Amikacin Sulfate Salt

HCID 5458175CAS 149022-22-0

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Basic information

Standard SMILES: NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O.O=S(=O)(O)O
InChIKey: HIBICIOPDUTNRR-XTHCGPPUSA-N
Molecular formula: C22H45N5O17S
Average molar mass: 683.7 g/mol
Monoisotopic mass: 683.25311616

Names & identifiers

Preferred name: Amikacin Sulfate Salt
IUPAC: (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide;sulfuric acid
English name: Amikacin sulfate salt
Molecular formula: C22H45N5O17S
Molecular weight: 683.68

Names & synonyms

Amikacin sulfate saltQB4SJV7YHXRefChem:1076646149022-22-0Amikacin sulfate(5:9)BAY 41-6551 sulfate(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide;sulfuric acidC22H45N5O17SD-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-->6)-O-[6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-->4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-, sulfate (5:9) (salt) (9CI)(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide;sulfuric acidSCHEMBL3340MLS000028568

Show more names

liusuanamukaxonmAMIKASIN SULFATEAmikacinsulfatesalAmikacin Impurity 26AMIKACIN SULFATE 1:1.8mikacin disulfate saltAmikacin Sulfate, USP (1:1.8)Amikacin sulfate salt USP/EP/BP

CHEMBL1164318MFCD00167477NCGC00093350-07SMR000058947(S)-4-Amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide sulfate(5:9)D82929(S)-4-amino-N-((1R,2R,3S,4S,5S)-5-amino-2-(((2S,3R,4S,5S,6S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6S)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide sulfate(S)-4-Amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamidesulfate(5:9)

Database identifiers

CAS: 149022-22-0、39831-55-5
PubChem CID: 5458175
ChEMBL: CHEMBL1164318
UNII: QB4SJV7YHX

Properties

Computed structural properties

Topological polar surface area: 415 Å²
Hydrogen bond donors: 15
Hydrogen bond acceptors: 21
Rotatable bonds: 10
Heavy atoms: 45
Formal charge: 0
Complexity: 900

Physicochemical properties

storage temp.: 2 · Inert atmosphere,2-8°C
solubility: 2 O: · H2O: soluble50mg/mL
form: solid
color: white to off-white
biological source: synthetic
InChIKey: HIBICIOPDUTNRR-BOEHXBESSA-N
SMILES: OS(O)(=O)=O.NCC[C@@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O
UNSPSC Code: 41116107 · 41116107
NACRES: 85 · NA.85
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 317 · H317
Precautionary statements: 261 · P261-P272-P280-P302+P352-P333+P313-P362+P364
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 2 · 2
RTECS: 1961200 · WK1961200
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 · Skin Sens. 1

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
rtecs: WK1961200
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H317
Hazard Classifications: Skin Sens. 1
Precautionary statements: P261-P272-P280-P302+P352-P333+P313-P362+P364

Chemistry & industry

Applications

UsesAmikacin is an aminoglycoside antibiotic commonly used in the treatment of drug-resistant mycobacteria . It is used to study organism-directed delivery of antibiotics as well as drug resistance .

General DescriptionChemical structure: aminoglycoside