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Compound Detail

CHEMBL1747

TOBRAMYCIN
💊 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](N)C[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1747
Name TOBRAMYCIN
Phase Approved
Structure Type MOL
InChI Key NLVFBUXFDBBNBW-PBSUHMDJSA-N
Therapeutic ✓ Yes

Known Names

47663 Aktob Bethkis Bramitob Kitabis pak Nebcin Nebicin Nebramycin factor 6 Nebramycin vi Nebris NSC-180514 Tobi +14 more
9
Targets
24
Activities
3
Assay Types
30
PK Parameters
20
Publications
26
Known Names
20
Indications
1
Mechanisms

Molecular Properties

467.5
MW (Da)
-6.30
ALogP
14
HBA
10
HBD
268.2
PSA (Ų)
0.17
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -mycin
USAN Year 1972

Extended Properties

Molecular Formula C18H37N5O9
MW 467.52
Aromatic Rings 0
Heavy Atoms 32
NP-Likeness 1.43

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
70S ribosome inhibitor INHIBITOR 70S ribosome ✓ ✓

Indications

Bacterial Infections Conjunctivitis, Allergic Cystic Fibrosis Eye Infections Infections Inflammation Respiratory Tract Infections Blepharitis Cataract Conjunctivitis, Bacterial Fractures, Bone Pneumonia Pseudomonas Infections Bronchiectasis Pneumonia, Bacterial Bronchopulmonary Dysplasia Dry Eye Syndromes Renal Insufficiency, Chronic Sinusitis Diabetic Foot

ATC Classification

J01GB01
tobramycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA12
tobramycin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
nephrotoxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

Kd 19 meas. best 9.05
IC50 4 meas. best 8.21
Ki 1 meas. best 4.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
No relevant target
CHEMBL2362975
 Kd 9.05 9.05 0.9 1
Unchecked
CHEMBL612545
 IC50 8.21 6.29 6.2 2
Escherichia coli
CHEMBL354
 IC50 7.82 7.82 15.0 1
Ribosomal RNA A-site
CHEMBL614640
 IC50 7.16 7.16 70.0 1
Nucleic Acid
CHEMBL345
 Kd 7.1 5.8582 80.0 11
Ribosomal RNA A-site
CHEMBL614640
 Kd 5.82 5.82 1500.0 1
Unchecked
CHEMBL612545
 Kd 5.78 5.78 1680.0 1
Human immunodeficiency virus type 1 REV
CHEMBL3852
 Kd 5.39 5.39 4110.0 1
i-motif DNA
CHEMBL4845622
 Kd 4.89 4.83 13000.0 2
dsDNA
CHEMBL3832741
 Kd 4.75 4.75 18000.0 1
Bacillus subtilis
CHEMBL359
 Kd 4.42 4.42 38000.0 1
Unchecked
CHEMBL612545
 Ki 4.22 4.22 59900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 273.83 ng.hr.mL-1 Mus musculus
AUC 315.67 ng.hr.mL-1 Mus musculus
AUC 10978.17 ng.hr.mL-1 Mus musculus
AUC 11117.0 ng.hr.mL-1 Mus musculus
AUC 11382.17 ng.hr.mL-1 Mus musculus
AUC 11457.83 ng.hr.mL-1 Mus musculus
AUC 7061.33 ng.hr.mL-1 Mus musculus
AUC 7296.67 ng.hr.mL-1 Mus musculus
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 0.98 mL.min-1.kg-1 Homo sapiens
Cmax 705.85 nM Mus musculus
Cmax 35207.05 nM Mus musculus
Cmax 75419.23 nM Mus musculus
Cmax 16683.78 nM Mus musculus
Cmax 9839.15 nM Homo sapiens
Cmax 11122.52 nM Homo sapiens
Excretion 90.0 % Homo sapiens
F 0.48 % Mus musculus
F 96.45 % Mus musculus
F 100.0 % Mus musculus
F 12.4 % Mus musculus
F 9.0 % Homo sapiens
Fu 1.0 - Homo sapiens
MRT 2.4 hr Homo sapiens
T1/2 0.55 hr Mus musculus
T1/2 0.6935 hr Mus musculus
T1/2 0.295 hr Mus musculus
T1/2 0.3388 hr Mus musculus
T1/2 0.3662 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
No relevant target Kd = 0.9 nM 9.05 Dissociation constant of the compound 15293991
Unchecked IC50 = 6.2 nM 8.21 Inhibition of circular DNA translation in Escherichia coli S30 extract after 60 ... 27524179
Escherichia coli IC50 = 15.0 nM 7.82 Inhibition of protein synthesis in Escherichia coli S30 extracts after 90 mins b... 23786357
Ribosomal RNA A-site IC50 = 70.0 nM 7.16 Binding affinity to 16S rRNA A-site in Escherichia coli S30 extract assessed as ... 27509271
Nucleic Acid Kd = 80.0 nM 7.1 Binding affinity to A-site RNA 19445516
Nucleic Acid Kd = 430.0 nM 6.37 Dissociation constant for binding to mitochondrial 12S rRNA construct M3 was det... 12127547
Nucleic Acid Kd = 680.0 nM 6.17 Tested for binding affinity against RNA construct E 11814798
Ribosomal RNA A-site Kd = 1500.0 nM 5.82 Binding affinity of aminoglycoside to 16S ribosomal RNA A-site in Escherichia co... 11206440
Nucleic Acid Kd = 1680.0 nM 5.78 Dissociation constant towards 16S rRNA construct B 10915059
Unchecked Kd = 1680.0 nM 5.78 Dissociation constant with dimeric 16S rRNA RNA construct B 11677142
Nucleic Acid Kd = 2040.0 nM 5.69 Tested for binding affinity against RNA construct B 11814798
Nucleic Acid Kd = 2070.0 nM 5.68 Tested for binding affinity against RNA construct A 11814798
Nucleic Acid Kd = 2110.0 nM 5.68 Dissociation constant towards 16S rRNA construct A 10915059
Nucleic Acid Kd = 2120.0 nM 5.67 Tested for binding affinity against RNA construct D 11814798
Nucleic Acid Kd = 2910.0 nM 5.54 Dissociation constant for binding to mitochondrial 12S rRNA construct M4 was det... 12127547
Nucleic Acid Kd = 3260.0 nM 5.49 Dissociation constant for binding to mitochondrial 12S rRNA construct M2 was det... 12127547
Human immunodeficiency virus type 1 REV Kd = 4110.0 nM 5.39 Tested for the ability to bind the HIV-1 RRE-RNA construct by fluorescence aniso... 11354359
Nucleic Acid Kd = 5370.0 nM 5.27 Dissociation constant for binding to mitochondrial 12S rRNA construct M5 was det... 12127547
i-motif DNA Kd = 13000.0 nM 4.89 Binding affinity to human c-Myc promoter i-motif DNA by SPR analysis 35835380
i-motif DNA Kd = 17000.0 nM 4.77 Binding affinity to human telomeric i-motif DNA by SPR analysis 35835380

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 344
19805554 10.1128/aac.00248-09 Pseudomonas aeruginosa 71
31022550 10.1016/j.ejmech.2019.04.034 Pseudomonas aeruginosa 55
18591275 10.1128/aac.01684-07 Acinetobacter baumannii 40
17261619 10.1128/aac.01278-06 Pseudomonas aeruginosa 38
19188376 10.1128/aac.01264-08 Pseudomonas aeruginosa 33
33848161 10.1021/acs.jnatprod.0c01151 Pseudomonas aeruginosa 33
20194693 10.1128/aac.00816-09 Pseudomonas aeruginosa 32
27524179 10.1021/acs.jmedchem.6b00867 Pseudomonas aeruginosa 28
19258280 10.1128/aac.01024-08 Pseudomonas aeruginosa 28
20921306 10.1128/aac.00598-10 Acinetobacter lwoffii 26
- 10.1039/C5MD00373C Pseudomonas aeruginosa 24
20086144 10.1128/aac.01172-09 Mus musculus 24
19332676 10.1128/aac.00428-08 Pseudomonas aeruginosa 23
17194835 10.1128/aac.00704-06 Pseudomonas aeruginosa 21
18490506 10.1128/aac.01634-07 Klebsiella pneumoniae 20
15808482 10.1016/j.bmcl.2005.02.029 Pseudomonas aeruginosa 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19917762 10.1128/aac.00912-09 Pseudomonas aeruginosa 18
19015360 10.1128/aac.00883-08 Klebsiella pneumoniae 18

Data from ChEMBL 36 via Core Engine