Basic information
- Standard SMILES
NC[C@@H]1O[C@H](O[C@H]2[C@@H](O)[C@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)O[C@@H]2CO)[C@H](N)[C@@H](O)[C@@H]1O.O=S(=O)(O)O- InChIKey
OIXVKQDWLFHVGR-WQDIDPJDSA-N- Molecular formula
- C23H48N6O17S
- Average molar mass
- 712.7 g/mol
- Monoisotopic mass
- 712.27966508
Overview
Neomycin B sulfate is the aminoglycoside sulfate salt that is the sulfate salt of neomycin B; a component of neomycin sulfate. It contains a framycetin.
Names & identifiers
- Preferred name
- Neomycin Sulfate
- IUPAC
- (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol;sulfuric acid
- English name
- neomycin B sulphate
- Molecular formula
- C23H48N6O17S
- Molecular weight
- 712.72
Names & synonyms
Show more names
Database identifiers
- CAS
1405-10-3、25389-98-4、28002-70-2、4146-30-9- PubChem CID
- 197162
- DTXSID
DTXSID10948247- ChEMBL
CHEMBL1950493- ChEBI
CHEBI:53636- EC Number
- 215-773-1、248-770-9
Properties
Computed structural properties
- Topological polar surface area
- 436 Ų
- Hydrogen bond donors
- 15
- Hydrogen bond acceptors
- 23
- Rotatable bonds
- 9
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 953
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Aminoglycosides; Dermatologic Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- storage temp.
- -20 °C · -20°C
- form
- solid
- Major Application
- USP Biologicspharmaceutical
- InChIKey
- OIXVKQDWLFHVGR-WQDIDPJDSA-N
- FDA UNII
- 3720 KZ4TQ · Y3720KZ4TQ
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317
- Precautionary statements
- 261 · P261-P272-P280-P302+P352-P333+P313-P362+P364
- WGK Germany
- 3 · WGK 3
- Storage Class
- 13 · 13 - Non Combustible Solids
- Hazard Classifications
- 1 · Skin Sens. 1
Safety & regulation
GHS classification
GHS Classification
Danger
H317 (95.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P233, P260, P261, P271, P272, P273, P280, P284, P302+P352, P304+P340, P318, P319, P321, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 372 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 96.3% (52 of 54) of all reports.
Not Classified
Hazard information
Regulatory Information
Hazard Traits - Developmental Toxicity
Neomycin sulphate: Does not have an individual approval but may be used under an appropriate group standard
Framycetin sulfate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Not Classified
Skin Sens. 1 (95.7%)
Acute Tox. 4 (15.4%)
Toxicology
Exposure Routes
Eye contact; topical (eye drops). Poorly absorbed from the normal gastrointestinal tract. Although only approximately 3% of neomycin is absorbed through intact intestinal mucosa, significant amounts may be absorbed through ulcerated or denuded mucosa or if inflammation is present.
Toxicity Summary
Aminoglycosides like neomycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically neomycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Neomycin sulfate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P362+P364
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Neomycin undergoes negligible biotransformation after parenteral administration. Route of Elimination: The small absorbed fraction is rapidly distributed in the tissues and is excreted by the kidney in keeping with the degree of kidney function. Half Life: 2 to 3 hours
FDA Pharmacological Classification
FIRST AID OINTMENT
Aminoglycoside Antibacterial [EPC]; Aminoglycosides [CS]
NEOMYCIN SULFATE
Aminoglycoside Antibacterial [EPC]; Aminoglycosides [CS]
NEOMYCIN OINTMENT
Aminoglycoside Antibacterial [EPC]; Aminoglycosides [CS]
MeSH Pharmacological Classification
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
Uses
Topical uses include treatment for superficial eye infections caused by susceptible bacteria (used in combination with other antiinfectives), treatment of otitis externa caused by susceptible bacteria, treatment or prevention of bacterial infections in skin lesions, and use as a continuous short-term irrigant or rinse to prevent bacteriuria and gram negative rod bacteremia in abacteriuric patients with indwelling catheters. May be used orally to treat hepatic encephalopathy, as a perioperative prophylactic agent, and as an adjunct to fluid and electrolyte replacement in the treatment of diarrhea caused to enteropathogenic E. coli (EPEC).
Applications
UsesNeomycin B Trisulfate is a trisulfate salt analog of Neomycin B (N389983), which is an aminoglycoside antibiotic.
Suppliers8 total
Additional notes
DefinitionChEBI: Neomycin B sulfate is the aminoglycoside sulfate salt that is the sulfate salt of neomycin B; a component of neomycin sulfate. It contains a framycetin.
Related reactions
Linked notes
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