Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H43N5O13 |
Molecular Weight | 585.6034 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 16 / 16 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CN)[C@@]([H])(C(=N[C@]1([H])C[C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])O[C@]2([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O2)O)N)O)O)O[C@]3([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CN)O3)O)O)O)N)O)O
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
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 Date7.4917439E11 |
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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 Date7.4917439E11 |
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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 Date7.4917439E11 |
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 n = 6 Health Status: healthy Age Group: 21-30 years Population Size: 6 Sources: |
|
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 n = 6 Health Status: healthy Age Group: 21-30 years Population Size: 6 Sources: |
|
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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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 n = 15 Health Status: unhealthy Condition: pulmonary tuberculosis Age Group: adult Population Size: 15 Sources: |
|
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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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) n = 44 Health Status: unhealthy Age Group: 58.0 years (range: 16 - 61 years) Sex: M+F Population Size: 44 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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Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis. | 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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Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium. | 2001 Apr |
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Multiple nocardial abscesses of cerebrum, cerebellum and spinal cord, causing quadriplegia. | 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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Comparison of 2 techniques for regional antibiotic delivery to the equine forelimb: intraosseous perfusion vs. intravenous perfusion. | 2001 Aug |
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Optimizing antibiotic therapy in the intensive care unit setting. | 2001 Aug |
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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 |
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Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999. | 2001 Feb |
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Antibacterial activity of 41 antimicrobials tested against over 2773 bacterial isolates from hospitalized patients with pneumonia: I--results from the SENTRY Antimicrobial Surveillance Program (North America, 1998). | 2001 Feb |
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Novel treatment of meningitis caused by multidrug-resistant Mycobacterium tuberculosis with intrathecal levofloxacin and amikacin: case report. | 2001 Feb 15 |
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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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Review of 49 neonates with acquired fungal sepsis: further characterization. | 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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Changes in electrovestibular brainstem responses after aminoglycoside intoxication in guinea pigs. | 2001 Jul |
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Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii. | 2001 Jul |
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Intravitreal antibiotics: the emergency kit. | 2001 Jul |
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Treatment and outcome of nocardia keratitis. | 2001 Jul |
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Penetration of amikacin into aqueous humor of rabbits. | 2001 Jul-Aug |
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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 |
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In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals. | 2001 Jun |
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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 |
|
Blood stream infections in a medical intensive care unit: spectrum and antibiotic susceptibility pattern. | 2001 Jun |
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[Neonatal bacterial infections at the CUH of Dakar]. | 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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Madura foot: treatment of Nocardia nova infection with antibiotics alone. | 2001 Jun |
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The early bactericidal activity of amikacin in pulmonary tuberculosis. | 2001 Jun |
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Translimbal approach for intravitreal injection in endophthalmitis after phacoemulsification. | 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 |
|
Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis. | 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 |
|
Study on antimicrobial susceptibility of bacteria causing neonatal infections: a 12 year study (1987-1998). | 2001 Mar |
|
Treatment of nosocomial postoperative pneumonia in cancer patients: a prospective randomized study. | 2001 Mar |
|
[Mycobacterium xenopi: epidemiological and bacteriological features]. | 2001 Mar-Apr |
|
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus]. | 2001 May |
|
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 |
|
Failure of treatment for chronic Mycobacterium abscessus meningitis despite adequate clarithromycin levels in cerebrospinal fluid. | 2001 Sep 1 |
|
A simple tool for monitoring nebulized amikacin treatments based on a single urine assay. | 2001 Spring |
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.
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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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WHO-VATC |
QJ01GB06
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LIVERTOX |
37
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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 |
342011
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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
Created by
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Code System | Code | Type | Description | ||
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AMIKACIN
Created by
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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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PRIMARY | |||
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157
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PRIMARY | |||
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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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PRIMARY | |||
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D000583
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PRIMARY | |||
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3583
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PRIMARY | |||
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37517-28-5
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PRIMARY | |||
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253-538-5
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84319SGC3C
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PRIMARY | |||
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37768
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1019508
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PRIMARY | USP-RS | ||
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Amikacin
Created by
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PRIMARY | |||
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SUB05431MIG
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3492
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PRIMARY | |||
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641
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PRIMARY | RxNorm | ||
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DB00479
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PRIMARY | |||
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M1670
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)