Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H43N5O7 |
| Molecular Weight | 477.5954 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1
InChI
InChIKey=CEAZRRDELHUEMR-CAMVTXANSA-N
InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
| Molecular Formula | C21H43N5O7 |
| Molecular Weight | 477.5954 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugbank.ca/drugs/DB00798http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdfCurator's Comment: Description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00798
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ca625340-377b-4256-92e2-d62471a8d852
Sources: https://www.drugbank.ca/drugs/DB00798http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdf
Curator's Comment: Description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00798
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ca625340-377b-4256-92e2-d62471a8d852
Gentamicin is an antibiotic of the aminoglycoside group, is derived by the growth of Micromonospora purpurea, an actinomycete. Gentamicin is a complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1a. Gentamicin is a broad-spectrum antibiotic, but may cause ear and kidney damage. Gentamicin binds to the prokaryotic ribosome, inhibiting protein synthesis in susceptible bacteria. It is bactericidal in vitro against Gram-positive and Gram-negative bacteria. 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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6431059https://books.google.ru/books?id=tMfQvYKNVz4C&pg=PA5&lpg=PA5&dq=gentamicin+not+readily+crosses+the+blood-brain+barrier&source=bl&ots=1t9bQV5WFT&sig=4pWiwGUCNf8NuKWscVRE6Ag9aHI&hl=ru&sa=X&ved=0ahUKEwivs63J9u_LAhWrCpoKHUZgA90Q6AEIQzAE#v=onepage&q=gentamicin%20not%20readily%20crosses%20the%20blood-brain%20barrier&f=false
Curator's Comment: Gentamicin does not readily cross the blood–brain barrier.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL354 |
|||
Target ID: CHEMBL352 |
|||
Target ID: 30S subunit of the bacterial ribosome |
|||
Target ID: CHEMBL614640 |
2.0 µM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
|||
| Curative | GARAMYCIN 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 Date1970 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Aminoglycoside suppression of nonsense mutations in severe hemophilia. | 2005-11-01 |
|
| Gentamicin induces Jun-AP1 expression and JNK activation in renal glomeruli and cultured mesangial cells. | 2005-09-16 |
|
| [Expression of heat shock protein 70 mRNA in guinea pig cochlea with ototoxicity of gentamicin]. | 2005-06-25 |
|
| Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor. | 2005-05 |
|
| Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. | 2005-04-20 |
|
| Pyomyositis caused by methicillin-resistant Staphylococcus aureus. | 2005-04-07 |
|
| Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol. | 2005-04 |
|
| Role of the renin-angiotensin system on the parathyroid hormone-related protein overexpression induced by nephrotoxic acute renal failure in the rat. | 2005-04 |
|
| Protective effect of L-arginine intake on the impaired renal vascular responses in the gentamicin-treated rats. | 2005 |
|
| Correction of ATM gene function by aminoglycoside-induced read-through of premature termination codons. | 2004-11-02 |
|
| Delayed diagnosis of penicillin-resistant Streptococcus mitis endocarditis following single-dose amoxicillin prophylaxis in a child. | 2004-10 |
|
| Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center. | 2004-10 |
|
| In vivo efficacy of linezolid in combination with gentamicin for the treatment of experimental endocarditis due to methicillin-resistant Staphylococcus aureus. | 2004-10 |
|
| Early gene expression in the organ of Corti exposed to gentamicin. | 2004-09 |
|
| Effects of some antibiotics on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro and in vivo study. | 2004-08 |
|
| Efficacy of the combination ampicillin plus ceftriaxone in the treatment of a case of enterococcal endocarditis due to Enterococcus faecalis highly resistant to gentamicin: efficacy of the "ex vivo" synergism method. | 2004-08 |
|
| Influence of spironolactone treatment on gentamicin-induced nephrotoxicity in rats. | 2004-07 |
|
| Altered NMDA receptor expression in renal toxicity: Protection with a receptor antagonist. | 2004-07 |
|
| Gentamicin treatment induces simultaneous mesangial proliferation and apoptosis in rats. | 2004-06 |
|
| Hematopoietic and nonhematopoietic potentials of Hoechst(low)/side population cells isolated from adult rat kidney. | 2004-05 |
|
| Deficiency of polycystin-2 reduces Ca2+ channel activity and cell proliferation in ADPKD lymphoblastoid cells. | 2004-05 |
|
| alpha-L-iduronidase premature stop codons and potential read-through in mucopolysaccharidosis type I patients. | 2004-04-30 |
|
| Plasma protein extravasation and vascular endothelial growth factor expression with endothelial nitric oxide synthase induction in gentamicin-induced acute renal failure in rats. | 2004-04 |
|
| Absence of dystrophin in mice reduces NO-dependent vascular function and vascular density: total recovery after a treatment with the aminoglycoside gentamicin. | 2004-04 |
|
| Identification of putative gene based markers of renal toxicity. | 2004-03 |
|
| Evaluation of factors to decrease bioavailability of cyclosporin A in rats with gentamicin-induced acute renal failure. | 2004-03 |
|
| Effect of tempol (4-hydroxy tempo) on gentamicin-induced nephrotoxicity in rats. | 2004-02 |
|
| Inhibition of nuclear factor-kappaB activation attenuates tubulointerstitial nephritis induced by gentamicin. | 2004 |
|
| Gentamicin-induced correction of CFTR function in patients with cystic fibrosis and CFTR stop mutations. | 2003-10-09 |
|
| Intratympanic gentamicin for intractable Meniere's disease: 5-year follow-up. | 2003-10 |
|
| Hearing loss after intratympanic gentamicin therapy for unilateral Ménière's Disease. | 2003-09 |
|
| Protective effects of glycyrrhizin on gentamicin-induced acute renal failure in rats. | 2003-09 |
|
| Classification and rescue of ROMK mutations underlying hyperprostaglandin E syndrome/antenatal Bartter syndrome. | 2003-09 |
|
| Diallyl disulfide ameliorates gentamicin-induced oxidative stress and nephropathy in rats. | 2003-07-18 |
|
| Acute renal failure and cystic fibrosis. | 2003-07 |
|
| Gentamicin administration in Duchenne patients with premature stop codon. Preliminary results. | 2003-05 |
|
| Protective effect of Pongamia pinnata flowers against cisplatin and gentamicin induced nephrotoxicity in rats. | 2003-01 |
|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993-09-24 |
|
| Detection of uremic peaks in dogs by anion exchange high performance liquid chromatography. | 1992-10 |
|
| Gentamicin-induced hypercalciuria in the rat: assessment of nephron site involved. | 1992-10 |
|
| Changes in concentration of essential metals in kidneys and urine as indices of gentamicin nephrotoxicity in female Wistar rats. | 1992-09 |
|
| Chrononephrotoxicity in rat of a vancomycin and gentamicin combination. | 1992-07 |
|
| Calcium supplementation and thyroid hormone protect against gentamicin-induced inhibition of proximal tubular Na+,K(+)-ATPase activity and other renal functional changes. | 1992-06 |
|
| Effects of aminoglycoside antibiotics on the auditory brainstem response and post rotatory nystagmus in rats. | 1992-05 |
|
| An investigation of the acute effect of gentamicin on the renal handling of electrolytes in the rat. | 1992-04 |
|
| Sense of smell after gentamicin nose-drops. | 1992-02-01 |
|
| Effects of desoxycorticosterone acetate (DOCA) plus saline drinking on gentamicin-mediated nephropathy in rats. | 1992 |
|
| Comparison of methods for prediction of nephrotoxicity during development. | 1992 |
|
| Reactive oxygen metabolites in toxic acute renal failure. | 1992 |
|
| [The intratympanic treatment of Menière's disease with ototoxic antibiotics. A follow-up study of 55 cases (author's transl)]. | 1977-05 |
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
For patients with life-threatening infections, dosages up to 5 mg/kg/day may be administered in three or four equal doses. The dosage should be reduced to 3 mg/kg/day as soon as clinically indicated
Route of Administration:
Other
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
I904Y9FPPV
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| Record Status |
Validated (UNII)
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C2363
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72395
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C76148
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m5697
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ACTIVE MOIETY |
