Identification
- Summary
Kanamycin is an aminoglycoside antibiotic agent used in the treatment of various infections caused by susceptible bacteria.
- Generic Name
- Kanamycin
- DrugBank Accession Number
- DB01172
- Background
Kanamycin (also known as kanamycin A) is an aminoglycoside bacteriocidal antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Kanamycin (DB01172)
- Weight
- Average: 484.4986
Monoisotopic: 484.238058014 - Chemical Formula
- C18H36N4O11
- Synonyms
- 4,6-diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-α-D-glucoside
- 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-D-glucopyranoside
- Kanamycin A
- External IDs
- 8063-07-8
Pharmacology
- Indication
For treatment of infections where one or more of the following are the known or suspected pathogens: E. coli, Proteus species (both indole-positive and indole-negative), E. aerogenes, K. pneumoniae, S. marcescens, and Acinetobacter species.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Kanamycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
- Mechanism of action
Aminoglycosides like kanamycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Kanamycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
Target Actions Organism A30S ribosomal protein S12 inhibitorEscherichia coli (strain K12) A16S ribosomal RNA inhibitorEnteric bacteria and other eubacteria - Absorption
Kanamycin is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Poor oral and topical absorption except with severe skin damage.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
2.5 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance. Oral LD50 is 17500 mg/kg in mice, over 4 g/kg in rats, and over 3 g/kg in rabbits.
- Pathways
Pathway Category Kanamycin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Kanamycin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Kanamycin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Kanamycin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Kanamycin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Kanamycin which could result in a higher serum level. Acetylcholine The therapeutic efficacy of Acetylcholine can be decreased when used in combination with Kanamycin. Acetyldigitoxin The risk or severity of adverse effects can be increased when Kanamycin is combined with Acetyldigitoxin. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Kanamycin which could result in a higher serum level. Acrivastine Acrivastine may decrease the excretion rate of Kanamycin which could result in a higher serum level. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Kanamycin sulfate J80EX28SMQ 25389-94-0 OOYGSFOGFJDDHP-KMCOLRRFSA-N - International/Other Brands
- Efficin (Lupin) / Kanamytrex (Alcon) / Kancin (Alembic) / Kancin-L (Atlantic) / Winamycin (Winston)
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Kanamycin Injection, solution 333 mg/1mL Intramuscular; Intravenous Fresenius Kabi USA, LLC 2003-01-28 2009-05-18 US 
Kantrex Injection, solution 1 g/3mL Intramuscular; Intraperitoneal; Intravenous; Irrigation; Respiratory (inhalation) E.R. Squibb & Sons, L.L.C. 2005-01-01 2006-09-30 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image KANCIN-L Kanamycin sulfate (1 G) + Lidocaine hydrochloride (20 mg/ml) Solution บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 1985-02-14 2020-06-11 Thailand 
Categories
- ATC Codes
- S01AA24 — KanamycinJ01GB04 — Kanamycin
- J01GB — Other aminoglycosides
- J01G — AMINOGLYCOSIDE ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Alimentary Tract and Metabolism
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiinfectives for Systemic Use
- Carbohydrates
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Enzyme Inhibitors
- Glycosides
- Intestinal Antiinfectives
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- Ophthalmologicals
- Protein Synthesis Inhibitors
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- 4,6-disubstituted 2-deoxystreptamines
- Alternative Parents
- O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / 1,2-aminoalcohols / Polyols / Oxacyclic compounds / Acetals show 4 more
- Substituents
- 1,2-aminoalcohol / 4,6-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives / Cyclohexanol show 16 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- kanamycins (CHEBI:17630)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- EQK9Q303C5
- CAS number
- 59-01-8
- InChI Key
- SBUJHOSQTJFQJX-NOAMYHISSA-N
- InChI
- 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
- IUPAC Name
- (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol
- SMILES
- NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
References
- Synthesis Reference
Hamao Umezawa, Shinichi Kondo, "Method for production of kanamycin C and its derivatives." U.S. Patent US4120955, issued December, 1975.
US4120955- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015303
- KEGG Compound
- C01822
- PubChem Compound
- 6032
- PubChem Substance
- 46508178
- ChemSpider
- 5810
- BindingDB
- 50031282
- 6099
- ChEBI
- 17630
- ChEMBL
- CHEMBL1384
- ZINC
- ZINC000008214590
- Therapeutic Targets Database
- DNC000201
- PharmGKB
- PA450137
- PDBe Ligand
- KAN
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Kanamycin_A
- PDB Entries
- 1kny / 1l8t / 1m4i / 1nd4 / 2esi / 3kp5 / 3q5r / 3sg9 / 3u6t / 4dfb … show 16 more
- MSDS
- Download (71.9 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Prevention Colorectal Neoplasms 1 3 Completed Treatment Multidrug Resistant Tuberculosis 1 2, 3 Completed Treatment Extensively Drug Resistant Tuberculosis / Multidrug Resistant Tuberculosis / Tuberculosis (TB) 1 1 Completed Other Tuberculosis (TB) 1 1 Completed Treatment Healthy Subjects (HS) 1 0 Terminated Treatment Osteomyelitis 1 Not Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections 1 Not Available Recruiting Not Available Tuberculosis (TB) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- APP Pharmaceuticals
- Bristol-Myers Squibb Co.
- Cardinal Health
- Gallipot
- Mead Johnson and Co.
- Dosage Forms
Form Route Strength Injection Parenteral Injection, solution Intramuscular; Intravenous 333 mg/1mL Capsule Injection Intramuscular; Intravenous Injection, powder, for solution Intramuscular 1 g/vial Injection, powder, for solution Intramuscular 2 g/vial Powder 500 mg/1vial Injection, powder, for solution Intramuscular 1 g Injection Intramuscular 1 g/3ml Suspension Oral 250 mg/5ml Solution 0.5 g Solution Injection, solution Intramuscular; Intraperitoneal; Intravenous; Irrigation; Respiratory (inhalation) 1 g/3mL Solution 250 mg/1ml Capsule 250 mg - Prices
Unit description Cost Unit Kanamycin sulfate powder 25.2USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -6.3 Not Available - Predicted Properties
Property Value Source Water Solubility 92.3 mg/mL ALOGPS logP -3.1 ALOGPS logP -7.1 Chemaxon logS -0.72 ALOGPS pKa (Strongest Acidic) 12.11 Chemaxon pKa (Strongest Basic) 9.54 Chemaxon Physiological Charge 4 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 11 Chemaxon Polar Surface Area 282.61 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 106.13 m3·mol-1 Chemaxon Polarizability 47.57 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9351 Blood Brain Barrier - 0.9815 Caco-2 permeable - 0.7545 P-glycoprotein substrate Substrate 0.5281 P-glycoprotein inhibitor I Non-inhibitor 0.7592 P-glycoprotein inhibitor II Non-inhibitor 0.904 Renal organic cation transporter Non-inhibitor 0.8353 CYP450 2C9 substrate Non-substrate 0.8325 CYP450 2D6 substrate Non-substrate 0.8323 CYP450 3A4 substrate Non-substrate 0.6719 CYP450 1A2 substrate Non-inhibitor 0.9143 CYP450 2C9 inhibitor Non-inhibitor 0.9259 CYP450 2D6 inhibitor Non-inhibitor 0.9317 CYP450 2C19 inhibitor Non-inhibitor 0.915 CYP450 3A4 inhibitor Non-inhibitor 0.97 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9261 Ames test Non AMES toxic 0.7406 Carcinogenicity Non-carcinogens 0.9488 Biodegradation Not ready biodegradable 0.849 Rat acute toxicity 1.5431 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9772 hERG inhibition (predictor II) Non-inhibitor 0.8151
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - DI-ESI-Ion Trap , Positive LC-MS/MS Not Available MS/MS Spectrum - DI-ESI-Hybrid FT , Positive LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Trna binding
- Specific Function
- With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
- Gene Name
- rpsL
- Uniprot ID
- P0A7S3
- Uniprot Name
- 30S ribosomal protein S12
- Molecular Weight
- 13736.995 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Stavropoulos TA, Strathdee CA: Synergy between tetA and rpsL provides high-stringency positive and negative selection in bacterial artificial chromosome vectors. Genomics. 2001 Feb 15;72(1):99-104. [Article]
- Gondo Y, Shioyama Y, Nakao K, Katsuki M: A novel positive detection system of in vivo mutations in rpsL (strA) transgenic mice. Mutat Res. 1996 May 17;360(1):1-14. [Article]
- Amanuma K, Takeda H, Amanuma H, Aoki Y: Transgenic zebrafish for detecting mutations caused by compounds in aquatic environments. Nat Biotechnol. 2000 Jan;18(1):62-5. [Article]
Yes
Inhibitor
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Roy U, Nair D: Biodiversity of organotin resistant Pseudomonas from west coast of India. Ecotoxicology. 2007 Mar;16(2):253-61. Epub 2006 Nov 28. [Article]
- Pikuta EV, Hoover RB, Bej AK, Marsic D, Whitman WB, Krader PE, Tang J: Trichococcus patagoniensis sp. nov., a facultative anaerobe that grows at -5 degrees C, isolated from penguin guano in Chilean Patagonia. Int J Syst Evol Microbiol. 2006 Sep;56(Pt 9):2055-62. [Article]
- Chung JH, Park YS, Kim J, Shin GW, Nam MH, Oh MK, Kim CW, Jung GY, Hyun Park J: Parallel analysis of antimicrobial activities in microbial community by SSCP based on CE. Electrophoresis. 2007 Jul;28(14):2416-23. [Article]
Enzymes
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
- Specific Function
- Aminoglycoside 2'-n-acetyltransferase activity
- Gene Name
- aac
- Uniprot ID
- P9WQG9
- Uniprot Name
- Aminoglycoside 2'-N-acetyltransferase
- Molecular Weight
- 20037.53 Da
References
- Vetting MW, Hegde SS, Javid-Majd F, Blanchard JS, Roderick SL: Aminoglycoside 2'-N-acetyltransferase from Mycobacterium tuberculosis in complex with coenzyme A and aminoglycoside substrates. Nat Struct Biol. 2002 Sep;9(9):653-8. [Article]
- Ramirez MS, Tolmasky ME: Aminoglycoside modifying enzymes. Drug Resist Updat. 2010 Dec;13(6):151-71. doi: 10.1016/j.drup.2010.08.003. Epub 2010 Sep 15. [Article]
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Nucleotidyltransferase activity
- Specific Function
- Inactivates the antibiotic kanamycin by catalyzing the transfer of a nucleotidyl group from nucleoside triphosphates such as ATP to the 4'-hydroxyl group of the aminoglycoside.
- Gene Name
- knt
- Uniprot ID
- P05057
- Uniprot Name
- Kanamycin nucleotidyltransferase
- Molecular Weight
- 28797.38 Da
References
- Gates CA, Northrop DB: Substrate specificities and structure-activity relationships for the nucleotidylation of antibiotics catalyzed by aminoglycoside nucleotidyltransferase 2''-I. Biochemistry. 1988 May 17;27(10):3820-5. [Article]
- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Kanamycin kinase activity
- Specific Function
- Resistance to kanamycin and structurally-related aminoglycosides, including amikacin.
- Gene Name
- aphA1
- Uniprot ID
- P00551
- Uniprot Name
- Aminoglycoside 3'-phosphotransferase
- Molecular Weight
- 30960.85 Da
References
- Wieninger SA, Serpersu EH, Ullmann GM: ATP binding enables broad antibiotic selectivity of aminoglycoside phosphotransferase(3')-IIIa: an elastic network analysis. J Mol Biol. 2011 Jun 10;409(3):450-65. doi: 10.1016/j.jmb.2011.03.061. Epub 2011 Apr 6. [Article]
- Thompson PR, Hughes DW, Wright GD: Mechanism of aminoglycoside 3'-phosphotransferase type IIIa: His188 is not a phosphate-accepting residue. Chem Biol. 1996 Sep;3(9):747-55. [Article]
- Menard R, Molinas C, Arthur M, Duval J, Courvalin P, Leclercq R: Overproduction of 3'-aminoglycoside phosphotransferase type I confers resistance to tobramycin in Escherichia coli. Antimicrob Agents Chemother. 1993 Jan;37(1):78-83. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:47