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.[H][C@]3(O[C@H]1[C@@H](C[C@H](N)[C@@H](O[C@@]2([H])O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O)NC(=O)[C@@H](O)CCN)O[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
145
Curator's Comment: # Bristol-Myers Squibb

Approval Year

1976
91
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 5.27 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Curative
Approved
8429
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
8429
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
8429
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
n = 6
Health Status: healthy
Age Group: 21-30 years
Population Size: 6
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
n = 6
Health Status: healthy
Age Group: 21-30 years
Population Size: 6
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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
n = 15
Health Status: unhealthy
Condition: pulmonary tuberculosis
Age Group: adult
Population Size: 15
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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)
n = 44
Health Status: unhealthy
Age Group: 58.0 years (range: 16 - 61 years)
Sex: M+F
Population Size: 44
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
MolPort
MolPort-000-761-900
https://www.molport.com/shop/molecule-link/MolPort-000-761-900
ZINC
ZINC000008214483
http://zinc15.docking.org/substances/ZINC000008214483
eMolecules
36519241
https://www.emolecules.com/cgi-bin/more?vid=36519241
PubMed

PubMed

TitleDatePubMed
[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)].
1975 Jun
[Multifocal invasive Kingella kingae infection].
1998 Feb
Activities of eighteen antimicrobial regimens against Mycobacterium avium infection in beige mice.
1999 Fall
Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution.
2001
Occurrence of variants with temperature-dependent susceptibility (TDS) to antibiotics among Stenotrophomonas maltophilia clinical strains.
2001
Cutaneous nocardiosis of the chest wall and pleura--10-year consequences of a hand actinomycetoma.
2001
Molecular diagnosis of a Mycobacterium chelonae infection.
2001
Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium.
2001 Apr
The immunomodulatory effects of gentamicin, imipenem, piperacillin and amphotericin B on LAK effector function in vitro.
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
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 Aug
Role of megalin in renal handling of aminoglycosides.
2001 Aug
Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999.
2001 Feb
Efficacy of meropenem as monotherapy in the treatment of ventilator-associated pneumonia.
2001 Feb
Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations.
2001 Feb
Comparative activities of isepamicin, amikacin, cefepime, and ciprofloxacin alone or in combination with other antibiotics against Stenotrophomonas maltophilia.
2001 Jan
[Stab wound of the spinal cord complicated by meningitis and subarachnoid fistula].
2001 Jan
Granulocyte colony-stimulating factor in the treatment of high-risk febrile neutropenia: a multicenter randomized trial.
2001 Jan 3
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
Intravitreal antibiotics: the emergency kit.
2001 Jul
Treatment and outcome of nocardia keratitis.
2001 Jul
Is levofloxacin as active as ciprofloxacin against Pseudomonas aeruginosa?
2001 Jul-Aug
Antibiotic susceptibility and phage typing of methicillin-resistant and -sensitive Staphylococcus aureus clinical isolates at three periods during 1991-1997.
2001 Jun
[Neonatal bacterial infections at the CUH of Dakar].
2001 Jun
Madura foot: treatment of Nocardia nova infection with antibiotics alone.
2001 Jun
Translimbal approach for intravitreal injection in endophthalmitis after phacoemulsification.
2001 Jun
Mycobacterium fortuitum wound infection following laparoscopy.
2001 Mar
Study on antimicrobial susceptibility of bacteria causing neonatal infections: a 12 year study (1987-1998).
2001 Mar
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 Mar
Treatment of nosocomial postoperative pneumonia in cancer patients: a prospective randomized study.
2001 Mar
Systemic antibiotics fail to clear multidrug-resistant Klebsiella from a pediatric ICU.
2001 Mar
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001 May
Effect of Sub-MICs of antibiotics on the hydrophobicity and production of acidic polysaccharide by Vibrio vulnificus.
2001 May-Jun
Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies.
2001 Sep
Failure of treatment for chronic Mycobacterium abscessus meningitis despite adequate clarithromycin levels in cerebrospinal fluid.
2001 Sep 1
Patents

Patents

050618-002
2
062311-001
2
062562-002
2
JP2000219621A
2
JP2002520120A
2
JP2002541233A
400
JP2009541210A
79
JP2011510954A
143
JPS5446840A
2
JPS6293297A
2

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 Fri Dec 15 15:14:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:14:22 GMT 2023
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
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
ARIKAYCE
Brand 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 Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
EU-Orphan Drug EU/3/06/387
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
NCI_THESAURUS C2363
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
AMIKACIN SULFATE
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
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 Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
DRUG BANK
DBSALT000351
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID601045247
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
NCI_THESAURUS
C230
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
PUBCHEM
38351
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
CAS
39831-55-5
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
NSC
755846
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
DAILYMED
N6M33094FD
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL177
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
RS_ITEM_NUM
1019494
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
CHEBI
2638
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
RXCUI
643
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY RxNorm
SMS_ID
100000085153
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
MERCK INDEX
m1670
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY Merck Index
EVMPD
SUB00444MIG
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
FDA UNII
N6M33094FD
Created by admin on Fri Dec 15 15:14:22 GMT 2023 , Edited by admin on Fri Dec 15 15:14:22 GMT 2023
PRIMARY
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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