Accession Number
DB00479  (APRD00550)
Small Molecule
Approved, Investigational, Vet approved

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 [6]. 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].

  • 1-N-(L(−)-γ-amino-α-hydroxybutyryl)kanamycin A
  • Amikacin
  • Amikacina
  • Amikacine
  • Amikacinum
External IDs
BAY 41-6551
Product Ingredients
IngredientUNIICASInChI Key
Amikacin sulfateN6M33094FD39831-55-5FXKSEJFHKVNEFI-GCZBSULCSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amikacin Sulfate Injection USPLiquid250 mgIntramuscular; IntravenousSandoz Canada Incorporated2001-01-29Not applicableCanada
AmikinSolution250 mgIntramuscular; IntravenousBristol Myers Squibb1977-12-312006-05-29Canada
ArikayceSuspension590 mg/8.4mLRespiratory (inhalation)Insmed Incorporated2018-10-12Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amikacin SulfateInjection, solution250 mg/1mLIntramuscular; IntravenousSagent Pharmaceuticals2016-06-15Not applicableUs
Amikacin SulfateInjection, solution250 mg/1mLIntramuscular; IntravenousBedford Pharmaceuticals1997-06-102010-03-31Us
Amikacin SulfateInjection, solution250 mg/1mLIntramuscular; IntravenousFresenius Kabi2015-12-09Not applicableUs
Amikacin SulfateInjection250 mg/1mLIntramuscular; IntravenousWest-Ward Pharmaceuticals Corp.2015-08-01Not applicableUs
Amikacin SulfateInjection, solution250 mg/1mLIntramuscular; IntravenousBedford Pharmaceuticals1994-05-312015-06-30Us
Amikacin SulfateInjection, solution500 mg/2mLIntramuscular; IntravenousTeva Parenteral Medicines, Inc.1993-10-01Not applicableUs
AMIKACIN SulfateInjection, solution500 mg/2mLIntramuscular; IntravenousHospira, Inc.2005-09-122012-11-01Us
Amikacin SulfateInjection, solution250 mg/1mLIntramuscular; IntravenousHeritage2013-12-24Not applicableUs
Amikacin SulfateInjection250 mg/1mLIntramuscular; IntravenousWest-Ward Pharmaceuticals Corp.2015-08-01Not applicableUs
Amikacin SulfateInjection, solution50 mg/1mLIntramuscular; IntravenousFresenius Kabi USA, LLC2015-12-092015-12-14Us
International/Other Brands
Amexel (Abbott) / Amukin (Bristol-Myers Squibb) / Biklin (Bristol-Myers Squibb) / Erkacin (Brown & Burk) / Farcyclin (Faran Laboratories) / Flexelite (Bros) / Kamin (Bosch) / Novamin (Bristol-Myers Squibb) / Selaxa (Proel) / Selemycin (Medochemie) / Sikacin (Shiteh Organic) / Tipkin (T P Drug) / Tybikin (M & H) / Ukaject (Unimed Pharm) / Unikin (Union) / Uzix (Rafarm) / Xylanal (Epsilon)
CAS number
Average: 585.6025
Monoisotopic: 585.285736487
Chemical Formula
InChI Key



The amikacin sulfate injection is indicated in the short-term treatment of serious bacterial 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, as well as Acinetobacter (Mima-Herellea) species [8].

Clinical studies have shown amikacin sulfate injection to be effective in bacterial septicemia (including neonatal sepsis); in serious infections of the respiratory tract, bones and joints, central nervous system (including meningitis) and skin and soft tissue; intra-abdominal infections (including peritonitis); and in burns and postoperative infections (including post-vascular surgery) [8].

Clinical studies have shown amikacin also to be effective in serious, complicated, and recurrent urinary tract infections due to the above organisms. Aminoglycosides, including amikacin, are not indicated in uncomplicated first-time episodes of urinary tract infections unless the causative organisms are not susceptible to antibiotics which are less toxic [8].

In September 2018, a new indication with a new dosage route was approved for this drug. Amikacin liposome inhalation suspension was approved for the treatment of lung disease caused by a group of bacteria, Mycobacterium avium complex (MAC) in a limited population of patients with the disease who do not respond to conventional treatment (refractory disease) [3]. This indication is approved under accelerated approval based on achieving sputum culture conversion (defined as 3 consecutive negative monthly sputum cultures) by Month 6 of treatment. Clinical benefit has not yet been established [Label].

Important notes regarding Staphylococcus and Sensitivity testing:

Staphylococcus aureus, including methicillin-resistant strains, is the principal Gram-positive organism sensitive to amikacin. The use of amikacin in the treatment of staphylococcal infections should be restricted only to second-line therapy, and should be limited to only those patients suffering from severe infections caused by susceptible strains of staphylococcus species who have failed to show sensitivity to other available antibiotics [6].

Bacteriologic studies should be performed to identify causative organisms and their susceptibilities to amikacin. Amikacin may be used as initial therapy in suspected gram-negative infections and therapy may be initiated before obtaining the results of susceptibility testing [Label], [6], [8].

Associated Conditions

Amikacin is an aminoglycoside antibiotic. Aminoglycosides bind to the bacteria, causing misreading of t-RNA, leaving bacteria unable to synthesize proteins vital to their growth. Aminoglycosides are useful mainly in the treatment infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, however, other antibiotics may be more potent and less toxic to humans [Label], [6].

Mechanism of action

The primary mechanism of action of amikacin is the same as that for all aminoglycosides. It binds to bacterial 30S ribosomal subunits and interferes with mRNA binding and tRNA acceptor sites, interfering with bacterial growth. This leads to disruption of normal protein synthesis and production of non-functional or toxic peptides. Other actions have been postulated for drugs of this class [Label], [6], [7]. Amikacin, as well as the rest of the aminoglycosides, are generally bacteriocidal against gram-positive and gram-negative bacteria [4], [8].

A30S ribosomal protein S12
Escherichia coli (strain K12)

Rapidly absorbed after intramuscular administration. Rapid absorption occurs from the peritoneum and pleura. Poor oral and topical absorption. Poorly absorbed from bladder irrigations and intrathecal administration [8], [Label].

The bioavailability of this drug is expected to vary primarily from individual differences in nebulizer efficiency and airway pathology [Label].

Following IM administration of a single dose of amikacin of 7.5 mg/kg in adults with normal renal function, peak plasma amikacin concentrations of 17-25 micrograms/mL are attained within 45 minutes to 2 hours [6].

Following IV infusion of the same dose given over 1 hour peak plasma concentrations of the drug average 38 micrograms/mL immediately following the infusion, 5.5 micrograms/mL at 4 hours, and 1.3 micrograms/mL at 8 hours [6].

Volume of distribution
  • 24 L (28% of body weight healthy adult subjects) [8].

Following administration of usual dosages of amikacin, amikacin has been found in bone, heart, gallbladder, and lung tissue. Amikacin is also distributed into bile, sputum, bronchial secretions, and interstitial, pleural, and synovial fluids [6].

Protein binding

The protein binding of amikacin in serum is ≤ 10% [Label].


Amikacin's structure has been altered to reduce the possible route of enzymatic deactivation, thus reducing bacterial resistance. Many strains of Gram-negative organisms resistant to gentamicin and tobramycin have shown to be sensitive to amikacin in vitro [6].

Route of elimination

This drug is eliminated by the kidneys. In adults with normal renal function, 94-98% of a single IM or IV dose of amikacin is excreted unchanged by glomerular filtration in the kidney within 24 hours. Amikacin can be completely recovered within approximately 10-20 days in patients with normal, healthy renal function [6].

In patients with impaired renal function, the clearance of amikacin is found to be decreased; the more severe the impairment, the slower the clearance. The interval between doses of amikacin should be adjusted according to the level of renal impairment. Endogenous creatinine clearance rate and serum creatinine which have a high correlation with serum half-life of amikacin, may be used as a guide for dosing [6].

Half life

The plasma elimination half-life of amikacin is usually 2-3 hours in adults with normal renal function and is reported to range from 30-86 hours in adults with severe renal impairment [Label].


The mean serum clearance rate is about 100 mL/min and the renal clearance rate is 94 mL/min in subjects with normal renal function [8].


Oral (LD50): 6000 mg/kg (Mouse) [MSDS]. No antidote for toxicity is currently available. This drug is only 20% dialyzable; however, this is variable based on the type hemodialysis filter used [4].


Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in the proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity most commonly occurs several days following initiation of therapy. Amikacin may exacerbate pre-existing renal disease [Label].


May cause irreversible ototoxicity [Label]. Ototoxicity appears to be correlated to cumulative exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High- frequency hearing is lost first with progression leading to loss of low-frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness, and loss of balance [6], [Label].

Neuromuscular blockade

In addition to the above, amikacin may exacerbate neuromuscular blockade, however, this is less common [Label], [4].

Use in Pregnancy

Category D. Gentamicin and other aminoglycosides are known to cross the placenta. There is evidence of selective uptake of gentamicin by the fetal kidney resulting in damage to immature nephrons. Eighth cranial nerve damage has also been reported after in-utero exposure to some of the aminoglycosides. Because of the chemical similarity, all aminoglycosides should be considered potentially nephrotoxic and ototoxic to the developing fetus. Therapeutic blood amikacin levels in the mother do not equate with safety for the fetus. In reproductive toxicity studies in mice and rats, no effects on fertility or fetal toxicity were observed [6].

Use in Lactation

It is not known whether amikacin is excreted in breast milk. Since the possible harmful effect on the infant is not known, it is recommended that if nursing mothers must be given amikacin, the infants should not be breastfed during therapy [6].

Affected organisms
  • Humans and other mammals
  • Enteric bacteria and other eubacteria
Amikacin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
(R)-warfarinThe risk or severity of bleeding can be increased when Amikacin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Amikacin is combined with (S)-Warfarin.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Amikacin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Amikacin is combined with 4-hydroxycoumarin.
AbacavirAmikacin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAmikacin may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Amikacin.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Acemetacin is combined with Amikacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Amikacin is combined with Acenocoumarol.
AcetaminophenAmikacin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
Not Available


Synthesis Reference

Alberto Mangia, Vicenzo Giobbio, Giorgio Ornato, "Novel process for the synthesis of amikacin." U.S. Patent US4902790, issued August, 1984.

General References
  1. Edson RS, Terrell CL: The aminoglycosides. Mayo Clin Proc. 1999 May;74(5):519-28. [PubMed:10319086]
  2. Ramirez MS, Tolmasky ME: Amikacin: Uses, Resistance, and Prospects for Inhibition. Molecules. 2017 Dec 19;22(12). pii: molecules22122267. doi: 10.3390/molecules22122267. [PubMed:29257114]
  3. FDA Approves Arikayce [Link]
  4. Stat Pearls: Amikacin [Link]
  5. FDA approves a new antibacterial drug to treat a serious lung disease using a novel pathway to spur innovation [Link]
  6. MedSafe NZ: Amikacin Injection [File]
  7. EMA Withdrawal document, Arikayce [File]
  8. Amikacin, DailyMed [File]
External Links
Human Metabolome Database
KEGG Compound
PubChem Compound
PubChem Substance
Therapeutic Targets Database
RxList Drug Page Drug Page
ATC Codes
J01RA06 — Cefepime and amikacinS01AA21 — AmikacinD06AX12 — AmikacinJ01GB06 — Amikacin
AHFS Codes
  • 08:12.02 — Aminoglycosides
PDB Entries
4p20 / 6cgd
FDA label
Download (3.36 MB)
Download (73.4 KB)

Clinical Trials

Clinical Trials
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers1
1, 2CompletedTreatmentCystic Fibrosis (CF)1
2Active Not RecruitingTreatmentMycobacteria, Atypical / Mycobacterium Infections, Nontuberculous1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
2CompletedTreatmentMycobacterium Infections, Nontuberculous1
2WithdrawnTreatmentPulmonary Non-tuberculous Mycobacterial Lung Disease1
2, 3Unknown StatusTreatmentVentilator-associated Bacterial Pneumonia1
3Active Not RecruitingTreatmentMycobacterium Infections, Nontuberculous1
3CompletedTreatmentCystic Fibrosis (CF)1
3CompletedTreatmentNosocomial Neonatal Sepsis1
3CompletedTreatmentPseudomonas Aeruginosa Infection1
4Active Not RecruitingTreatmentInfection NOS1
4Active Not RecruitingTreatmentNon-Cystic Fibrosis Bronchiectasis1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedPreventionNeonatal Sepsis1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableCompletedTreatmentFevers / Malignancies / Neutropenias1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableCompletedTreatmentPneumonia1
Not AvailableCompletedTreatmentVentilator-Associated Pneumonia (VAP)1
Not AvailableCompletedTreatmentVentilator-associated Bacterial Pneumonia1
Not AvailableRecruitingNot AvailableTuberculosis Infection1
Not AvailableRecruitingDiagnosticCystic Fibrosis (CF)1
Not AvailableRecruitingTreatmentAppendicitis / General Surgery1


  • Abbott laboratories
  • Abbott laboratories hosp products div
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Teva parenteral medicines inc
  • Apothecon inc div bristol myers squibb
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bristol-Myers Squibb Co.
  • Hospira Inc.
  • Mead Johnson and Co.
  • Medisca Inc.
  • Sicor Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
InjectionIntramuscular; Intravenous250 mg/1mL
Injection, solutionIntramuscular; Intravenous1 g/4mL
Injection, solutionIntramuscular; Intravenous100 mg/2mL
Injection, solutionIntramuscular; Intravenous500 mg/2mL
LiquidIntramuscular; Intravenous250 mg
Injection, solutionIntramuscular; Intravenous250 mg/1mL
Injection, solutionIntramuscular; Intravenous50 mg/1mL
SolutionIntramuscular; Intravenous250 mg
SuspensionRespiratory (inhalation)590 mg/8.4mL
Unit descriptionCostUnit
Amikacin sulfate powder26.01USD g
Amikacin (pf) 500 mg/2 ml2.53USD ml
Amikacin 250 mg/ml vial2.19USD ml
Amikacin (pf) 100 mg/2 ml1.8USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Not Available


Experimental Properties
melting point (°C)214MSDS
boiling point (°C)632.23
water solubility50 mg/ml
logS-0.5ADME Research, USCD:
Predicted Properties
Water Solubility49.7 mg/mLALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area331.94 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity129.84 m3·mol-1ChemAxon
Polarizability58.06 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Human Intestinal Absorption-0.9405
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7583
P-glycoprotein substrateSubstrate0.5129
P-glycoprotein inhibitor INon-inhibitor0.7336
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8614
CYP450 2C9 substrateNon-substrate0.816
CYP450 2D6 substrateNon-substrate0.8309
CYP450 3A4 substrateNon-substrate0.5664
CYP450 1A2 substrateNon-inhibitor0.9381
CYP450 2C9 inhibitorNon-inhibitor0.9237
CYP450 2D6 inhibitorNon-inhibitor0.9249
CYP450 2C19 inhibitorNon-inhibitor0.9128
CYP450 3A4 inhibitorNon-inhibitor0.9434
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8866
Ames testNon AMES toxic0.6813
BiodegradationNot ready biodegradable0.5512
Rat acute toxicity1.7506 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9926
hERG inhibition (predictor II)Non-inhibitor0.6366
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available


This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
Organic compounds
Super Class
Organic oxygen compounds
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
4,6-disubstituted 2-deoxystreptamines
Alternative Parents
Gamma amino acids and derivatives / O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexanols / Cyclohexylamines / Oxanes / Monosaccharides / N-acyl amines / 1,3-aminoalcohols / 1,2-aminoalcohols
show 10 more
4,6-disubstituted 2-deoxystreptamine / Gamma amino acid or derivatives / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Fatty acyl / Monosaccharide / N-acyl-amine
show 27 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
alpha-D-glucoside, aminoglycoside, carboxamide, amino cyclitol glycoside (CHEBI:2637)


Escherichia coli (strain K12)
Pharmacological action
General Function
Trna binding
Specific Function
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
Gene Name
Uniprot ID
Uniprot Name
30S ribosomal protein S12
Molecular Weight
13736.995 Da
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Tolmasky ME: Bacterial resistance to aminoglycosides and beta-lactams: the Tn1331 transposon paradigm. Front Biosci. 2000 Jan 1;5:D20-9. [PubMed:10702385]
  4. Amikacin, DailyMed [File]
  5. MedSafe NZ: Amikacin Injection [File]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 10:56