Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H39N5O7.H2O4S |
| Molecular Weight | 547.621 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.[H][C@]3(O[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O[C@@]2([H])OC[C@](C)(O)[C@H](NC)[C@H]2O)[C@H]1O)O[C@H](CN)CC[C@H]3N
InChI
InChIKey=HNCAOLPMSASREN-UCMBPTNBSA-N
InChI=1S/C19H39N5O7.H2O4S/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m0./s1
Gentamicin is an antibiotic of the aminoglycoside group, is derived from the growth of Micromonospora purpurea, an actinomycete. Gentamicin is a complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1a that have different patterns of methylation at the 69 position of the ring. Gentamicin C1a is a broad-spectrum antibiotic against Gram-positive and Gram-negative bacteria but may cause ear and kidney damage. Gentamicin C1a binds to the A-site RNA of the 30S bacterial ribosomal subunit. Adverse reactions include adverse renal effects, neurotoxicity (dizziness, vertigo, tinnitus, roaring in the ears, hearing loss, peripheral neuropathy or encephalopathy), respiratory depression, lethargy, confusion, depression, visual disturbances, etc.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL614640 |
0.01 µM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | GENTAMICIN SULFATE Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1982 |
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| Curative | GENTAMICIN SULFATE Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1982 |
|||
| Curative | GENTAMICIN SULFATE Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1982 |
|||
| Curative | GENTAMICIN SULFATE Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1982 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro and in vivo susceptibility of atypical mycobacteria to various drugs. | 1981 Sep-Oct |
|
| In vitro susceptibility of Mycobacterium avium complex to antibacterial agents. | 1987 Nov |
|
| Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome. | 1987 Oct |
|
| Liposome-encapsulated-gentamicin therapy of Mycobacterium avium complex infection in beige mice. | 1990 Jun |
|
| Bacteriostatic and bactericidal activities of gentamicin alone and in combination with clarithromycin against Mycobacterium avium. | 1992 Aug |
|
| TLC G-65 in combination with other agents in the therapy of Mycobacterium avium infection in beige mice. | 1992 Jun |
|
| Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
|
| A comparison of anticryptosporidial activity of paromomycin with that of other aminoglycosides and azithromycin in immunosuppressed rats. | 1994 Oct |
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| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
|
| In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria. | 1997 Jul |
|
| Discovery of selective, small-molecule inhibitors of RNA complexes--I. The Tat protein/TAR RNA complexes required for HIV-1 transcription. | 1997 Jun |
|
| Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. | 1997 May |
|
| Substituted xanthones as antimycobacterial agents, Part 2: Antimycobacterial activity. | 1998 May |
|
| Substituted xanthones as antimycobacterial agents. Part 3: QSAR investigations. | 1999 Mar |
|
| Antimycobacterial agents differ with respect to their bacteriostatic versus bactericidal activities in relation to time of exposure, mycobacterial growth phase, and their use in combination. | 2005 Jun |
|
| N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles. First synthesis and biological evaluation. | 2007 Sep |
|
| In vivo efficacy and pharmacokinetics of tomopenem (CS-023), a novel carbapenem, against Pseudomonas aeruginosa in a murine chronic respiratory tract infection model. | 2008 Dec |
|
| Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents. | 2009 Aug |
|
| Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents. | 2010 Mar 1 |
|
| Effect of ribosome-targeting antibiotics on streptomycin-resistant Mycobacterium mutants in the rpsL gene. | 2013 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Gentamicin injection may be given IM or IV. Gentamicin is recommended to be administered in three equal doses every eight hours. For adult patients with life-threatening infections, dosages up to 5 mg/kg/day may be administered in three or four equal doses.
Adults: 3 mg/kg/day
Adult patients with life-threatening infections: 5 mg/kg/day
Children: 6 to 7.5 mg/kg/day
Infants and Neonates: 7.5 mg/kg/day
Premature or Full-Term Neonates One Week of Age or Less: 5 mg/kg/day
Route of Administration:
Other
In Vitro Use Guide
Curator's Comment: Binding of each gentamicin component to the ribosome and to a model RNA oligonucleotide was studied biochemically and the structure of the RNA complexed to gentamicin C1a was solved using magnetic resonance nuclear spectroscopy. Gentamicin C1a binds in the major groove of the RNA. Rings I and II of gentamicin direct specific RNA-drug interactions. Ring III of gentamicin, which distinguishes this subclass of aminoglycosides, also directs specific RNA interactions with conserved base pairs.
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DBSALT002339
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DTXSID40191148
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21115148
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37713-04-5
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
