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
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
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 |
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 |
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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 |
---|---|---|
[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)]. | 1975 Jun |
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Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution. | 2001 |
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Cutaneous nocardiosis of the chest wall and pleura--10-year consequences of a hand actinomycetoma. | 2001 |
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Molecular diagnosis of a Mycobacterium chelonae infection. | 2001 |
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Pharmacokinetics of amikacin after single intravenous and intramuscular administration in calves. | 2001 Apr |
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The immunomodulatory effects of gentamicin, imipenem, piperacillin and amphotericin B on LAK effector function in vitro. | 2001 Apr |
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Aeromonas sobria sepsis in a neutropenic patient. | 2001 Apr |
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[Combination therapy of antibiotics and intravenous immunoglobulin]. | 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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Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis. | 2001 Aug |
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Role of megalin in renal handling of aminoglycosides. | 2001 Aug |
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Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica. | 2001 Aug |
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[Clinical effects of combination therapy with cefozopran and amikacin for infections in patients with hematological disorders]. | 2001 Feb |
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Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999. | 2001 Feb |
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[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
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[Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa]. | 2001 Feb |
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Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998). | 2001 Feb 1 |
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Disseminated Mycobacterium abscessus infection manifesting as fever of unknown origin and intra-abdominal lymphadenitis: case report and literature review. | 2001 Jan |
|
Bilateral infectious keratitis after laser in situ keratomileusis: a case report and review of the literature. | 2001 Jan |
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Review of 49 neonates with acquired fungal sepsis: further characterization. | 2001 Jan |
|
Granulocyte colony-stimulating factor in the treatment of high-risk febrile neutropenia: a multicenter randomized trial. | 2001 Jan 3 |
|
Acinetobacter infections in patients with human immunodeficiency virus infection: microbiological and clinical epidemiology. | 2001 Jan-Feb |
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Changes in electrovestibular brainstem responses after aminoglycoside intoxication in guinea pigs. | 2001 Jul |
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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 |
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Intravitreal antibiotics: the emergency kit. | 2001 Jul |
|
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 Jul-Aug |
|
Blood stream infections in a medical intensive care unit: spectrum and antibiotic susceptibility pattern. | 2001 Jun |
|
Antibiotic resistance among Gram-negative non-fermentative bacteria at a teaching hospital in Saudi Arabia. | 2001 Jun |
|
Changing antibiotic sensitivity patterns at a university hospital, 1992 through 1999. | 2001 Jun |
|
Madura foot: treatment of Nocardia nova infection with antibiotics alone. | 2001 Jun |
|
Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test. | 2001 Jun |
|
Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis. | 2001 Jun |
|
Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux. | 2001 Jun |
|
Pharmacokinetic longitudinal studies of antibiotics administered via a permanent intraosseous device in micropigs. | 2001 Jun |
|
Mycobacterium fortuitum wound infection following laparoscopy. | 2001 Mar |
|
Meningoencephalitis caused by Bacillus cereus in a neonate. | 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 |
|
[Mycobacterium xenopi: epidemiological and bacteriological features]. | 2001 Mar-Apr |
|
Ocular nocardia infections with special emphasis on the cornea. | 2001 Mar-Apr |
|
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus]. | 2001 May |
|
Streptococcus agalactiae endocarditis and giant pyomyoma simulating ovarian cancer. | 2001 May |
|
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico. | 2001 May |
|
Antibiotic selective pressure and development of bacterial resistance. | 2001 May |
|
In vivo efficacy of continuous infusion versus intermittent dosing of ceftazidime alone or in combination with amikacin relative to human kinetic profiles in a Pseudomonas aeruginosa rabbit endocarditis model. | 2001 May |
|
Bacterial isolates from blood and their susceptibility patterns in critically ill foals: 543 cases (1991-1998). | 2001 May 15 |
|
Infective endocarditis due to an unusual serotype of Salmonella. | 2001 May-Jun |
|
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology. | 2001 May-Jun |
|
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs. | 2001 May-Jun |
|
Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies. | 2001 Sep |
|
Trends in antimicrobial resistance of Salmonella isolated from animals, foods of animal origin, and the environment of animal production in Canada, 1994-1997. | 2001 Summer |
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
by
admin
on
Edited
Mon Mar 31 17:51:18 GMT 2025
by
admin
on
Mon Mar 31 17:51:18 GMT 2025
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Record UNII |
N6M33094FD
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
458114
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EU-Orphan Drug |
EU/3/06/387
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NCI_THESAURUS |
C2363
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Code System | Code | Type | Description | ||
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AMIKACIN SULFATE
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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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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. | ||
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254-648-6
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DBSALT000351
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DTXSID601045247
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C230
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38351
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39831-55-5
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755846
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N6M33094FD
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CHEMBL177
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1019494
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2638
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643
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100000085153
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m1670
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SUB00444MIG
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
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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.
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IMPURITY -> PARENT |
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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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