Kasugamycin Hydrochloride

Names

[ CAS No. ]:
19408-46-9

[ Name ]:
Kasugamycin Hydrochloride

[Synonym ]:
KASUGAMYCIN HYDROCHLORIDE HYDRATE
3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl]-D-chiro-inositol monohydrochloride
MFCD00149375
1L-1,3,4/2,5,6-1-deoxy-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-4-(α-iminoglycino)-α-D-arabino-hexopyranoside hydrochloride
(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-Pentahydroxycyclohexyl 2-amino-4-{[carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside hydrochloride (1:1)
(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-{[carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-a-D-arabino-hexopyranoside hydrochloride (1:1)
KASUGAMYCIN HYDROCHL
kasugamycin,monohydrochloride
a-D-arabino-hexopyranoside, (1a,2b,3a,4a,5b,6b)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-, hydrochloride (1:1)
kasugamycin (jmaff)
KASUGAMYCIN HCL HYDRATE
kasumin
KasugaMycin HCl
3-o-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-d-arabino-hexopyranosyl]-d-chiro-inositol
Kasugamycin Hydrochloride
[5-amino-2-methyl-6-(2,3,4,5,6-pentahydroxycyclohexyloxy)tetrahydropyran-3-yl]amino-α-iminoacetic acid hydrochloride
α-D-arabino-Hexopyranoside, (1α,2β,3α,4α,5β,6β)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-, hydrochloride (1:1)
Kasugamycin hydrochloride from Streptomyces kasugaensis

Biological Activity

[Description]:

Kasugamycin hydrochloride (Ksg hydrochloride) is an antibiotic which binds both the 30S and 70S ribosome but not isolated 50S subunits. Kasugamycin hydrochloride (Ksg hydrochloride) mimics mRNA nucleotides to destabilize tRNA binding and inhibit canonical translation initiation[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Schluenzen F, et al. The antibiotic kasugamycin mimics mRNA nucleotides to destabilize tRNA binding and inhibit canonical translation initiation. Nat Struct Mol Biol. 2006 Oct;13(10):871-8.

[2]. Schuwirth BS, et al. Structural analysis of kasugamycin inhibition of translation. Nat Struct Mol Biol. 2006 Oct;13(10):879-86.

Chemical & Physical Properties

[ Density]:
1.97g/cm3

[ Boiling Point ]:
628.2ºC at 760mmHg

[ Melting Point ]:
203ºC (dec)

[ Molecular Formula ]:
C₁₄H₂₆ClN₃O₉

[ Molecular Weight ]:
415.824

[ Flash Point ]:
333.7ºC

[ Exact Mass ]:
415.135742

[ PSA ]:
218.81000

[ Vapour Pressure ]:
2.04E-18mmHg at 25°C

[ Index of Refraction ]:
1.738

[ Water Solubility ]:
H2O: soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM7521800

CHEMICAL NAME :: D-chiro-Inositol, 3-O-(2-amino-4-((carboxyiminomethyl)amino)-2,3,4,6-te tradeoxy-alpha-D- arabino-hexopyranosyl)-, monohydrochloride

CAS REGISTRY NUMBER :: 19408-46-9

LAST UPDATED :: 199410

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C14-H25-N3-O9.Cl-H

MOLECULAR WEIGHT :: 415.88

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 22 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (10),66,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (10),66,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (10),66,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (10),66,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20500 mg/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 21,206,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AACHAX Antimicrobial Agents and Chemotherapy (1961-70). (Ann Arbor, MI) 1961-70. For publisher information, see AMACCQ. Volume(issue)/page/year: -,225,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12 gm/kg

TOXIC EFFECTS :: Vascular - shock Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - other changes

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 21,206,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3850 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AACHAX Antimicrobial Agents and Chemotherapy (1961-70). (Ann Arbor, MI) 1961-70. For publisher information, see AMACCQ. Volume(issue)/page/year: -,225,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (2),18,1970

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (10),66,1972

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
22-24/25-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
NM7521800

Articles

Inactivation of KsgA, a 16S rRNA methyltransferase, causes vigorous emergence of mutants with high-level kasugamycin resistance.

Antimicrob. Agents Chemother. 53 , 193-201, (2009)

The methyltransferases RsmG and KsgA methylate the nucleotides G535 (RsmG) and A1518 and A1519 (KsgA) in 16S rRNA, and inactivation of the proteins by introducing mutations results in acquisition of l...

Translation-independent localization of mRNA in E. coli.

Science 331(6020) , 1081-4, (2011)

Understanding the organization of a bacterial cell requires the elucidation of the mechanisms by which proteins localize to particular subcellular sites. Thus far, such mechanisms have been suggested ...

Control of glutamate receptor 2 (GluR2) translational initiation by its alternative 3' untranslated regions.

Mol. Pharmacol. 76(6) , 1145-9, (2009)

Four major glutamate receptor 2 (GluR2) transcripts differing in size (approximately 4 and approximately 6 kilobases) due to alternative 3' untranslated regions (UTRs), and also containing alternative...