Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H43N5O13 |
Molecular Weight | 585.6025 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 16 / 16 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=LKCWBDHBTVXHDL-RMDFUYIESA-N
InChI=1S/C22H43N5O13/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/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
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 |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6ec3129b-c53b-4bdb-913d-a2d0060fa140Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00479
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6ec3129b-c53b-4bdb-913d-a2d0060fa140
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
Sources: http://www.tmfile.com/mark/?q=731096386
Curator's Comment: # Bristol-Myers Squibb
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1641336 Sources: http://www.drugbank.ca/drugs/DB00479 |
5.27 mM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://www.ncbi.nlm.nih.gov/pubmed/868912 |
Curative | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Curative | AMIKACIN SULFATE Approved UseAmikacin 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 Date1993 |
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Curative | AMIKACIN SULFATE Approved UseAmikacin 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 Date1993 |
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Curative | AMIKACIN SULFATE Approved UseAmikacin 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 Date1993 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 |
|
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 |
|
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%) Sources: Dyspnea (4.5%) Cough (1 patient) Oropharyngeal pain (1 patient) Respiratory disorder (1 patient) Pneumonia (1 patient) |
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 |
|
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 Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Hypersensitivity pneumonitis, Hemoptysis... Other AEs: Hypersensitivity pneumonitis Sources: Hemoptysis Bronchospasm |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 Health Status: unhealthy Age Group: adult Sources: |
|
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 Health Status: unhealthy Age Group: adult Sources: |
|
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 Health Status: unhealthy Age Group: adult Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Multiple nocardial abscesses of cerebrum, cerebellum and spinal cord, causing quadriplegia. | 2001 Apr |
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Monotherapy with meropenem versus combination therapy with piperacillin plus amikacin as empiric therapy for neutropenic fever in children with lymphoma and solid tumors. | 2001 Apr-Jun |
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Role of megalin in renal handling of aminoglycosides. | 2001 Aug |
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Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998). | 2001 Feb 1 |
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Objective method for differentiating between drug-induced vestibulotoxicity and cochleotoxicity. | 2001 Jan |
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Carriage of class 1 integrons and antibiotic resistance in clinical isolates of Acinetobacter baumannii from northern Spain. | 2001 Jan |
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Nosocomial pneumonia. Diagnostic and therapeutic considerations. | 2001 Jan |
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Granulocyte colony-stimulating factor in the treatment of high-risk febrile neutropenia: a multicenter randomized trial. | 2001 Jan 3 |
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Applications of a copper microparticle-modified carbon fiber microdisk array electrode for the simultaneous determination of aminoglycoside antibiotics by capillary electrophoresis. | 2001 Jan 5 |
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Treatment and outcome of nocardia keratitis. | 2001 Jul |
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Antibiotic susceptibility and phage typing of methicillin-resistant and -sensitive Staphylococcus aureus clinical isolates at three periods during 1991-1997. | 2001 Jun |
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Cost-effectiveness of cefepime + netilmicin or ceftazidime + amikacin or meropenem monotherapy in febrile neutropenic children with malignancy in Turkey. | 2001 Jun |
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Antibiotic resistance among Gram-negative non-fermentative bacteria at a teaching hospital in Saudi Arabia. | 2001 Jun |
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Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test. | 2001 Jun |
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Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis. | 2001 Jun |
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Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux. | 2001 Jun |
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Pharmacokinetic longitudinal studies of antibiotics administered via a permanent intraosseous device in micropigs. | 2001 Jun |
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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 |
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Streptococcus agalactiae endocarditis and giant pyomyoma simulating ovarian cancer. | 2001 May |
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Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies. | 2001 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6ec3129b-c53b-4bdb-913d-a2d0060fa140
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/26855743
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
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on
Edited
Mon Mar 31 17:46:49 GMT 2025
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Mon Mar 31 17:46:49 GMT 2025
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Record UNII |
84319SGC3C
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175477
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CFR |
21 CFR 522.56
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WHO-ATC |
D06AX12
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FDA ORPHAN DRUG |
342011
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WHO-VATC |
QJ01GB06
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LIVERTOX |
NBK548695
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NDF-RT |
N0000007853
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FDA ORPHAN DRUG |
217305
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WHO-VATC |
QD06AX12
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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FDA ORPHAN DRUG |
507715
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CFR |
21 CFR 862.3035
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WHO-ATC |
J01GB06
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FDA ORPHAN DRUG |
282109
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WHO-ATC |
S01AA21
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WHO-ATC |
J01RA06
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NCI_THESAURUS |
C2363
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WHO-VATC |
QS01AA21
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Code System | Code | Type | Description | ||
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AMIKACIN
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PRIMARY | Description: White or almost white powder. Solubility: Freely soluble in water, practically insoluble in acetone R or ethanol (~750 g/l) TS. Category: Antibacterial. Storage: Amikacin should be kept in a tightly closed container, or if sterile, in a hermetically closed container. Labelling: The label states:- where applicable, that the substances is free from bacterial endotoxins,- where applicable, that the substance is sterile. Definition: Amikacin is a semi-synthetic product derived from a fermentation product, kanamycin A. Amikacin contains not less than 96.5% and not more than 102.0% (Assay, Method A) or not less than 98.5% and not more than 101.0% (Assay, Method B) of amikacin (C22H43N5O13), calculated with reference to the anhydrous substance. | ||
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C61615
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157
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AMIKACIN
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PRIMARY | |||
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CHEMBL177
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37517-28-5
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1019508
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100000092483
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D000583
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3583
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DTXSID3022586
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253-538-5
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84319SGC3C
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177001
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37768
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Amikacin
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SUB05431MIG
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3492
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641
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2637
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DB00479
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m1670
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84319SGC3C
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
Amikacin is a semi-synthetic product derived from a fermentation product, kanamycin A. Amikacin contains not less than 96.5% and not more than 102.0% (Assay, Method A) or not less than 98.5% and not more than 101.0% (Assay, Method B) of amikacin (C22H43N5O13), calculated with reference to the anhydrous substance.
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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