kanamycin

Modify Date: 2024-01-03 16:25:00

kanamycin Structure
kanamycin structure
 Common Name kanamycin
CAS Number 59-01-8 Molecular Weight 484.499
Density 1.6±0.1 g/cm3 Boiling Point 809.5±65.0 °C at 760 mmHg
Molecular Formula C18H36N4O11 Melting Point N/A
MSDS N/A Flash Point 443.4±34.3 °C

 Use of kanamycin


Kanamycin (Kanamycin A) is an orally active antibacterial (gram-negative/positive bacteria) agent, inhibits translocation and causes misencoding by binding to the 70 S ribosomal subunit. Kanamycin shows good inhibitory activity to both M. tuberculosis (sensitive and drug-resistant ) and K. pneumonia, which can be used in studies of tuberculosis and pneumonia[1][2][3][4].

 Names

Name kanamycin A
Synonym More Synonyms

 kanamycin Biological Activity

Description Kanamycin (Kanamycin A) is an orally active antibacterial (gram-negative/positive bacteria) agent, inhibits translocation and causes misencoding by binding to the 70 S ribosomal subunit. Kanamycin shows good inhibitory activity to both M. tuberculosis (sensitive and drug-resistant ) and K. pneumonia, which can be used in studies of tuberculosis and pneumonia[1][2][3][4].
Related Catalog
In Vitro Kanamycin (0.1-100 μg/mL; 2 weeks) exhibits good antibacterial activity (MIC=1-5 μg/mL) to various strains of mycobacteria in vitro[1]. Cell Viability Assay[1] Cell Line: mycobacteria H37Rv, H2, H37RvR-PAS, Ravenel, Kirchbergand and BCG. Concentration: 0.1-100 μg/mL Incubation Time: 2 weeks Result: Showed good antibacterial activity to various strains of mycobacteria (H37Rv, H2, H37RvR-PAS, Ravenel, and BCG) with MICs were 1 μg/mL and 5 μg/mL for strain of Kirchbergand.
In Vivo Kanamycin (2, 4 mg/kg; s.c.; once daily, 6 times a week for 3 weeks) inhibits growth of bovine tubercle bacilli in lung and spleen of mice[1]. Kanamycin (1.25, 5 mg/kg; s.c.; single (at 3 h after infection)) inhibits the multiplication of K. pneumonia DT-S in lung, trachea, and blood of mice and in proportion to the dose administration, and also increases the survival rate of mice[2]. Animal Model: Inbred strain normal mice (14-16 g; bovine tubercle bacilli (Ravenel strain) infected model)[1]. Dosage: 2, 4 mg/kg Administration: Subcutaneous injection; once daily, 6 times a week for 3 weeks. Result: Exerted a marked effect to inhibit the multiplication of the tuberculosis in vivo, especially in the lung of mice. Animal Model: Slc:ICR male mice (4-week-old; 18-24 g; K. pneumonia DT-S infection model (by the aerosol method))[2]. Dosage: 1.25, 5 mg/kg Administration: Subcutaneous administration; single (at 3 h after infection). Result: Suppressed the growth of K. pneumonia DT-S in lung, trachea, and blood in proportion to the dose administration. Resulted in 90% survival at 6 days after infection (negative control group: all died within 4 days), and cleared the K. pneumonia DT-S from lung, trachea, and blood of mice within 48 h (when dosage at 5 mg/kg).
References

[1]. YANAGISAWA K, et al. Studies on kanamycin, a new antibiotic against tubercle bacilli. I. Effect on virulent tubercle bacilli in vitro and in mice. J Antibiot (Tokyo). 1957 Nov;10(6):233-5.

[2]. Nishi T, et al. Experimental respiratory tract infection with Klebsiella pneumoniae DT-S in mice: chemotherapy with kanamycin. Antimicrob Agents Chemother. 1980 Mar;17(3):494-505.

[3]. Misumi M, et al. Interaction of kanamycin and related antibiotics with the large subunit of ribosomes and the inhibition of translocation. Biochem Biophys Res Commun. 1978 Sep 29;84(2):358-65.

[4]. Misumi M, et al. Mechanism of inhibition of translocation by kanamycin and viomycin: a comparative study with fusidic acid. Biochem Biophys Res Commun. 1980 Jan 29;92(2):647-54.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 809.5±65.0 °C at 760 mmHg
Molecular Formula C18H36N4O11
Molecular Weight 484.499
Flash Point 443.4±34.3 °C
Exact Mass 484.238068
PSA 282.61000
LogP -2.58
Vapour Pressure 0.0±6.5 mmHg at 25°C
Index of Refraction 1.670

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WK1962000
CHEMICAL NAME :
D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-a mino-6-deoxy-alpha- D-glucopyranosyl-(1-4))-2-deoxy-
CAS REGISTRY NUMBER :
59-01-8
BEILSTEIN REFERENCE NO. :
0061647
LAST UPDATED :
199706
DATA ITEMS CITED :
27
MOLECULAR FORMULA :
C18-H36-N4-O11
MOLECULAR WEIGHT :
484.58
WISWESSER LINE NOTATION :
T6OTJ CQ DZ EQ F1Q BO- BL6TJ AZ CQ EZ DO- BT6OTJ CQ 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 - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1515 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4070 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
437 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1014 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20700 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
794 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
115 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
54 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
33750 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Cardiac - other changes Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1385 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
960 mg/kg/4D-I
TOXIC EFFECTS :
Blood - changes in other cell count (unspecified) Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
12 gm/kg/30D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
3600 mg/kg
SEX/DURATION :
female 1-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
3600 mg/kg
SEX/DURATION :
female 12-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
3500 mg/kg
SEX/DURATION :
female 12-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear

MUTATION DATA

TYPE OF TEST :
DNA repair
TEST SYSTEM :
Bacteria - Bacillus subtilis
DOSE/DURATION :
27 ug/L
REFERENCE :
WATRAG Water Research. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 0BW, UK) V.1- 1967- Volume(issue)/page/year: 14,1613,1980 *** REVIEWS *** TOXICOLOGY REVIEW CLANA4 Clinical Anesthesia. (Philadelphia, PA 19103) V.1-11, 1963-76. Volume(issue)/page/year: 10(Pt 1),283,1973 TOXICOLOGY REVIEW MMWOAU Muenchener Medicinische Wochenschrift. (Munich, Fed. Rep. Ger.) V.33-115, 1886-1973. Volume(issue)/page/year: 115,1661,1973 TOXICOLOGY REVIEW INTEAG Internist. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1960- Volume(issue)/page/year: 15,7,1974 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 38,409,1965

 Safety Information

WGK Germany 2

 Synonyms

KANAMYCIN
4,6-Diamino-3-[(6-amino-6-deoxyhexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxyhexopyranoside
kanamycin from Streptomyces kanamyceticus
d-deoxydi
Kannamycin Monosulfate
d-xydi
kanamicina
KanamycinMonosulfateA
Hexopyranoside, 4,6-diamino-3-[(6-amino-6-deoxyhexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-
gentamicin A
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Related Compounds: More...
Kanamycin
8063-07-8
kanamycin C
2280-32-2
kanamycin a
70560-51-9
Bekanamycin
4696-76-8
Deoxykanamycin
5487-00-3
Ahb-kanamycin A
117325-82-3
Ahbd-kanamycin B
83071-96-9
Kanamycin sulfate
25389-94-0
kanamycin sulfate
133-92-6
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