Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H25N3O9.ClH.H2O |
| Molecular Weight | 433.839 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]2O)[C@@H](N)C[C@@H]1NC(=N)C(O)=O
InChI
InChIKey=URDOPMVCASNBEZ-IYWSOWMLSA-N
InChI=1S/C14H25N3O9.ClH.H2O/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22;;/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24);1H;1H2/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-;;/m1../s1
| Molecular Formula | C14H25N3O9 |
| Molecular Weight | 379.363 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Kasugamycin, an aminoglycoside antibiotic, potently inhibits both gram-positive and gram-negative bacteria, binds to the 30S subunit of the bacterial ribosome, and suppresses protein synthesis. Kasugamycin was studied in clinical use for urinary tract infections due to Pseudomonas aeruginosa and was investigated its therapeutic effect on respiratory infections due to Pseudomonas aeruginosa. Experiments in vitro showed that kasugamycin did not have any appreciable effect against a variety of bacteria tested. The only exceptions were several species of gram-negative bacteria, against which antibiotics that are more satisfactory already exist. That is why further evaluation of kasugamycin for potential human use as an antipseudomonal was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Modification of 16S ribosomal RNA by the KsgA methyltransferase restructures the 30S subunit to optimize ribosome function. | 2010-12 |
|
| Natural toxins for use in pest management. | 2010-08 |
|
| Exposure effect of fungicide kasugamycin on bacterial community in natural river sediment. | 2010-07 |
|
| Analysis of antibiotic fungicide kasugamycin in irrigation water by high performance liquid chromatography. | 2010-07 |
|
| Translation initiation region dependency of translation initiation in Escherichia coli by IF1 and kasugamycin. | 2010-06 |
|
| The chlamydial functional homolog of KsgA confers kasugamycin sensitivity to Chlamydia trachomatis and impacts bacterial fitness. | 2009-12-31 |
|
| Control of glutamate receptor 2 (GluR2) translational initiation by its alternative 3' untranslated regions. | 2009-12 |
|
| CD8(+) T cells restrict Yersinia pseudotuberculosis infection: bypass of anti-phagocytosis by targeting antigen-presenting cells. | 2009-09 |
|
| Isolation and activity of Xenorhabdus antimicrobial compounds against the plant pathogens Erwinia amylovora and Phytophthora nicotianae. | 2009-09 |
|
| Structural rearrangements in the active site of the Thermus thermophilus 16S rRNA methyltransferase KsgA in a binary complex with 5'-methylthioadenosine. | 2009-05-01 |
|
| ksgA mutations confer resistance to kasugamycin in Neisseria gonorrhoeae. | 2009-04 |
|
| An unexpected type of ribosomes induced by kasugamycin: a look into ancestral times of protein synthesis? | 2009-01-30 |
|
| Less is more for leaderless mRNA translation. | 2009-01-30 |
|
| Acidic pH shock induces the expressions of a wide range of stress-response genes. | 2008-12-16 |
|
| Sequence and structural evolution of the KsgA/Dim1 methyltransferase family. | 2008-10-29 |
|
| Global transcriptional response to mammalian temperature provides new insight into Francisella tularensis pathogenesis. | 2008-10-08 |
|
| Experimental characterization of Cis-acting elements important for translation and transcription in halophilic archaea. | 2007-12 |
|
| Structure of the chloroplast ribosome: novel domains for translation regulation. | 2007-08 |
|
| Antibiotic blocks mRNA path on the ribosome. | 2006-10 |
|
| The antibiotic kasugamycin mimics mRNA nucleotides to destabilize tRNA binding and inhibit canonical translation initiation. | 2006-10 |
|
| Structural analysis of kasugamycin inhibition of translation. | 2006-10 |
|
| DNA sequencing and transcriptional analysis of the kasugamycin biosynthetic gene cluster from Streptomyces kasugaensis M338-M1. | 2006-01 |
|
| Role of mitochondrial ribosome-dependent translation in germline formation in Drosophila embryos. | 2005-10 |
|
| A novel firmicute protein family related to the actinobacterial resuscitation-promoting factors by non-orthologous domain displacement. | 2005-03-17 |
|
| New media for the semiselective isolation and enumeration of Xanthomonas campestris pv. mangiferaeindicae, the causal agent of mango bacterial black spot. | 2005 |
|
| Crystal structure of KsgA, a universally conserved rRNA adenine dimethyltransferase in Escherichia coli. | 2004-05-28 |
|
| Drug resistance in Chromobacterium violaceum. | 2004-03-31 |
|
| [Techniques of diseases, insect pests and weeds control and their efficacy in bio-rational rice production]. | 2004-01 |
|
| Requirement for SAPK-JNK signaling in the induction of apoptosis by ribosomal stress in REH lymphoid leukemia cells. | 2003-11 |
|
| Human mitochondrial transcription factor B1 methylates ribosomal RNA at a conserved stem-loop. | 2003-01 |
|
| kasT gene of Streptomyces kasugaensis M338-M1 encodes a DNA-binding protein which binds to intergenic region of kasU-kasJ in the kasugamycin biosynthesis gene cluster. | 2002-12 |
|
| Differential inhibition of 30S and 70S translation initiation complexes on leaderless mRNA by kasugamycin. | 2002-10-04 |
|
| Instruction of translating ribosome by nascent peptide. | 2002-09-13 |
|
| Increased sensitivity to protein synthesis inhibitors in cells lacking tmRNA. | 2001-12 |
|
| Establishment of a new cross of the rice blast fungus derived from Japanese differential strain Ina168 and hermaphroditic rice pathogen Guy11. | 2001-07 |
|
| Continuous culture of immobilized streptomyces cells for kasugamycin production. | 2001-06-02 |
|
| Coordination mode and reactivity of copper(II) complexes with kasugamycin. | 2001-06 |
|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993-09-24 |
Sample Use Guides
The median minimal inhibitory concentration (MIC) of the Pseudomonas strains tested was 250 mug/ml and the bactericidal level was 500 mug/ml. Kasugamycin was found to be slightly more active in a more basic medium (Mycin Assay broth) in which the median MIC for 11 Pseudomonas strains was 125 mug/ml. Kasugamycin manifests a modest degree of serum binding. Kasugamycin did not have any appreciable effect against a variety of bacteria tested. The only exceptions were several species of gram-negative bacteria, against which more satisfactory antibiotics already exist.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:10:59 GMT 2025
by
admin
on
Mon Mar 31 21:10:59 GMT 2025
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| Record UNII |
5A9BN7V7QL
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| Record Status |
Validated (UNII)
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| Record Version |
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