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Amikacin (sulfate)

CAT: 0804-HY-107813-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-107813-01Size:50 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Amikacin sulfate (BAY 41-6551 sulfate) is an aminoglycoside antibiotic and a semisynthetic analog of kanamycin. Amikacin sulfate is bactericidal, acting directly on the 30S and 50S bacerial ribosomal subunits to inhibit protein synthesis. Amikacin sulfate is very active against most Gram-negative bacteria including gentamicin- and tobramycin-resistant strains. Amikacin sulfate also inhibits the infections caused by susceptible Nocardia and nontuberculous mycobacteria[1][2].
CAS Number
149022-22-0
Product Name Alternative
BAY 41-6551 (sulfate)
UNSPSC
12352211
Hazard Statement
H317
Target
Antibiotic; Bacterial
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/amikacin-sulfate-1.html
Purity
99.91
Solubility
H2O : 25 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O[C@@H]1[C@H]([C@@H](C[C@H](N)[C@H]1O[C@@]([C@@H]([C@@H](O)[C@@H]2O)O)([H])O[C@@H]2CN)NC([C@@H](O)CCN)=O)O[C@@]([C@@H]([C@@H](N)[C@@H]3O)O)([H])O[C@@H]3CO.O=[S](O)(O)=O.[9/5]
Molecular Formula
C22H43N5O13.9/5H2O4S
Molecular Weight
762.14
Precautions
H317
References & Citations
[1]Edson, R.S. and C.L. Terrell, The aminoglycosides. Mayo Clin Proc, 1999. 74 (5) : p. 519-28.|[2]Ristuccia AM, et al. An overview of amikacin. Ther Drug Monit. 1985;7 (1) :12-25.|[3]Siân R Kitcher, et al. ORC-13661 Protects Sensory Hair Cells From Aminoglycoside and Cisplatin Ototoxicity. JCI Insight. 2019 Aug 8;4 (15) :e126764.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Aminoglycoside

Chemical Information

Amikacin Sulfate Salt

See also: Amikacin sulfate 1:1.8 (annotation moved to).

CAS Number149022-22-0
PubChem CID5458175
IUPAC Name(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
Molecular FormulaC22H45N5O17S
Molecular Weight683.7
Topological Polar Surface Area415
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count21
Rotatable Bond Count10
Heavy Atom Count45
Formal Charge0
Complexity900
SMILES
C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCN)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N.OS(=O)(=O)O
InChI
InChI=1S/C22H43N5O13.H2O4S/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21;1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;/m0./s1
InChIKey
HIBICIOPDUTNRR-XTHCGPPUSA-N
Chemical Structure
2D Structure
2D structure of Amikacin Sulfate Salt
CAS: 149022-22-0
CID: 5458175
Formula: C22H45N5O17S
MW: 683.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight683.7
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count21
Rotatable Bond Count10
Exact Mass683.25311616
Monoisotopic Mass683.25311616
Topological Polar Surface Area415 Ų
Heavy Atom Count45
Formal Charge0
Complexity900
Isotope Atom Count0
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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