U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H43N5O13.H2O4S
Molecular Weight 683.681
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Amikacin Sulfate Salt

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

InChI

InChIKey=HIBICIOPDUTNRR-XTHCGPPUSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H43N5O13
Molecular Weight 585.6025
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00479

Amikacin, USP (as the sulfate) is a semi-synthetic aminoglycoside antibiotic derived from kanamycin. Amikacin "irreversibly" binds to specific 30S-subunit proteins and 16S rRNA. Amikacin inhibits protein synthesis by binding to the 30S ribosomal subunit to prevent the formation of an initiation complex with messenger RNA. Specifically Amikacin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes. Amikacin is used for short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin may also be used to treat Mycobacterium avium and Mycobacterium tuberculosis infections. Amikacin was used for the treatment of gram-negative pneumonia.

Originator

Curator's Comment: # Bristol-Myers Squibb

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.27 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Curative
AMIKACIN SULFATE

Approved Use

Amikacin sulfate injection is indicated in the short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin sulfate is effective in bacterial septicemia (including neonatal sepsis).

Launch Date

1993
Curative
AMIKACIN SULFATE

Approved Use

Amikacin sulfate injection is indicated in the short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin sulfate is effective in central nervous system infections (including meningitis)

Launch Date

1993
Curative
AMIKACIN SULFATE

Approved Use

Amikacin sulfate injection is indicated in the short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin sulfate is effective in serious complicated and recurrent urinary tract infections due to these organisms.

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.8 μg/mL
590 mg 1 times / day steady-state, respiratory
dose: 590 mg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
AMIKACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
23.5 μg × h/mL
590 mg 1 times / day steady-state, respiratory
dose: 590 mg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
AMIKACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.9 h
590 mg 1 times / day steady-state, respiratory
dose: 590 mg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
AMIKACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
590 mg 1 times / day steady-state, respiratory
dose: 590 mg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
AMIKACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
15 mg/kg single, intravenous
Highest studied dose
Dose: 15 mg/kg
Route: intravenous
Route: single
Dose: 15 mg/kg
Sources:
healthy, 21-30 years
Health Status: healthy
Age Group: 21-30 years
Sources:
60 mg/kg single, respiratory
Highest studied dose
Dose: 60 mg/kg
Route: respiratory
Route: single
Dose: 60 mg/kg
Sources:
healthy, 21-30 years
Health Status: healthy
Age Group: 21-30 years
Sources:
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Disc. AE: Infective exacerbation of bronchiectasis, Dyspnea...
AEs leading to
discontinuation/dose reduction:
Infective exacerbation of bronchiectasis (6.8%)
Dyspnea (4.5%)
Cough (1 patient)
Oropharyngeal pain (1 patient)
Respiratory disorder (1 patient)
Pneumonia (1 patient)
Sources:
15 mg/kg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 15 mg/kg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 15 mg/kg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, adult
Other AEs: Hypersensitivity pneumonitis, Hemoptysis...
Other AEs:
Hypersensitivity pneumonitis
Hemoptysis
Bronchospasm
Sources:
AEs

AEs

AESignificanceDosePopulation
Cough 1 patient
Disc. AE
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Oropharyngeal pain 1 patient
Disc. AE
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Pneumonia 1 patient
Disc. AE
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Respiratory disorder 1 patient
Disc. AE
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Dyspnea 4.5%
Disc. AE
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Infective exacerbation of bronchiectasis 6.8%
Disc. AE
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
Bronchospasm
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, adult
Hemoptysis
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, adult
Hypersensitivity pneumonitis
590 mg 1 times / day multiple, respiratory
Recommended
Dose: 590 mg, 1 times / day
Route: respiratory
Route: multiple
Dose: 590 mg, 1 times / day
Sources:
unhealthy, adult
PubMed

PubMed

TitleDatePubMed
[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)].
1975 Jun
Amykacin-related apneic episode in an infant on peritoneal dialysis.
2000 Apr
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.
2000 Feb 1
Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution.
2001
Cutaneous nocardiosis of the chest wall and pleura--10-year consequences of a hand actinomycetoma.
2001
[Criteria of low risk of mortality in children with neutropenia and fever during cancer chemotherapy].
2001
The immunomodulatory effects of gentamicin, imipenem, piperacillin and amphotericin B on LAK effector function in vitro.
2001 Apr
Aeromonas sobria sepsis in a neutropenic patient.
2001 Apr
Multiple nocardial abscesses of cerebrum, cerebellum and spinal cord, causing quadriplegia.
2001 Apr
[Combination therapy of antibiotics and intravenous immunoglobulin].
2001 Apr
Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis.
2001 Aug
Comparison of 2 techniques for regional antibiotic delivery to the equine forelimb: intraosseous perfusion vs. intravenous perfusion.
2001 Aug
Role of megalin in renal handling of aminoglycosides.
2001 Aug
Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica.
2001 Aug
[Clinical effects of combination therapy with cefozopran and amikacin for infections in patients with hematological disorders].
2001 Feb
Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999.
2001 Feb
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].
2001 Feb
[Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa].
2001 Feb
Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations.
2001 Feb
Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998).
2001 Feb 1
Objective method for differentiating between drug-induced vestibulotoxicity and cochleotoxicity.
2001 Jan
Carriage of class 1 integrons and antibiotic resistance in clinical isolates of Acinetobacter baumannii from northern Spain.
2001 Jan
Disseminated Mycobacterium abscessus infection manifesting as fever of unknown origin and intra-abdominal lymphadenitis: case report and literature review.
2001 Jan
Bilateral infectious keratitis after laser in situ keratomileusis: a case report and review of the literature.
2001 Jan
Review of 49 neonates with acquired fungal sepsis: further characterization.
2001 Jan
Applications of a copper microparticle-modified carbon fiber microdisk array electrode for the simultaneous determination of aminoglycoside antibiotics by capillary electrophoresis.
2001 Jan 5
Prevalence and characteristics of Pasteurella multocida in commercial turkeys.
2001 Jan-Mar
Changes in electrovestibular brainstem responses after aminoglycoside intoxication in guinea pigs.
2001 Jul
Epidemiology and frequency of resistance among pathogens causing urinary tract infections in 1,510 hospitalized patients: a report from the SENTRY Antimicrobial Surveillance Program (North America).
2001 Jul
Cost-effectiveness of cefepime + netilmicin or ceftazidime + amikacin or meropenem monotherapy in febrile neutropenic children with malignancy in Turkey.
2001 Jun
Antibiotic resistance among Gram-negative non-fermentative bacteria at a teaching hospital in Saudi Arabia.
2001 Jun
Madura foot: treatment of Nocardia nova infection with antibiotics alone.
2001 Jun
Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test.
2001 Jun
Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis.
2001 Jun
Pharmacokinetic longitudinal studies of antibiotics administered via a permanent intraosseous device in micropigs.
2001 Jun
[Clinical analysis of neutropenic fever associated with hematological disorders].
2001 Mar
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.
2001 Mar
[Mycobacterium xenopi: epidemiological and bacteriological features].
2001 Mar-Apr
Ocular nocardia infections with special emphasis on the cornea.
2001 Mar-Apr
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus].
2001 May
Streptococcus agalactiae endocarditis and giant pyomyoma simulating ovarian cancer.
2001 May
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001 May
Antibiotic selective pressure and development of bacterial resistance.
2001 May
Antimicrobial susceptibility of blood culture isolates of viridans streptococci: relationship to a change in empirical antibiotic therapy in febrile neutropenia.
2001 May
In vivo efficacy of continuous infusion versus intermittent dosing of ceftazidime alone or in combination with amikacin relative to human kinetic profiles in a Pseudomonas aeruginosa rabbit endocarditis model.
2001 May
Effect of Sub-MICs of antibiotics on the hydrophobicity and production of acidic polysaccharide by Vibrio vulnificus.
2001 May-Jun
A simple tool for monitoring nebulized amikacin treatments based on a single urine assay.
2001 Spring
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Intravenous Administration The individual dose, the total daily dose, and the total cumulative dose of amikacin sulfate are identical to the dose recommended for intramuscular administration. The solution for intravenous use is prepared by adding the contents of a 500 mg vial to 100 or 200 mL of sterile diluent such as 0.9% sodium chloride injection or 5% dextrose injection or any other compatible solutions listed below. The solution is administered to adults over a 30 to 60 minute period. The total daily dose should not exceed 15 mg/kg/day and may be divided into either 2 or 3 equally-divided doses at equally-divided intervals. Amikacin can also be given by inhalation - The usual dose for adults with CF is 250-500mg twice a day via nebulizer. http://torontoadultcf.com/medications/inhaled-amikacin
The recommended dosage for adults, children and older infants with normal renal function is 15 mg/kg/day divided into 2 or 3 equal doses administered at equally divided intervals, i.e., 7.5 mg/kg q12h or 5 mg/kg q8h. Treatment of patients in the heavier weight classes should not exceed 1.5 grams/day. When amikacin is indicated in newborns, it is recommended that a loading dose of 10 mg/kg be administered initially to be followed with 7.5 mg/kg every 12 hours. The usual duration of treatment is 7 to 10 days. It is desirable to limit the duration of treatment to short-term whenever feasible. The total daily dose by all routes of administration should not exceed 15 mg/kg/day.
Route of Administration: Intramuscular
In Vitro Use Guide
Curator's Comment: Eight P. aeruginosa isolates obtained from clinical samples of burned patients and standard strain ATCC 27853 were used. Amikacin at 4 ug/mL concentration induced lower rate of coccoid bacteria (55.05%). Amikacin had a strong bactericidal effect on coccoid bacteria at 8 ug/mL concentration.
Amikacin had a strong bactericidal effect on coccoid bacteria at 8 ug/mL concentration.
Substance Class Chemical
Created
by admin
on Wed Apr 02 20:56:17 GMT 2025
Edited
by admin
on Wed Apr 02 20:56:17 GMT 2025
Record UNII
QB4SJV7YHX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(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
Preferred Name English
Amikacin Sulfate Salt
Common Name English
D-Streptamine, O-3-amino-3-deoxy-?-D-glucopyranosyl-(1?6)-O-[6-amino-6-deoxy-?-D-glucopyranosyl-(1?4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-, sulfate (5:9) (salt)
Systematic Name English
Code System Code Type Description
PUBCHEM
5458175
Created by admin on Wed Apr 02 20:56:17 GMT 2025 , Edited by admin on Wed Apr 02 20:56:17 GMT 2025
PRIMARY
FDA UNII
QB4SJV7YHX
Created by admin on Wed Apr 02 20:56:17 GMT 2025 , Edited by admin on Wed Apr 02 20:56:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID90933530
Created by admin on Wed Apr 02 20:56:17 GMT 2025 , Edited by admin on Wed Apr 02 20:56:17 GMT 2025
PRIMARY
CAS
149022-22-0
Created by admin on Wed Apr 02 20:56:17 GMT 2025 , Edited by admin on Wed Apr 02 20:56:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE