Compound Detail
CHEMBL177
AMIKACIN 💊 Approved Drug
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💊 Approved Drug
NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
Basic Information
| ChEMBL ID | CHEMBL177 |
| Name | AMIKACIN |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | LKCWBDHBTVXHDL-RMDFUYIESA-N |
| Therapeutic | ✓ Yes |
4
Targets
15
Activities
3
Assay Types
9
PK Parameters
20
Publications
8
Known Names
12
Indications
Molecular Properties
585.6
MW (Da)
-8.42
ALogP
17
HBA
13
HBD
331.9
PSA (Ų)
0.11
QED
3
Ro5 Violations
10
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1981 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Indications
Bacterial Infections Eye Infections Cystic Fibrosis Mycobacterium Infections Pneumonia, Bacterial Pneumonia, Ventilator-Associated Lung Diseases Pneumonia Tuberculosis Osteomyelitis Pulmonary Disease, Chronic Obstructive Urinary Tract Infections
ATC Classification
D06AX12
amikacin
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
J01GB06
amikacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA21
amikacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
Drug Warnings
Black Box Warning
General Warning
Activity Summary
IC50 10 meas. best 7.16
EC50 3 meas. best 7.16
Kd 2 meas. best 7.3
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Nucleic Acid CHEMBL345 | Kd | 7.3 | 7.3 | 50.0 | 1 |
| Mycobacterium tuberculosis CHEMBL360 | EC50 | 7.16 | 7.08 | 70.0 | 3 |
| Mycobacterium tuberculosis CHEMBL360 | IC50 | 7.16 | 7.1217 | 70.0 | 6 |
| Ribosomal RNA A-site CHEMBL614640 | IC50 | 7.16 | 7.16 | 70.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 6.8 | 5.66 | 160.0 | 3 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 1.1 | mL.min-1.kg-1 | Homo sapiens |
| Cmax | 1844.23 | nM | Homo sapiens |
| Cmax | 60962.07 | nM | Homo sapiens |
| Cmax | 853.81 | nM | Homo sapiens |
| Cmax | 341.52 | nM | Homo sapiens |
| Fu | 0.88 | - | Homo sapiens |
| MRT | 2.4 | hr | Homo sapiens |
| T1/2 | 2.4 | hr | Homo sapiens |
| T1/2 | 0.58 | hr | Oryctolagus cuniculus |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL3885881 | Rattus norvegicus | 621 |
| 17261619 | 10.1128/aac.01278-06 | Pseudomonas aeruginosa | 98 |
| 19805565 | 10.1128/aac.01099-09 | Klebsiella pneumoniae | 40 |
| 18591275 | 10.1128/aac.01684-07 | Acinetobacter baumannii | 40 |
| 20194693 | 10.1128/aac.00816-09 | Pseudomonas aeruginosa | 32 |
| 19258280 | 10.1128/aac.01024-08 | Pseudomonas aeruginosa | 32 |
| 27073054 | 10.1016/j.bmc.2016.03.060 | Staphylococcus aureus | 32 |
| 18809945 | 10.1128/aac.00707-08 | Pseudomonas aeruginosa | 29 |
| 17846127 | 10.1128/aac.01259-06 | Acinetobacter baumannii | 26 |
| 17724156 | 10.1128/aac.01512-06 | Acinetobacter baumannii | 23 |
| 17043119 | 10.1128/aac.00892-06 | Escherichia coli | 23 |
| 28574259 | 10.1021/acs.jmedchem.7b00582 | Mycobacteroides abscessus | 22 |
| 17194835 | 10.1128/aac.00704-06 | Pseudomonas aeruginosa | 21 |
| 20350950 | 10.1128/aac.01818-09 | Klebsiella pneumoniae | 20 |
| 20231393 | 10.1128/aac.01359-09 | Escherichia coli | 19 |
| 15808482 | 10.1016/j.bmcl.2005.02.029 | Pseudomonas aeruginosa | 17 |
| 17682106 | 10.1128/aac.00503-07 | Pseudomonas aeruginosa | 17 |
| 17353252 | 10.1128/aac.01551-06 | Mycobacteroides abscessus | 17 |
| 18519713 | 10.1128/aac.01341-07 | Enterobacter cloacae | 16 |
| 20498315 | 10.1128/aac.00080-10 | Pseudomonas aeruginosa | 16 |
Data from ChEMBL 36 via Core Engine