Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H43N5O13.2H2O4S |
| Molecular Weight | 781.759 |
| Optical Activity | ( - ) |
| 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 | |
| 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 | |
| Defined Stereocenters | 16 / 16 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Amikacin therapy of infections in neutropenic patients. | 1975 Nov-Dec |
|
| 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 |
|
| Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis. | 2001 |
|
| [Criteria of low risk of mortality in children with neutropenia and fever during cancer chemotherapy]. | 2001 |
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| Molecular diagnosis of a Mycobacterium chelonae infection. | 2001 |
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| Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium. | 2001 Apr |
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| Pharmacokinetics of amikacin after single intravenous and intramuscular administration in calves. | 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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| Optimizing antibiotic therapy in the intensive care unit setting. | 2001 Aug |
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| Once-a-day individualized amikacin dosing for suspected infection at birth based on population pharmacokinetic models. | 2001 Aug |
|
| Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica. | 2001 Aug |
|
| [Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
|
| [Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa]. | 2001 Feb |
|
| 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 |
|
| Single-daily ceftriaxone plus amikacin versus thrice-daily ceftazidime plus amikacin as empirical treatment of febrile neutropenia in children with cancer. | 2001 Feb |
|
| Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations. | 2001 Feb |
|
| Novel treatment of meningitis caused by multidrug-resistant Mycobacterium tuberculosis with intrathecal levofloxacin and amikacin: case report. | 2001 Feb 15 |
|
| Objective method for differentiating between drug-induced vestibulotoxicity and cochleotoxicity. | 2001 Jan |
|
| [Stab wound of the spinal cord complicated by meningitis and subarachnoid fistula]. | 2001 Jan |
|
| 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 |
|
| Use of a recombinant strain of Mycobacterium avium expressing beta-galactosidase to evaluate the activities of antimycobacterial agents inside macrophages. | 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 |
|
| Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii. | 2001 Jul |
|
| Treatment and outcome of nocardia keratitis. | 2001 Jul |
|
| Penetration of amikacin into aqueous humor of rabbits. | 2001 Jul-Aug |
|
| 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 |
|
| Cost-effectiveness of cefepime + netilmicin or ceftazidime + amikacin or meropenem monotherapy in febrile neutropenic children with malignancy in Turkey. | 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 |
|
| 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 |
|
| [Clinical analysis of neutropenic fever associated with hematological disorders]. | 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 |
|
| 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 |
|
| Bacterial isolates from blood and their susceptibility patterns in critically ill foals: 543 cases (1991-1998). | 2001 May 15 |
|
| 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
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Oct 21 20:49:20 UTC 2019
by
admin
on
Mon Oct 21 20:49:20 UTC 2019
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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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| Classification Tree | Code System | Code | ||
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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
Created by
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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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C230
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38351
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39831-55-5
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CHEMBL177
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643
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M1670
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PRIMARY | Merck Index | ||
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SUB00444MIG
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PARENT -> SALT/SOLVATE |
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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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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Volume of Distribution | PHARMACOKINETIC |
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