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.[H][C@]2(O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O)O[C@H](C)[C@H](C[C@@H]2N)NC(=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 | 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 |
| 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 |
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 |
|---|---|---|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
|
| Increased sensitivity to protein synthesis inhibitors in cells lacking tmRNA. | 2001 Dec |
|
| Establishment of a new cross of the rice blast fungus derived from Japanese differential strain Ina168 and hermaphroditic rice pathogen Guy11. | 2001 Jul |
|
| Coordination mode and reactivity of copper(II) complexes with kasugamycin. | 2001 Jun |
|
| Continuous culture of immobilized streptomyces cells for kasugamycin production. | 2001 May-Jun |
|
| 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 Dec |
|
| Instruction of translating ribosome by nascent peptide. | 2002 Sep 13 |
|
| Requirement for SAPK-JNK signaling in the induction of apoptosis by ribosomal stress in REH lymphoid leukemia cells. | 2003 Nov |
|
| [Techniques of diseases, insect pests and weeds control and their efficacy in bio-rational rice production]. | 2004 Jan |
|
| Drug resistance in Chromobacterium violaceum. | 2004 Mar 31 |
|
| Crystal structure of KsgA, a universally conserved rRNA adenine dimethyltransferase in Escherichia coli. | 2004 May 28 |
|
| New media for the semiselective isolation and enumeration of Xanthomonas campestris pv. mangiferaeindicae, the causal agent of mango bacterial black spot. | 2005 |
|
| A novel firmicute protein family related to the actinobacterial resuscitation-promoting factors by non-orthologous domain displacement. | 2005 Mar 17 |
|
| Role of mitochondrial ribosome-dependent translation in germline formation in Drosophila embryos. | 2005 Oct |
|
| DNA sequencing and transcriptional analysis of the kasugamycin biosynthetic gene cluster from Streptomyces kasugaensis M338-M1. | 2006 Jan |
|
| Antibiotic blocks mRNA path on the ribosome. | 2006 Oct |
|
| The antibiotic kasugamycin mimics mRNA nucleotides to destabilize tRNA binding and inhibit canonical translation initiation. | 2006 Oct |
|
| Structural analysis of kasugamycin inhibition of translation. | 2006 Oct |
|
| Structure of the chloroplast ribosome: novel domains for translation regulation. | 2007 Aug |
|
| Experimental characterization of Cis-acting elements important for translation and transcription in halophilic archaea. | 2007 Dec |
|
| Acidic pH shock induces the expressions of a wide range of stress-response genes. | 2008 Dec 16 |
|
| Sequence and structural evolution of the KsgA/Dim1 methyltransferase family. | 2008 Oct 29 |
|
| Global transcriptional response to mammalian temperature provides new insight into Francisella tularensis pathogenesis. | 2008 Oct 8 |
|
| ksgA mutations confer resistance to kasugamycin in Neisseria gonorrhoeae. | 2009 Apr |
|
| Control of glutamate receptor 2 (GluR2) translational initiation by its alternative 3' untranslated regions. | 2009 Dec |
|
| The chlamydial functional homolog of KsgA confers kasugamycin sensitivity to Chlamydia trachomatis and impacts bacterial fitness. | 2009 Dec 31 |
|
| An unexpected type of ribosomes induced by kasugamycin: a look into ancestral times of protein synthesis? | 2009 Jan 30 |
|
| Less is more for leaderless mRNA translation. | 2009 Jan 30 |
|
| Structural rearrangements in the active site of the Thermus thermophilus 16S rRNA methyltransferase KsgA in a binary complex with 5'-methylthioadenosine. | 2009 May 1 |
|
| CD8(+) T cells restrict Yersinia pseudotuberculosis infection: bypass of anti-phagocytosis by targeting antigen-presenting cells. | 2009 Sep |
|
| Isolation and activity of Xenorhabdus antimicrobial compounds against the plant pathogens Erwinia amylovora and Phytophthora nicotianae. | 2009 Sep |
|
| Natural toxins for use in pest management. | 2010 Aug |
|
| Modification of 16S ribosomal RNA by the KsgA methyltransferase restructures the 30S subunit to optimize ribosome function. | 2010 Dec |
|
| Exposure effect of fungicide kasugamycin on bacterial community in natural river sediment. | 2010 Jul |
|
| Analysis of antibiotic fungicide kasugamycin in irrigation water by high performance liquid chromatography. | 2010 Jul |
|
| Translation initiation region dependency of translation initiation in Escherichia coli by IF1 and kasugamycin. | 2010 Jun |
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
Sat Dec 16 02:14:44 GMT 2023
by
admin
on
Sat Dec 16 02:14:44 GMT 2023
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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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200132-83-8
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DTXSID20859996
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57369825
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |
