Name: KANAMYCIN
SKU: 59-01-8

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Basic Information

Molecular Structure:
CAS No.:	59-01-8
Name:	KANAMYCIN
Article Data:	14

Formula:	C18H36 N4 O11
Molecular Weight:	484.504
Synonyms:	KanamycinA (7CI);4,6-Diamino-2-hydroxy-1,3-cyclohexane 3,6'-diamino-3,6'-dideoxydi-a-D-glucoside;KM;Kanacin;Kanamycin;
EINECS:	200-411-7
Density:	1.62g/cm³
Boiling Point:	809.5°Cat760mmHg
Flash Point:	443.4°C
Safety:	Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
PSA:	282.61000
LogP:	-4.49020

Synthetic route

: 3847-27-6, 25389-94-0, 64013-70-3, 81129-79-5, 84278-20-6, 94108-19-7, 94237-36-2
Kanamycin A sulfate

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
With Amberlite IRA-400-OH In water	91%
With Amberlite IRA-400 -OH In water
With Amberlite-IRA 400 (OH-)

: C34H46N4O16

A: 59-01-8
kanamycin A

B: 1-deamino-1-dehydro-1-hydroxyiminokanamycin A

Conditions

Conditions	Yield
With hydrogen; acetic acid; palladium In water under 760 Torr; for 2h; Ambient temperature;	A 4.7% B 83%

: 98084-09-4
6'-N-hydroxykanamicyn A (sulfate)

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide In water under 2660 Torr; for 2h; Ambient temperature; Yield given;

: 80860-34-0
di-tert-butyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,4S,5S,6R)-6-(((tert-butoxycarbonyl)amino)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
tetrafluoroboric acid at 20℃; for 0.1h;

: 1-deamino-1-dehydro-1-hydroxyiminokanamycin A

A: 81076-65-5
1-epi-kanamycin A

B: 59-01-8
kanamycin A

Conditions

Conditions	Yield
With ammonium hydroxide; hydrogen; nickel under 2280 Torr; for 5h; Ambient temperature;

: 74256-73-8
3,6'-bis(N-benzyloxycarbonyl)-3"-N-(trifluoroacetyl)kanamycin A

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / sodium tungstate dihydrate, aq. H2O2 / various solvent(s) / Ambient temperature 2: aq. NH4OH / various solvent(s) / Ambient temperature 3: 4.7 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 86 percent / sodium tungstate dihydrate, aq. H2O2 / various solvent(s) / Ambient temperature 2: aq. NH4OH / various solvent(s) / Ambient temperature 3: 83 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature 4: H2, aq. NH4OH / Raney Ni / 5 h / 2280 Torr / Ambient temperature View Scheme

: C34H46N4O16

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature 2: H2, aq. NH4OH / Raney Ni / 5 h / 2280 Torr / Ambient temperature View Scheme

: 3,6'-bis(N-benzyloxycarbonyl)-1-deamino-1-dehydro-1-hydroxyimino-3"-N-(trifluoroacetyl)kanamycin A

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NH4OH / various solvent(s) / Ambient temperature 2: 4.7 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: aq. NH4OH / various solvent(s) / Ambient temperature 2: 83 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature 3: H2, aq. NH4OH / Raney Ni / 5 h / 2280 Torr / Ambient temperature View Scheme

: 2'-oxokanamycin

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
With His-tagged NADPH-dependent reductase; potassium chloride; glycerol; NADPH at 28℃; pH=7.5; Tris-HCl buffer; Enzymatic reaction; stereoselective reaction;

: C22H43N5O13*2H2O4S

: 59-01-8
kanamycin A

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 20h; Reagent/catalyst; Solvent; Temperature;

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Chemistry

Product Name: Kanamycin (CAS NO.59-01-8)

Molecular Formula: C₁₈H₃₆N₄O₁₁
Molecular Weight: 484.5g/mol
Mol File: 59-01-8.mol
Einecs: 200-411-7
Boiling point: 809.5 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 443.4 °C
Density: 1.62 g/cm³
Surface Tension: 104.4 dyne/cm
Enthalpy of Vaporization: 134 kJ/mol
Vapour Pressure: 2.47E-30 mmHg at 25°C
XLogP3-AA: -6.9
H-Bond Donor: 11
H-Bond Acceptor: 15

Uses

Kanamycin (CAS NO.59-01-8) is for the production of sulfuric acid amikacin, kanamycin monosulfate, and pairs of kanamycin sulfate intermediates.
It is used in molecular biology as a selective agent most commonly to isolate bacteria (e.g., E. coli) which have taken up genes (e.g., of plasmids) coupled to a gene coding for kanamycin resistance (primarily Neomycin phosphotransferase II [NPT II/Neo]). Bacteria that have been transformed with a plasmid containing the kanamycin resistance gene are plated on kanamycin (50-100mg/L) containing agar plates or are grown in media containing kanamycin (50-100mg/L). Only the bacteria that have successfully taken up the kanamycin resistance gene become resistant and will grow under these conditions. As a powder kanamycin is white to off-white and is soluble in water (50mg/ml).
At least one such gene, Atwbc19 is native to a plant species, of comparatively large size and its coded protein acts in a manner which decreases the possibility of Horizontal Gene Transfer from the plant to bacteria; it may be incapable of giving resistance to kanamycin to bacteria even if gene transfer occurs.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	intraperitoneal	1385mg/kg (1385mg/kg)		Antibiotiki. Vol. 19, Pg. 552, 1974.
human	TDLo	unreported	843mg/kg/17W- (843mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION	American Review of Respiratory Disease. Vol. 82, Pg. 23, 1960.
mouse	LD50	intracrebral	33750ug/kg (33.75mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Chemotherapy Vol. 17, Pg. 1664, 1969.
mouse	LD50	intramuscular	54mg/kg (54mg/kg)		Bollettino Chimico Farmaceutico. Vol. 98, Pg. 224, 1959.
mouse	LD50	intraperitoneal	794mg/kg (794mg/kg)		Chemotherapy Vol. 16, Pg. 371, 1971.
mouse	LD50	intravenous	115mg/kg (115mg/kg)		Minerva Farmaceutica. Vol. 11, Pg. 108, 1962.
mouse	LD50	oral	20700ug/kg (20.7mg/kg)		Antibiotiki. Vol. 19, Pg. 552, 1974.
mouse	LD50	subcutaneous	1350mg/kg (1350mg/kg)		Antimicrobial Agents and Chemotherapy Vol. -, Pg. 341, 1967.
rabbit	LD50	intravenous	150mg/kg (150mg/kg)		"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 690, 1978.
rat	LD50	intramuscular	> 1014mg/kg (1014mg/kg)	BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: CYANOSIS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Chemotherapy Vol. 29(Suppl,
rat	LD50	intraperitoneal	1515mg/kg (1515mg/kg)		Antibiotiki. Vol. 19, Pg. 552, 1974.
rat	LD50	intravenous	437mg/kg (437mg/kg)		Chemotherapy Vol. 29(Suppl,
rat	LD50	oral	> 10gm/kg (10000mg/kg)		Chemotherapy Vol. 29(Suppl,
rat	LD50	subcutaneous	4070mg/kg (4070mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 176, Pg. 59, 1968.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.

Specification

Kanamycin ,its CAS NO. is 59-01-8,the synonyms is Kanamycin a ; Kanamycin base ; 2-Deoxy-y-alpha-d-glucopyranosyl- ; 4,6-Diamino-2-hydroxy-1,3-cyclohexane3,6'diamino-3,6'-dideoxydi-alpha-d-gluc ; 4,6-Diamino-2-hydroxy-1,3-cyclohexane3,6'diamino-3,6'-dideoxydi-alpha-d-glucos ; D-deoxydi ; D-streptamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1.fwdarw.6)-o-6-amin .

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Chemistry

Uses

Toxicity Data With Reference

Consensus Reports

Safety Profile

Specification