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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
Structure of AMIKACIN SULFATE

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

HIDE SMILES / InChI

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

Description

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

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Molecular diagnosis of a Mycobacterium chelonae infection.
2001
Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium.
2001 Apr
Pharmacokinetics of amikacin after single intravenous and intramuscular administration in calves.
2001 Apr
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
Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis.
2001 Aug
Optimizing antibiotic therapy in the intensive care unit setting.
2001 Aug
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
Patents

Sample Use Guides

In Vivo Use Guide
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
Amikacin had a strong bactericidal effect on coccoid bacteria at 8 ug/mL concentration.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:49:20 UTC 2019
Edited
by admin
on Mon Oct 21 20:49:20 UTC 2019
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 [USP]
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 [WHO-IP]
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 [EP]
Common Name English
AMIKACIN SULPHATE
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 (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
AMIKACIN SULFATE [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 458114
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
EU-Orphan Drug EU/3/06/387
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
NCI_THESAURUS C2363
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
AMIKACIN SULFATE
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
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 Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY
NCI_THESAURUS
C230
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY
PUBCHEM
38351
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY
CAS
39831-55-5
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY
ChEMBL
CHEMBL177
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY
RXCUI
643
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M1670
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY Merck Index
EVMPD
SUB00444MIG
Created by admin on Mon Oct 21 20:49:21 UTC 2019 , Edited by admin on Mon Oct 21 20:49:21 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
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.
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC