Chemical Component Summary

NameArbekacin
Synonyms(2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide
Identifiers(2~{S})-~{N}-[(1~{R},2~{S},3~{S},4~{R},5~{S})-4-[(2~{R},3~{R},6~{S})-6-(aminomethyl)-3-azanyl-oxan-2-yl]oxy-5-azanyl-2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide
FormulaC22 H44 N6 O10
Molecular Weight552.619
TypeNON-POLYMER
Isomeric SMILESC1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)NC(=O)[C@H](CCN)O)N)N
InChIInChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1
InChIKeyMKKYBZZTJQGVCD-XTCKQBCOSA-N

Chemical Details

Formal Charge0
Atom Count82
Chiral Atom Count14
Bond Count84
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB06696 
NameArbekacin
Groups
  • investigational
  • experimental
DescriptionAn semisynthetic aminoglycoside antibiotic. Often used for treatment of multi-resistant bacterial infection such as methicillin-resistant _Staphylococcus aureus_ (MRSA).
Synonyms
  • Arbekacine
  • Arbekacina
  • Arbekacin sulfate
  • Haberacin
  • Arbekacinum
IndicationArbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant <i>Staphylococcus aureus</i> (MRSA).
Categories
  • Agents that produce neuromuscular block (indirect)
  • Aminoglycoside Antibacterials
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-CodeJ01GB12
CAS number51025-85-5

Drug Targets

NameTarget SequencePharmacological ActionActions
30S ribosomal protein S12MATVNQLVRKPRARKVAKSNVPALEACPQKRGVCTRVYTTTPKKPNSALR...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 68682
ChEMBL CHEMBL426926
ChEBI CHEBI:37922