Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H39N5O7 |
| Molecular Weight | 449.5423 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[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=VEGXETMJINRLTH-BOZYPMBZSA-N
InChI=1S/C19H39N5O7/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/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1
| Molecular Formula | C19H39N5O7 |
| Molecular Weight | 449.5423 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|||
| 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 |
|---|---|---|
| Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
|
| A comparison of anticryptosporidial activity of paromomycin with that of other aminoglycosides and azithromycin in immunosuppressed rats. | 1994 Oct |
|
| Discovery of selective, small-molecule inhibitors of RNA complexes--I. The Tat protein/TAR RNA complexes required for HIV-1 transcription. | 1997 Jun |
|
| Substituted xanthones as antimycobacterial agents, Part 2: Antimycobacterial activity. | 1998 May |
|
| 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 |
|
| 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 |
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.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:45:47 GMT 2023
by
admin
on
Fri Dec 15 15:45:47 GMT 2023
|
| Record UNII |
AV4A72IATD
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C2363
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
72396
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
AV4A72IATD
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
27784
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
26098-04-4
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
C76149
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
m5697
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID4023092
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
C100093
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
DB04729
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY | |||
|
58530
Created by
admin on Fri Dec 15 15:45:47 GMT 2023 , Edited by admin on Fri Dec 15 15:45:47 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
