Amikacin sulfateProduct ingredient for Amikacin
- Name
- Amikacin sulfate
- Drug Entry
- Amikacin
Amikacin is a semi-synthetic aminoglycoside antibiotic that is derived from kanamycin A.Label Amikacin is synthesized by acylation with the l-(-)-γ-amino-α-hydroxybutyryl side chain at the C-1 amino group of the deoxystreptamine moiety of kanamycin A.2
Amikacin's unique property is that it exerts activity against more resistant gram-negative bacilli such as Acinetobacter baumanii and Pseudomonas aeruginosa. Amikacin also exerts excellent activity against most aerobic gram-negative bacilli from the Enterobacteriaceae family, including Nocardia and some Mycobacterium (M. avium-intracellulare, M. chelonae, and M. fortuitum)4. M. avium-intracellulare (MAC) is a type of nontuberculous mycobacteria (NTM) found in water and soil. Symptoms of this disease include a persistent cough, fatigue, weight loss, night sweats, and shortness of breath and the coughing up of blood.4
Several forms of amikacin are used currently, including an intravenous (IV) or intramuscular (IM) injection.7 In September 2018, a liposomal inhalation suspension of this drug was approved by the FDA for the treatment of lung disease caused by Mycobacterium avium complex (MAC) bacteria in a small population of patients with the disease who do not respond to traditional treatment.4,5
- Accession Number
- DBSALT000351
- Structure
- Synonyms
- Amikacin sulphate
- External IDs
- BB-K8
- UNII
- N6M33094FD
- CAS Number
- 39831-55-5
- Weight
- Average: 781.759
Monoisotopic: 781.220494971 - Chemical Formula
- C22H47N5O21S2
- InChI Key
- FXKSEJFHKVNEFI-GCZBSULCSA-N
- 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
- 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)
- SMILES
- OS(O)(=O)=O.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]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
- External Links
- PubChem Compound
- 38351
- ChemSpider
- 35151
- ChEBI
- 2638
- ChEMBL
- CHEMBL4208954
- Wikipedia
- Amikacin
- Predicted Properties
Property Value Source Water Solubility 49.7 mg/mL ALOGPS logP -3.2 ALOGPS logP -8.6 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 12.1 Chemaxon pKa (Strongest Basic) 9.79 Chemaxon Physiological Charge 4 Chemaxon Hydrogen Acceptor Count 17 Chemaxon Hydrogen Donor Count 13 Chemaxon Polar Surface Area 331.94 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 129.84 m3·mol-1 Chemaxon Polarizability 57.73 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon