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

See full entry for Amikacin

Accession Number

DBSALT000351

Structure

Similar Structures

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

Amikacin sulfateProduct ingredient for Amikacin

Structure for Amikacin sulfate (DBSALT000351)