U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H43N5O13.2H2O4S
Molecular Weight 781.759
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIKACIN SULFATE

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]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O

InChI

InChIKey=FXKSEJFHKVNEFI-GCZBSULCSA-N
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

HIDE SMILES / InChI
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
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

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.

CNS Activity

Originator

Bristol-Myers Squibb
144
Curator's Comment: # Bristol-Myers Squibb

Approval Year

1976
92
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 5.27 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase III
665
Unknown

Approved Use

Unknown
Curative
Approved
8583
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
Approved
8583
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
Approved
8583
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/18046534
healthy, 21-30 years
Health Status: healthy
Age Group: 21-30 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/18046534
Sources:
https://pubmed.ncbi.nlm.nih.gov/18046534
60 mg/kg single, respiratory
Highest studied dose
Dose: 60 mg/kg
Route: respiratory
Route: single
Dose: 60 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/18046534
healthy, 21-30 years
Health Status: healthy
Age Group: 21-30 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/18046534
Sources:
https://pubmed.ncbi.nlm.nih.gov/18046534
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/11409580
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/11409580
Sources:
https://pubmed.ncbi.nlm.nih.gov/11409580
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
Other AEs: Hypersensitivity pneumonitis, Hemoptysis...
Other AEs:
Hypersensitivity pneumonitis
Hemoptysis
Bronchospasm
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://pubmed.ncbi.nlm.nih.gov/27748623
unhealthy, 58.0 years (range: 16 - 61 years)
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27748623
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/207356s000lbl.pdf
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:2637
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2637
ChemicalBook
CB8146049
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8146049
eMolecules
36519241
https://www.emolecules.com/cgi-bin/more?vid=36519241
MolPort
MolPort-000-761-900
https://www.molport.com/shop/molecule-link/MolPort-000-761-900
ZINC
ZINC000008214483
http://zinc15.docking.org/substances/ZINC000008214483
PubMed

PubMed

TitleDatePubMed
Failure of treatment for chronic Mycobacterium abscessus meningitis despite adequate clarithromycin levels in cerebrospinal fluid.
2001-09-01
Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies.
2001-09
Infective endocarditis due to an unusual serotype of Salmonella.
2001-08-23
Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis.
2001-08
Comparison of 2 techniques for regional antibiotic delivery to the equine forelimb: intraosseous perfusion vs. intravenous perfusion.
2001-08
Optimizing antibiotic therapy in the intensive care unit setting.
2001-08
Once-a-day individualized amikacin dosing for suspected infection at birth based on population pharmacokinetic models.
2001-08
Serum pharmacokinetics and sputum penetration of amikacin 30 mg/kg once daily and of ceftazidime 200 mg/kg/day as a continuous infusion in cystic fibrosis patients.
2001-08
Role of megalin in renal handling of aminoglycosides.
2001-08
Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica.
2001-08
Monotherapy with meropenem versus combination therapy with piperacillin plus amikacin as empiric therapy for neutropenic fever in children with lymphoma and solid tumors.
2001-07-04
Changes in electrovestibular brainstem responses after aminoglycoside intoxication in guinea pigs.
2001-07
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).
2001-07
Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii.
2001-07
Intravitreal antibiotics: the emergency kit.
2001-07
Treatment and outcome of nocardia keratitis.
2001-07
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.
2001-06-23
Penetration of amikacin into aqueous humor of rabbits.
2001-06-16
In vitro effect of amikacin, imipenem, cefodizime, IFNalpha-2a alone and combinations of antibiotics with IFNalpha-2a on polymorphonuclear leukocyte function in chronic hepatitis patients.
2001-06-16
Is levofloxacin as active as ciprofloxacin against Pseudomonas aeruginosa?
2001-06-16
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs.
2001-06-08
In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals.
2001-06
Antibiotic susceptibility and phage typing of methicillin-resistant and -sensitive Staphylococcus aureus clinical isolates at three periods during 1991-1997.
2001-06
Blood stream infections in a medical intensive care unit: spectrum and antibiotic susceptibility pattern.
2001-06
[Neonatal bacterial infections at the CUH of Dakar].
2001-06
Cost-effectiveness of cefepime + netilmicin or ceftazidime + amikacin or meropenem monotherapy in febrile neutropenic children with malignancy in Turkey.
2001-06
Antibiotic resistance among Gram-negative non-fermentative bacteria at a teaching hospital in Saudi Arabia.
2001-06
Changing antibiotic sensitivity patterns at a university hospital, 1992 through 1999.
2001-06
Madura foot: treatment of Nocardia nova infection with antibiotics alone.
2001-06
The early bactericidal activity of amikacin in pulmonary tuberculosis.
2001-06
Translimbal approach for intravitreal injection in endophthalmitis after phacoemulsification.
2001-06
Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test.
2001-06
Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis.
2001-06
Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux.
2001-06
Pharmacokinetic longitudinal studies of antibiotics administered via a permanent intraosseous device in micropigs.
2001-06
Bacterial isolates from blood and their susceptibility patterns in critically ill foals: 543 cases (1991-1998).
2001-05-15
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus].
2001-05
Streptococcus agalactiae endocarditis and giant pyomyoma simulating ovarian cancer.
2001-05
Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium.
2001-04
Pharmacokinetics of amikacin after single intravenous and intramuscular administration in calves.
2001-04
Mycobacterium fortuitum wound infection following laparoscopy.
2001-03
Meningoencephalitis caused by Bacillus cereus in a neonate.
2001-03
Study on antimicrobial susceptibility of bacteria causing neonatal infections: a 12 year study (1987-1998).
2001-03
Efficacy and tolerability of piperacillin/tazobactam versus ceftazidime in association with amikacin for treating nosocomial pneumonia in intensive care patients: a prospective randomized multicenter trial.
2001-03
Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution.
2001
Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis.
2001
Occurrence of variants with temperature-dependent susceptibility (TDS) to antibiotics among Stenotrophomonas maltophilia clinical strains.
2001
A simple tool for monitoring nebulized amikacin treatments based on a single urine assay.
2001
Trends in antimicrobial resistance of Salmonella isolated from animals, foods of animal origin, and the environment of animal production in Canada, 1994-1997.
2001
[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)].
1975-06
Patents

Patents

050618-002
3
062311-001
3
062562-002
3
JP2000219621A
3
JP2002520120A
3
JP2002541233A
406
JP2009541210A
80
JP2011510954A
147
JPS5446840A
3
JPS6293297A
3

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 Mon Mar 31 17:51:18 GMT 2025
Edited
by admin
on Mon Mar 31 17:51:18 GMT 2025
Record UNII
N6M33094FD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMIKACIN SULFATE
EP   GREEN BOOK   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official Name English
ARIKAYCE
Preferred Name English
AMIKACIN SULFATE [USP-RS]
Common Name English
AMIKACIN SULFATE [GREEN BOOK]
Common Name English
BB-K8
Code English
AMIKACINI SULFAS [WHO-IP]
Common Name English
AMIKACIN SULFATE [MI]
Common Name English
AMIKACIN SULFATE [USAN]
Common Name English
D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-N(SUP 1)-(4-AMINO-2-HYDROXY-1-OXOBUTYL)-2-DEOXY-, (S)-, SULPHATE (1:2) (SALT)
Common Name English
AMIKACIN SULFATE [JAN]
Common Name English
O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6))-N(SUP 3)-(4-AMINO-L-2-HYDROXYBUTYRYL)-2-DEOXY-L-STREPTAMINE SULPHATE (1:2)
Common Name English
AMIKIN
Brand Name English
Amikacin sulfate [WHO-DD]
Common Name English
AMIKACIN SULPHATE
Common Name English
AMIKACIN SULFATE [EP IMPURITY]
Common Name English
D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-N(SUP 1)-(4-AMINO-2-HYDROXY-1-OXOBUTYL)-2-DEOXY-, (S)-, SULFATE (1:2) (SALT)
Common Name English
AMIKACIN SULFATE [MART.]
Common Name English
AMIKACIN SULFATE [USP MONOGRAPH]
Common Name English
AMIKACIN SULFATE [EP MONOGRAPH]
Common Name English
AMIKACIN (AS SULFATE)
Common Name English
AMIKACIN SULFATE [VANDF]
Common Name English
O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6))-N(SUP 3)-(4-AMINO-L-2-HYDROXYBUTYRYL)-2-DEOXY-L-STREPTAMINE SULFATE (1:2)
Common Name English
AMIKACIN SULFATE [ORANGE BOOK]
Common Name English
NSC-755846
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 458114
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
EU-Orphan Drug EU/3/06/387
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
NCI_THESAURUS C2363
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
AMIKACIN SULFATE
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY Description: White or almost white, crystalline powder. Solubility: Freely soluble in water, practically insoluble in acetone R or ethanol (~750 g/l) TS. Category: Antibacterial. Storage: Amikacin sulfate should be kept in a tightly closed container, or if sterile, in a hermetically closed container. Labelling: The label states:- whether the substance is the (1:2) sulfate or the (1:1.8) sulfate form,- the content in terms of Amikacin, calculated with reference to the dried and sulfate-free substance,- where applicable, that the substances is free from bacterial endotoxins,- where applicable, that the substance is sterile.
ECHA (EC/EINECS)
254-648-6
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY
DRUG BANK
DBSALT000351
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID601045247
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY
NCI_THESAURUS
C230
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY
PUBCHEM
38351
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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CAS
39831-55-5
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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NSC
755846
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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DAILYMED
N6M33094FD
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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ChEMBL
CHEMBL177
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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RS_ITEM_NUM
1019494
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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CHEBI
2638
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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RXCUI
643
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY RxNorm
SMS_ID
100000085153
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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MERCK INDEX
m1670
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
PRIMARY Merck Index
EVMPD
SUB00444MIG
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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FDA UNII
N6M33094FD
Created by admin on Mon Mar 31 17:51:18 GMT 2025 , Edited by admin on Mon Mar 31 17:51:18 GMT 2025
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Related Record Type Details
Structure of AMIKACIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of 4-AMINO-2-HYDROXYBUTYRIC ACID, (S)-(-)-
IMPURITY -> PARENT
Structure of KANAMYCIN A
IMPURITY -> PARENT
Amikacin sulfate is a semi-synthetic product derived from a fermentation product, kanamycin A. Amikacin sulfate (1:2) contains not less than 96.5% and not more than 102.0% of amikacin sulfate (C22H43N5O13,2H2SO4), calculated with reference to the dried substance. Amikacin sulfate (1:1.8) contains not less than 96.5% and not more than 102.0% of amikacin sulfate (C22H43N5O13,1.8H2SO4), calculated with reference to the dried substance.
KANAMYCIN
IMPURITY -> PARENT
Related Record Type Details
Structure of AMIKACIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
NIH
NCATS
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