KASUGAMYCIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H25N3O9.ClH
Molecular Weight	415.824
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=ZDRBJJNXJOSCLR-NZXABURVSA-N

InChI=1S/C14H25N3O9.ClH/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/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-;/m1./s1

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6049299 | https://www.ncbi.nlm.nih.gov/pubmed/5299330 | https://www.ncbi.nlm.nih.gov/pubmed/4961002

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

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial 30S ribosome 3 Target ID: bacterial 30S ribosome Sources: https://www.ncbi.nlm.nih.gov/pubmed/4931565	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5299159	Curative		Not Provided 504	Unknown Approved Use Unknown
Respiratory infections 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5299330	Curative		Not Provided 504	Unknown Approved Use Unknown

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	8402886
Increased sensitivity to protein synthesis inhibitors in cells lacking tmRNA.	2001 Dec	11780628
Continuous culture of immobilized streptomyces cells for kasugamycin production.	2001 May-Jun	11386865
Instruction of translating ribosome by nascent peptide.	2002 Sep 13	12228716
Requirement for SAPK-JNK signaling in the induction of apoptosis by ribosomal stress in REH lymphoid leukemia cells.	2003 Nov	12970763
[Techniques of diseases, insect pests and weeds control and their efficacy in bio-rational rice production].	2004 Jan	15139200
Natural toxins for use in pest management.	2010 Aug	22069667

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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 `Sat Dec 16 02:13:53 GMT 2023` Edited by `admin` on `Sat Dec 16 02:13:53 GMT 2023`
Record UNII	SXA18D440T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KASUGAMYCIN HYDROCHLORIDE

Common Name

English

D-CHIRO-INOSITOL, 3-O-(2-AMINO-4-((CARBOXYIMINOMETHYL)AMINO)-2,3,4,6-TETRADEOXY-.ALPHA.-D-ARABINO-HEXOPYRANOSYL)-, HYDROCHLORIDE (1:1)

Common Name

English

KASUMIN

Common Name

English

Code System Code Type Description

CAS

19408-46-9