Gentamicin

Base Information

• Chemical Name: Gentamicin
• CAS No.: 1403-66-3
• Molecular Formula: C21H43N5O7
• Molecular Weight: 477.60
• Hs Code.: 3004909090
• European Community (EC) Number: 215-765-8
• Nikkaji Number: J4.074F
• Wikipedia: Gentamicin
• Wikidata: Q422482
• NCI Thesaurus Code: C519
• RXCUI: 1596450
• Pharos Ligand ID: DR47YA5R4BCS
• Metabolomics Workbench ID: 131037
• ChEMBL ID: CHEMBL329592
• Mol file: 1403-66-3.mol

Synonyms:G Myticin;G-Myticin;Garamycin;Gentacycol;Gentamicin;Gentamicin Sulfate;Gentamicin Sulfate (USP);Gentamicins;Gentamycin;Gentamycins;Gentavet;Genticin;GMyticin;Sulfate, Gentamicin

Chemical Property of Gentamicin

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
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 477.31624873
• Heavy Atom Count: 33
• Complexity: 636

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:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Aminoglycosides
• Canonical SMILES: CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
• Recent ClinicalTrials: Use of Antibiotic Based Irrigation for Ureteroscopic Treatment of Urolithiasis
• Recent EU Clinical Trials: Short or Long Antibiotic Regimes in Orthopaedics (SOLARIO):
• Recent NIPH Clinical Trials: An open-label randomized controlled trial of ampicillin/cloxacillin and ceftriaxone for empirical treatment of infective endocarditis
• 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.