HuagongsheHuagongshe Chemistry Print Report · For research reference only
Neomycin Sulfate
Framycin sulfate · neomycin B sulphate · Chlorotoluron Impurity 5 · Neomycin B Sulfate (Framycetin Sulfate) · 2nd International Standard for Neomycin B · Framycetin 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
Identifiers & Physical Properties
| CAS No. | 1405-10-3 |
|---|---|
| Molecular formula | C23H48N6O17S |
| Average molar mass | 712.7 g/mol |
| Monoisotopic mass | 712.27966508 g/mol |
| 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 |
| PubChem CID | 197162 |
| ChEMBL | CHEMBL1950493 |
| ChEBI | CHEBI:53636 |
| EC No. | 215-773-1 |
| DTXSID | DTXSID10948247 |
Chemical & Physical Properties
| Topological polar surface area | 436 |
|---|---|
| Hydrogen bond donors | 15 |
| Hydrogen bond acceptors | 23 |
| Rotatable bonds | 9 |
| Heavy atoms | 47 |
| Formal charge | 0 |
| Complexity | 953 |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsAminoglycosidesDermatologic AgentsFDA approved drugs -> Active ingredient |
| Animal Drugs | Active Ingredients (Neomycin Sulfate) -> FDA Greenbook |
| Storage conditions | -20°C |
| Physical state | solid |
| Major applications | USP Biologicspharmaceutical |
| InChIKey | OIXVKQDWLFHVGR-WQDIDPJDSA-N |
| FDA UNII | Y3720KZ4TQ |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H317 |
| GHS precautionary statements | P261-P272-P280-P302+P352-P333+P313-P362+P364 |
| Water hazard class (WGK) | WGK 3 |
| Storage class | 13 - Non Combustible Solids |
| Hazard class | Skin Sens. 1 |
Safety & Regulations
| GHS classification | DangerH317 (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 |
|---|---|
| Regulatory information | Hazard Traits - Developmental ToxicityNeomycin sulphate: Does not have an individual approval but may be used under an appropriate group standardFramycetin 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 information | IMAP assessments - Neomycin, sulfate (salt): Human health tier I assessment |
| Hazard Classes and Categories | Not ClassifiedSkin Sens. 1 (95.7%)Acute Tox. 4 (15.4%) |
| Treatment | Hemodialysis will remove neomycin sulfate from the blood. (L1712) |
| Health effects | Antibiotic resistance |
| Exposure routes | Eye contacttopical (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. |
| Signs and Symptoms | Vestibular toxicity may result in vertigo, nausea and vomiting, dizziness and loss of balance. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Neomycin sulfatevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Toxicity Data | LD50: 200 mg/kg (Rat) (A308) |
| Water hazard class (WGK) | WGK 3 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Storage class | 13 - Non Combustible Solids |
| GHS hazard statements | H317 |
| Hazard class | Skin Sens. 1 |
| GHS precautionary statements | P261-P272-P280-P302+P352-P333+P313-P362+P364 |
Applications & Uses
Uses
Neomycin B Trisulfate is a trisulfate salt analog of Neomycin B (N389983), which is an aminoglycoside antibiotic.