Neomycin Sulfate

HCID 197162CAS 1405-10-3

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

NEOMYCIN SULFATENeomycin B sulfate1405-10-3Neomycin sulphateMycifradinBykomycinNeomixNeomycin, sulfate (salt)Fradiomycin sulfateNeo-RxMyciguentNeobiotic
Show more names
Framycin sulfateneomycin B sulphateChlorotoluron Impurity 5Neomycin B Sulfate (Framycetin Sulfate)2nd International Standard for Neomycin BFramycetin sulfate (Neomycin B sulfate) RS(2S,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((2R,3S,4R,5S)-5-(((1R,2R,3S,5R,6S)-3,5-diamino-2-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-hydroxycyclohexyl)(2S,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((2R,3S,4R,5S)-5-(((1R,2R,3S,5R,6S)-3,5-diamino-2-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-hydroxycyclohexyl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)tetrahydro-2H-pyran-3,4-diol xsulfate
Neo-FradinCHEBI:53636DTXSID10948247USAF CB-19TuttomycinEndomixinFraquinolMyacine

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

Experimental & physicochemical properties

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Aminoglycosides; Dermatologic Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsActive Ingredients (Neomycin Sulfate) -> FDA Greenbook

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 3 items

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.

Other Safety InformationIMAP assessments - Neomycin, sulfate (salt): Human health tier I assessment
Hazard Classes and Categories · 3 items

Not Classified

Skin Sens. 1 (95.7%)

Acute Tox. 4 (15.4%)

Toxicology

TreatmentHemodialysis will remove neomycin sulfate from the blood. (L1712)
Health EffectsAntibiotic resistance
Exposure Routes · 1 item

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 · 1 item

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.

Signs and SymptomsVestibular toxicity may result in vertigo, nausea and vomiting, dizziness and loss of balance.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

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

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 · 6 items

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 · 2 items

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 · 1 item

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).

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
General Manufacturing InformationNeomycin, sulfate (salt): ACTIVE

Applications

UsesNeomycin B Trisulfate is a trisulfate salt analog of Neomycin B (N389983), which is an aminoglycoside antibiotic.

Suppliers8 total

上海腾准生物科技有限公司19821570922 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
深圳市简一生物科技有限公司0755-84826604 · [email protected]
艾吉析科技(上海)有限公司17721401538;17717235263 17721401538 · [email protected]

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

5 records

Linked notes

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