(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; bis(sulfuric acid)

• ChemBase ID: 133774
• Molecular Formular: C22H47N5O21S2
• Molecular Mass: 781.75948
• Monoisotopic Mass: 781.22049555
• SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCN)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)N)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CN)O)O)O)N.OS(=O)(=O)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.OS(=O)(=O)O.NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C22H43N5O13.2H2O4S/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;2*1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);2*(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;;/m0../s1
• InChIKey: FXKSEJFHKVNEFI-GCZBSULCSA-N

NAMES AND DATABASE IDS

Names

• 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; bis(sulfuric acid)
• IUPAC Traditional name: amikacin; bis(sulfuric acid)
• Synonyms: Amikacin disulfate salt

Database IDs

• CAS Number: 39831-55-5
• EC Number: 254-648-6
• MDL Number: MFCD00167475
• Beilstein Number: 6172633
• PubChem SID: 24890586; 162228051
• PubChem CID: 38351

CALCULATED PROPERTIES

• Acid pKa: 12.104234
• H Acceptors: 17
• H Donor: 13
• LogD (pH = 5.5): -20.16644
• LogD (pH = 7.4): -15.099279
• Log P: -8.584383
• Molar Refractivity: 129.841 cm^3
• Polarizability: 54.552784 Å^3
• Polar Surface Area: 331.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• RTECS: WK1961200
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Potency: 674-786 μg per mg (as amikacin base)
• Loss on Drying: ≤12% loss on drying
• Empirical Formula (Hill Notation): C22H43N5O13 · 2H2SO4

DETAILS

Sigma Aldrich - A1774

Application
Amikacin is an aminoglycoside antibiotic commonly used in the treatment of drug-resistant mycobacteria 1. It is used to study organism-directed delivery of antibiotics as well as drug resistance 2.
Biochem/physiol Actions
Amikacin prevents bacterial protein synthesis by binding to the 30S ribosome subunit and inducing mRNA misreading.