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Framycetin

Names

[ CAS No. ]:
119-04-0

[ Name ]:
Framycetin

[Synonym ]:
soframycine
framygen
enterfram
soframycin
NEOMYCIN B
actilin
antibiotique
actiline
EINECS 204-292-2
Neomycin solution

Biological Activity

[Description]:

Framycetin (Fradiomycin B; Neomycin B) is an aminoglycoside antibiotic. It inhibits hammerhead ribozyme with a Ki of 13.5 μM.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial
Research Areas >> Infection

[Target]

Ki: 13.5 μM (hammerhead ribozyme)[1]


[In Vitro]

Neomycin B is used clinically to treat hepatic encephalopathy (by reducing ammonium levels in the gut) and enteropathogenic Escherichia coli infections. Neomycin B targets the bacterial and human ribosome and affect translation. Addition of neomycin B, to an HCC cell line selectively inhibits production of the mature miRNA, boosts a downstream protein, and inhibits invasion[2]. Neomycin B interacts with various target RNAs that have no primary sequence homology. This means that the drug binds to a structural rather than a sequence motif of the RNA. Its primary cognate target is the decoding site of the 16S rRNA, but it also binds to the Rev-responsive element in HIV-1, group I introns, and the hammerhead ribozyme, and thus inhibits their biological function[3]. The aminoglycoside antibiotic neomycin B induces misreading of the genetic code during translation and inhibits several ribozymes. The ribosomal target site of neomycin B is the 16 S rRNA 1400 to 1500 region, which has been clearly demonstrated by dissecting this domain from a small RNA of 27 nucleotides. This small subdomain of the 16 S rRNA is protected from chemical modification by neomycin atthe same positions as in the context of the 30 S subunit[4].

[References]

[1]. Stage TK, et al. Inhibition of the hammerhead ribozyme by neomycin. RNA. 1995 Mar;1(1):95-101.

[2]. Childs-Disney JL, et al. Small Molecule Targeting of a MicroRNA Associated with Hepatocellular Carcinoma. ACS Chem Biol. 2016 Feb 19;11(2):375-80.

[3]. Stampfl S, et al. Monovalent ion dependence of neomycin B binding to an RNA aptamer characterized by spectroscopic methods. Chembiochem. 2007 Jul 9;8(10):1137-45.

[4]. Hoch I, et al. Antibiotic inhibition of RNA catalysis: neomycin B binds to the catalytic core of the td group I intron displacing essential metal ions. J Mol Biol. 1998 Sep 25;282(3):557-69.


[Related Small Molecules]

Puromycin 2HCl | Geneticin | Tunicamycin | Hygromycin B | Salinomycin | Avibactam sodium | Neomycin sulfate | Vaborbactam | Methicillin SodiuM | Rifampicin | Metronidazole | Carbenicillin disodium | Ceftazidime | Eravacycline dihydrochloride | cefotaxime sodium

Chemical & Physical Properties

[ Density]:
1.61 g/cm3

[ Boiling Point ]:
927.1ºC at 760 mmHg

[ Molecular Formula ]:
C23H46N6O13

[ Molecular Weight ]:
614.64400

[ Flash Point ]:
514.5ºC

[ Exact Mass ]:
614.31200

[ PSA ]:
353.11000

[ Index of Refraction ]:
1.6000 (estimate)

[ Storage condition ]:
2-8°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QP4025000
CHEMICAL NAME :
Neomycin B
CAS REGISTRY NUMBER :
119-04-0
BEILSTEIN REFERENCE NO. :
0101621
LAST UPDATED :
199612
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C23-H46-N6-O13
MOLECULAR WEIGHT :
614.75
WISWESSER LINE NOTATION :
T6OTJ B1Z CQ DQ EZ FO- AL6TJ BZ DZ EQ FO- BT5OTJ CQ E1Q DO- BT6OTJ CZ DQ EQ F1Z

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 1,127,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,741,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
220 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBTXAC "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59 Volume(issue)/page/year: 2,121,1957
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
24 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 27,677,1974

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R42/43

[ Safety Phrases ]:
S26;S45;S36/S37/S39

[ WGK Germany ]:
2

Precursor & DownStream


Related Compounds