CNY

13,15-DIAMINO-2-(AMINOMETHYL)-3,4,9,12-TETRAHYDROXYHEXADECAHYDRO-2H-7,10-EPOXYPYRANO[2,3-B][1,10,4]BENZODIOXAZACYCLODODECIN-8-YL 2,6-DIAMINO-2,6-DIDEOXYHEXOPYRANOSIDE



Chemical Component Summary

Name13,15-DIAMINO-2-(AMINOMETHYL)-3,4,9,12-TETRAHYDROXYHEXADECAHYDRO-2H-7,10-EPOXYPYRANO[2,3-B][1,10,4]BENZODIOXAZACYCLODODECIN-8-YL 2,6-DIAMINO-2,6-DIDEOXYHEXOPYRANOSIDE
SynonymsCYCLIC NEOMYCIN
Identifiersn/a
FormulaC23 H44 N6 O12
Molecular Weight596.628
TypeNON-POLYMER
Isomeric SMILESC1[C@H]([C@@H]([C@@H]2[C@@H]([C@H]1N)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)NC[C@@H]4[C@H]([C@H]([C@@H](O4)O2)O)O[C@@H]5[C@@H]([C@H]([C@@H]([C@@H](O5)CN)O)O)N)O)N
InChIInChI=1S/C23H44N6O12/c24-2-7-13(31)15(33)10(28)21(36-7)40-19-9-4-29-11-16(34)14(32)8(3-25)37-22(11)39-18-6(27)1-5(26)12(30)20(18)41-23(38-9)17(19)35/h5-23,29-35H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
InChIKeyDXIORKRGAWCDSD-LSWIJEOBSA-N

Chemical Details

Formal Charge0
Atom Count85
Chiral Atom Count19
Bond Count89
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00994 
NameNeomycin
Groups
  • vet_approved
  • approved
DescriptionNeomycin is a broad-spectrum aminoglycoside antibiotic drug that is derived from the metabolic products of _Streptomyces fradiae_.[L11979] Neomycin is a complex comprised of three components, neomycin A, B, and C.[A191529] Neomycin B, also known as [framycetin], is the most active component of the complex and neomycin C is the isomer of neomycin B, making these two stereoisomers the active components of neomycin.[A175042,A191529] Neomycin A, or [neamine], is a moiety that conjoins two molecules of neomycin B and C together.[A175042] Neomycin is active against both gram-positive and gram-negative organisms and mediates its pharmacological action by binding to bacterial ribosomes and inhibiting protein synthesis, which is crucial for the survival of bacteria.[L11985] Neomycin sulfate is the most common form for pharmaceutical preparations; because the compound is a complex, the amount of neomycin in products is measured in units.[A191529] Neomycin sulfate as monotherapy is available in an oral solution for adjunct use in the treatment of hepatic coma.[L11979] It is also used in combination with [polymyxin B] sulfates and [hydrocortisone] in otic suspensions for use in the treatment of bacterial infections in the external auditory canal, including infections caused by medical procedures in the ear.[L10532] Neomycin is also used in combination with [polymyxin B] sulfates and [dexamethasone] in ophthalmic preparations for use in the treatment of inflammatory conditions and infections in the eye.[L10716] Neomycin is also available in over-the-counter topical products to prevent minor skin infections.
Synonyms
  • Vonamycin
  • Neomicina
  • Kaomycine
  • Neomycin palmitate
  • Neomycin sulfate
Brand Names
  • Rite Aid Pharmacy Antibiotic With Pain Relief
  • 50 Person ANSI
  • Neosporin Kids Plus Pain Relief
  • DG Health Triple Antibiotic
  • Equate First Aid Antibiotic Pain Relieving
IndicationOral neomycin sulfate is indicated as an adjunctive therapy in hepatic coma (portal-system encephalopathy) by reducing ammonia-forming bacteria in the intestinal tract. It is strongly recommended that oral neomycin is only used in infections that are proven or strongly suspected to be caused by susceptible bacteria to reduce the risk of the development of drug-resistant bacteria.[L11979] Neomycin, in combination with polymyxin B sulfates and hydrocortisone in otic suspensions, is used in the treatment of superficial bacterial infections of the external auditory canal caused by organisms susceptible to the antibiotics. This otic formulation is also used in the treatment of infections of mastoidectomy and fenestration cavities caused by organisms susceptible to the antibiotics.[L10532] The ophthalmic solution containing neomycin in combination with polymyxin B sulfates and dexamethasone is used to treat steroid-responsive inflammatory ocular conditions for which a corticosteroid is indicated and where bacterial infection or a risk of bacterial infection exists.[L10716]
Categories
  • Agents that produce neuromuscular block (indirect)
  • Alimentary Tract and Metabolism
  • Aminoglycoside Antibacterials
  • Anti-Bacterial Agents
  • Anti-Infective Agents
ATC-Code
  • A07AA51
  • R02AB01
  • J01GB05
  • D06AX04
  • S03AA01
CAS number1404-04-2

Drug Targets

NameTarget SequencePharmacological ActionActions
30S ribosomal protein S12MATVNQLVRKPRARKVAKSNVPALEACPQKRGVCTRVYTTTPKKPNSALR...unknowninhibitor
16S ribosomal RNA-unknowninhibitor
Extracellular calcium-sensing receptorMAFYSCCWVLLALTWHTSAYGPDQRAQKKGDIILGGLFPIHFGVAAKDQD...unknown
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 5287961