin or vancomycin. Ciclosporin: increased risk of nephrotoxicity. Cytotoxics: increased risk of nephrotoxicity and possibly of ototoxicity with platinum compounds. Diuretics: increased risk of ototoxicity with loop diuretics. Muscle relaxants: effects of non-depolarising muscle relaxants and suxamethonium enhanced. Parasympathomimetics: antagonism of effect of neostigmine and pyridostigmine. Tacrolimus: increased risk of nephrotoxicity.

Refernces

Biotransformation of sisomicin and verdamicin by Micromonospora sagamiensis

10.1080/00021369.1982.10865090

The research investigates the biotransformation of sisomicin and verdamicin by Micromonospora sagamiensis. The study found that the resting cells of a 2-deoxystreptamine idiotrophic mutant of M. sagamiensis could transform sisomicin into gentamicin CIa and sagamicin, while verdamicin was transformed into gentamicin C2a, C2, and then CI. The biotransformation products were isolated using ion exchange and carbon column chromatographic procedures and identified through various analytical techniques. The study also compared the biotransformation capabilities of other Micromonospora species, such as M. zionensis and M. inyoensis, and found that they lacked the (4',5')-reduction activity present in M. sagamiensis. Instead, M. zionensis transformed sisomicin into antibiotic G-52 and verdamicin into a new antibiotic, VF3-1, which was suggested to be 6'-N-methylverdamicin based on chromatographic and mass spectrum data. The findings provide insights into the biosynthetic pathways of these antibiotics and their potential for further development.

13-(2-methylbenzyl) berberine is a more potent inhibitor of MexXY-dependent aminoglycoside resistance than berberine

10.3390/antibiotics8040212

The research focused on synthesizing berberine derivatives to inhibit MexXY-dependent aminoglycoside resistance in Pseudomonas aeruginosa. The study synthesized 11 berberine derivatives and tested their inhibitory activities against MexXY in both MexXY-positive and MexXY-negative P. aeruginosa strains. The most potent derivative, 13-(2-methylbenzyl) berberine (13-o-MBB), was found to reduce the minimum inhibitory concentrations (MICs) of various aminoglycosides significantly in a multidrug-resistant P. aeruginosa strain. Experiments involved assessing MICs, determining fractional inhibitory concentration (FIC) indices to evaluate synergistic effects, and conducting time-kill assays to measure bactericidal activity. The analyses included NMR and mass spectrometry for compound characterization and CLSI standards for categorizing antibiotic susceptibility. The study concluded that 13-o-MBB is a more potent inhibitor of MexXY-dependent aminoglycoside resistance than berberine, offering a promising approach to overcoming antibiotic resistance in P. aeruginosa.