AMIKACIN

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

Structure Search

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

HIDE SMILES / InChI

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
30S ribosomal protein S12 19	Inhibitor 7464	Cystic Fibrosis	5.27 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sepsis 39	Primary	30S ribosomal protein S12	Approved 7888	AMIKACIN SULFATE
Urinary Tract Infections 227	Primary	30S ribosomal protein S12	Approved 7888	AMIKACIN SULFATE
Cystic Fibrosis 125	Primary	30S ribosomal protein S12	Phase III 632
Meningitis 17	Primary	30S ribosomal protein S12	Approved 7888	AMIKACIN SULFATE
Pneumonia, Bacterial 33	Primary	30S ribosomal protein S12	Phase III 632
Bacterial endocarditis 6			Approved (off-label) 8
Cystic fibrosis 4			Approved (off-label) 8
Nocardiosis 3			Approved (off-label) 8
Tuberculosis 78			Approved (off-label) 8

PubMed

Title	Date	PubMed
[Multifocal invasive Kingella kingae infection].	1998 Feb	10223137
The aminoglycosides.	1999 May	10319086
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.	2000 Feb 1	10609550
Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution.	2001	11525351
Cutaneous nocardiosis of the chest wall and pleura--10-year consequences of a hand actinomycetoma.	2001	11306835
Molecular diagnosis of a Mycobacterium chelonae infection.	2001	11261816
The immunomodulatory effects of gentamicin, imipenem, piperacillin and amphotericin B on LAK effector function in vitro.	2001 Apr	11335146
Multiple nocardial abscesses of cerebrum, cerebellum and spinal cord, causing quadriplegia.	2001 Apr	11311481
[Combination therapy of antibiotics and intravenous immunoglobulin].	2001 Apr	11305006
Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis.	2001 Aug	11529290
Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica.	2001 Aug	11391480
[Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa].	2001 Feb	11265218
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	11248523
Efficacy of meropenem as monotherapy in the treatment of ventilator-associated pneumonia.	2001 Feb	11233804
Single-daily ceftriaxone plus amikacin versus thrice-daily ceftazidime plus amikacin as empirical treatment of febrile neutropenia in children with cancer.	2001 Feb	11168867
Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations.	2001 Feb	11165117
Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998).	2001 Feb 1	11201564
Novel treatment of meningitis caused by multidrug-resistant Mycobacterium tuberculosis with intrathecal levofloxacin and amikacin: case report.	2001 Feb 15	11181130
Objective method for differentiating between drug-induced vestibulotoxicity and cochleotoxicity.	2001 Jan	11314720
Carriage of class 1 integrons and antibiotic resistance in clinical isolates of Acinetobacter baumannii from northern Spain.	2001 Jan	11192508
Nosocomial pneumonia. Diagnostic and therapeutic considerations.	2001 Jan	11190353
Disseminated Mycobacterium abscessus infection manifesting as fever of unknown origin and intra-abdominal lymphadenitis: case report and literature review.	2001 Jan	11173189
Bilateral infectious keratitis after laser in situ keratomileusis: a case report and review of the literature.	2001 Jan	11150275
Review of 49 neonates with acquired fungal sepsis: further characterization.	2001 Jan	11134435
Use of a recombinant strain of Mycobacterium avium expressing beta-galactosidase to evaluate the activities of antimycobacterial agents inside macrophages.	2001 Jan	11120998
Granulocyte colony-stimulating factor in the treatment of high-risk febrile neutropenia: a multicenter randomized trial.	2001 Jan 3	11136839
Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii.	2001 Jul	11502379
Penetration of amikacin into aqueous humor of rabbits.	2001 Jul-Aug	11399939
Translimbal approach for intravitreal injection in endophthalmitis after phacoemulsification.	2001 Jun	11408123
Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test.	2001 Jun	11389111
Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis.	2001 Jun	11384583
Mycobacterium fortuitum wound infection following laparoscopy.	2001 Mar	11525156
Meningoencephalitis caused by Bacillus cereus in a neonate.	2001 Mar	11406681
[Clinical analysis of neutropenic fever associated with hematological disorders].	2001 Mar	11321778
Treatment of nosocomial postoperative pneumonia in cancer patients: a prospective randomized study.	2001 Mar	11258785
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.	2001 Mar	11247678
Hair cell regeneration and recovery of auditory thresholds following aminoglycoside ototoxicity in Bengalese finches.	2001 Mar	11223308
[Mycobacterium xenopi: epidemiological and bacteriological features].	2001 Mar-Apr	11282515
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus].	2001 May	11424487
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.	2001 May	11337225
Antibiotic selective pressure and development of bacterial resistance.	2001 May	11337221
Antimicrobial susceptibility of blood culture isolates of viridans streptococci: relationship to a change in empirical antibiotic therapy in febrile neutropenia.	2001 May	11328787
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.	2001 May-Jun	11419030
Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies.	2001 Sep	11532996
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	11442347

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 19:51:24 UTC 2019` Edited by `admin` on `Mon Oct 21 19:51:24 UTC 2019`
Record UNII	84319SGC3C
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AMIKACIN

Official Name

English

AMIKACIN [EP]

Common Name

English

AMIKACIN [VANDF]

Common Name

English

AMIKACIN [WHO-DD]

Common Name

English

AMIKACIN [JAN]

Common Name

English

LUKADIN

Common Name

English

AMIKACIN [WHO-IP]

Common Name

English

NSC-177001

Code

English

AMIKACIN [MART.]

Common Name

English

AMIKACIN [HSDB]

Common Name

English

AMIKACIN [USP]

Common Name

English

BAY 41-6551

Code

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

Common Name

English

AMIKACIN [MI]

Common Name

English

AMIKACIN [USP-RS]

Common Name

English

AMIKACINUM [WHO-IP LATIN]

Common Name

English

AMIKACIN [INN]

Common Name

English

POTENTOX

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)-

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175477