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Compound Detail

CHEMBL1384

KANAMYCIN
💊 Approved Drug
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💊 Approved Drug
NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](O)[C@@H](O)[C@@H]1O

Basic Information

ChEMBL ID CHEMBL1384
Name KANAMYCIN
Phase Approved
Structure Type MOL
InChI Key SBUJHOSQTJFQJX-NOAMYHISSA-N
Therapeutic ✓ Yes

Known Names

Kanamicina Kanamycin Kanamycine Kanamycins
14
Targets
30
Activities
3
Assay Types
4
PK Parameters
20
Publications
4
Known Names
5
Indications

Molecular Properties

484.5
MW (Da)
-7.29
ALogP
15
HBA
11
HBD
282.6
PSA (Ų)
0.17
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1973
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -mycin

Extended Properties

Molecular Formula C18H36N4O11
MW 484.50
Aromatic Rings 0
Heavy Atoms 33
NP-Likeness 1.56

Indications

Bacterial Infections Eye Infections Tuberculosis Tuberculosis, Multidrug-Resistant Osteomyelitis

ATC Classification

A07AA08
kanamycin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
J01GB04
kanamycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA24
kanamycin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 20 meas. best 7.52
EC50 5 meas. best 5.09
Kd 5 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Escherichia coli
CHEMBL354
IC50 7.52 6.902 30.0 5
Pseudomonas aeruginosa
CHEMBL348
IC50 7.31 7.31 49.0 1
Unchecked
CHEMBL612545
IC50 7.1 5.745 80.0 4
Ribosomal RNA A-site
CHEMBL614640
IC50 7.0 7.0 100.0 1
microRNA 21
CHEMBL1615322
Kd 7.0 7.0 100.0 1
Bacillus subtilis
CHEMBL359
IC50 6.87 6.87 135.0 1
Staphylococcus aureus
CHEMBL352
IC50 6.52 6.52 300.0 1
microRNA 21
CHEMBL1615322
IC50 5.96 5.96 1102.0 1
Nucleic Acid
CHEMBL345
Kd 5.68 5.3975 2080.0 4
Beta-ketoacyl-[acyl-carrier-protein] synthase III
CHEMBL4914
IC50 5.17 5.17 6800.0 1
Staphylococcus aureus
CHEMBL352
EC50 5.09 5.09 8200.0 1
Gap junction beta-2 protein
CHEMBL4295738
IC50 5.03 4.985 9400.0 2
Acinetobacter baumannii
CHEMBL614425
EC50 4.8 4.8 16000.0 1
Pseudomonas aeruginosa
CHEMBL348
EC50 4.6 4.6 25000.0 1
Enterobacter cloacae
CHEMBL349
EC50 4.43 4.43 37000.0 1
Klebsiella pneumoniae subsp. pneumoniae
CHEMBL613207
EC50 4.35 4.35 45000.0 1
Gap junction alpha-1 protein
CHEMBL4680024
IC50 4.32 4.32 48000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.4 mL.min-1.kg-1 Homo sapiens
Fu 0.99 - Homo sapiens
MRT 3.1 hr Homo sapiens
T1/2 2.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Escherichia coli IC50 = 30.0 nM 7.52 Inhibition of protein translation in Escherichia coli S30 cell extract using cir... 28343755
Escherichia coli IC50 = 40.0 nM 7.4 Inhibition of cell free transcription/translation by Escherichia coli s30 bacter... 12139453
Pseudomonas aeruginosa IC50 = 49.0 nM 7.31 Antibacterial activity against Pseudomonas aeruginosa NCIM 2036 after 8 hrs by s... 29738954
Unchecked IC50 = 80.0 nM 7.1 In vitro inhibition of translation in luciferase SP6 control plasmid 12139453
microRNA 21 Kd = 100.0 nM 7.0 Binding affinity to biotinylated pre-miRNA-21 (unknown origin) by SPR analysis 31098005
Ribosomal RNA A-site IC50 = 100.0 nM 7.0 Binding affinity to 16S rRNA A-site in Escherichia coli S30 extract assessed as ... 27509271
Bacillus subtilis IC50 = 135.0 nM 6.87 Antibacterial activity against Bacillus subtilis NCIM 2079 after 12 hrs by seria... 29738954
Escherichia coli IC50 = 162.0 nM 6.79 Antibacterial activity against Escherichia coli NCIM 2688 after 8 hrs by serial ... 29738954
Staphylococcus aureus IC50 = 300.0 nM 6.52 Antibacterial activity against Staphylococcus aureus NCIM 2010 after 12 hrs by s... 29738954
Escherichia coli IC50 = 400.0 nM 6.4 Inhibition of protein synthesis in Escherichia coli S30 extracts by coupled tran... 16890435
Escherichia coli IC50 = 400.0 nM 6.4 Inhibition of protein synthesis in Escherichia coli by coupled transcription-tra... 17188860
microRNA 21 IC50 = 1102.0 nM 5.96 Displacement of F-neo from premature miRNA21 (unknown origin) by fluorescence as... 30109002
Nucleic Acid Kd = 2080.0 nM 5.68 Dissociation constant for binding to mitochondrial 12S rRNA construct M3 was det... 12127547
Nucleic Acid Kd = 2640.0 nM 5.58 Dissociation constant for binding to mitochondrial 12S rRNA construct M5 was det... 12127547
Unchecked IC50 = 3100.0 nM 5.51 Inhibition of Escherichia coli FabH expressed in Escherichia coli BL21 (DE3) aft... 24594526
Nucleic Acid Kd = 3460.0 nM 5.46 Dissociation constant for binding to mitochondrial 12S rRNA construct M2 was det... 12127547
Unchecked IC50 = 6300.0 nM 5.2 Inhibition of Escherichia coli FabH overexpressed in Escherichia coli DH10B usin... 23770447
Unchecked IC50 = 6700.0 nM 5.17 Inhibition of Pseudomonas aeruginosa FabH after 25 mins 24594526
Beta-ketoacyl-[acyl-carrier-protein] synthase III IC50 = 6800.0 nM 5.17 Inhibition of Escherichia coli FabH 25318998
Staphylococcus aureus EC50 = 8200.0 nM 5.09 Antibacterial activity against multidrug resistant Staphylococcus aureus subsp. ... 27184767

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 295
17923494 10.1128/aac.00328-07 Staphylococcus aureus 73
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44
17194835 10.1128/aac.00704-06 Pseudomonas aeruginosa 21
20211889 10.1128/aac.01677-09 Escherichia coli 20
19029325 10.1128/aac.00754-08 Enterococcus faecalis 18
19223646 10.1128/aac.01087-08 Escherichia coli 18
24997576 10.1016/j.bmc.2014.06.012 Mycolicibacterium smegmatis 17
28343755 10.1016/j.bmc.2017.02.068 Escherichia coli 17
17353252 10.1128/aac.01551-06 Mycobacteroides abscessus 17
20876376 10.1128/aac.00719-10 Escherichia coli 16
17060530 10.1128/aac.00261-06 Bifidobacterium longum 15
19752278 10.1128/aac.00631-09 Serratia marcescens 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
25556094 10.1016/j.bmcl.2014.12.029 Staphylococcus aureus 12
25556094 10.1016/j.bmcl.2014.12.029 Escherichia coli 12
20713679 10.1128/aac.00661-10 Mycobacterium tuberculosis 12
31176094 10.1016/j.ejmech.2019.05.081 Mycolicibacterium smegmatis 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20498323 10.1128/aac.01803-09 Burkholderia pseudomallei 10

Data from ChEMBL 36 via Core Engine