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Substance Name: Kanamycin [INN:BAN]
RN: 59-01-8
UNII: EQK9Q303C5
InChIKey: SBUJHOSQTJFQJX-NOAMYHISSA-N

Note

  • Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.

Molecular Formula

  • C18-H36-N4-O11

Molecular Weight

  • 484.4994
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Kanamycin
  • Kanamycin A
  • Kanamycin [INN:BAN]

MeSH Heading

  • Kanamycin

Synonyms

  • 4,6-Diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-alpha-D-glucoside
  • 4-18-00-07631 (Beilstein Handbook Reference)
  • BRN 0061647
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1,4))-2-deoxy-
  • EINECS 200-411-7
  • Glucopyranoside, 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-, D-
  • HSDB 3107
  • Kanamicina
  • Kanamicina [Italian]
  • Kanamycin
  • Kanamycin A
  • Kanamycine
  • Kanamycine [INN-French]
  • Kanamycinum
  • Kanamycinum [INN-Latin]
  • Kantrex
  • KM (the Antibiotic)
  • UNII-EQK9Q303C5

Systematic Names

  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy-
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.4))-2-deoxy-
  • Kanamycin

Superlist Name

  • Kanamycin

Registry Numbers

CAS Registry Number

  • 59-01-8

FDA UNII

  • EQK9Q303C5

Other Registry Numbers

  • 11025-65-3
  • 19079-03-9
  • 64013-69-0
  • 717087-69-9
  • 936337-76-7

System Generated Number

  • 0000059018

Structure Descriptors

InChI

1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1

InChIKey

SBUJHOSQTJFQJX-NOAMYHISSA-N

Smiles

C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N

Toxicity

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) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR

SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR
American Review of Respiratory Disease. Vol. 82, Pg. 23, 1960.
mouse LD50 intracrebral 33750ug/kg (33.75mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: ATAXIA

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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -6.700 (none)   EST
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 3.29E-23 mm Hg 25 EST
Henry's Law Constant 2.91E-38 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.34E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.