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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL177
CHEMBL177
Compound Name AMIKACIN
ChEMBL Synonyms AMIKACIN | Amikin | BB-K8 | AMIKACIN SULFATE | Amiglyde | AMIKIN
Max Phase 4 (Approved)
Trade Names Amiglyde | AMIKACIN SULFATE | AMIKIN
Molecular Formula C22H43N5O13

Additional synonyms for CHEMBL177 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@ ...
Download SMILES
Standard InChI InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22 ...
Download InChI
Standard InChI Key LKCWBDHBTVXHDL-RMDFUYIESA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL177

Molecule Features

CHEMBL177 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial 70S ribosome inhibitor Bacterial 70S ribosome PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
InfectionD007239EFO:0000544infection4DailyMed
DailyMed
DailyMed
ClinicalTrials
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
ClinicalTrials
Pneumonia, BacterialD018410EFO:1001272bacterial pneumonia3ClinicalTrials
ClinicalTrials
PneumoniaD011014EFO:0003106pneumonia2ClinicalTrials
Pulmonary Disease, Chronic ObstructiveD029424EFO:0000341chronic obstructive pulmonary disease0ClinicalTrials
Urinary Tract InfectionsD014552EFO:0003103urinary tract infection4DailyMed
DailyMed
DailyMed
Lung DiseasesD008171EFO:0003818lung disease2ClinicalTrials
Pneumonia, Ventilator-AssociatedD053717EFO:1001865ventilator-associated pneumonia3ClinicalTrials
Intraabdominal InfectionsD0594134DailyMed
DailyMed
DailyMed
PeritonitisD0105384DailyMed
DailyMed
DailyMed
Staphylococcal InfectionsD013203EFO:0005681Staphylococcus aureus infection4DailyMed
DailyMed
Cystic FibrosisD003550Orphanet:586Cystic fibrosis3ClinicalTrials
MeningitisD008581EFO:0000584infectious meningitis4DailyMed
DailyMed
DailyMed
SepsisD018805HP:0100806sepsis4DailyMed
DailyMed
DailyMed

Clinical Data

ClinicalTrials.gov AMIKACIN
The Cochrane Collaboration AMIKACIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
585.6 585.2857 -8.42 10 331.94 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
17 13 3 18 17 3


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
12.94 9.52 -5.26 -10.59 0 40 0.11

Structural Alerts

There are 4 structural alerts for CHEMBL177. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D06 - ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D06A - ANTIBIOTICS FOR TOPICAL USE
D06AX - Other antibiotics for topical use
D06AX12 - amikacin

S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AA - Antibiotics
S01AA21 - amikacin

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01G - AMINOGLYCOSIDE ANTIBACTERIALS
J01GB - Other aminoglycosides
J01GB06 - amikacin

ChemSpider ChemSpider:LKCWBDHBTVXHDL-RMDFUYIESA-N
DailyMed amikacin sulfate
PubChem SID: 144204752 SID: 170465345 SID: 29215141
Wikipedia Amikacin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL177



ACToR 37517-28-5 108914-65-4
Brenda 1394
ChEBI 2637
ChemicalBook CB8146049
DrugBank DB00479
DrugCentral 157
eMolecules 36519241
EPA CompTox Dashboard DTXSID3022586
FDA SRS 84319SGC3C
Human Metabolome Database HMDB0014622
IBM Patent System 57B6E10FDDEB2E4DE48A76F531E57F91
KEGG Ligand C06820
LINCS LSM-5935
Mcule MCULE-6148260173
MolPort MolPort-000-761-900
Nikkaji J19.345C
PDBe AKN
PharmGKB PA164744372
PubChem 37768
PubChem: Thomson Pharma 14886882
SureChEMBL SCHEMBL2985
ZINC ZINC000008214483

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/LKCWBDHBTVXHDL-RMDFUYIESA-N spacer
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