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

SMILES

[H][C@]3(O[C@H]1[C@@H](C[C@H](N)[C@@H](O[C@@]2([H])O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O)NC(=O)[C@@H](O)CCN)O[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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
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 8,297		5.27 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pneumonia 90	Curative	Phase III 656	Unknown
Cystic fibrosis 120	Primary	Phase III 656	Unknown
Sepsis 71	Curative	Approved 8,429	AMIKACIN SULFATE
Meningitis 18	Curative	Approved 8,429	AMIKACIN SULFATE
Urinary tract infections 205	Curative	Approved 8,429	AMIKACIN SULFATE

C_max

Value	Dose	Co-administered	Analyte	Population
2.8 μg/mL	590 mg 1 times / day steady-state, respiratory		AMIKACIN serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
23.5 μg × h/mL	590 mg 1 times / day steady-state, respiratory		AMIKACIN serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.9 h	590 mg 1 times / day steady-state, respiratory		AMIKACIN serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
90%	590 mg 1 times / day steady-state, respiratory		AMIKACIN serum	Homo sapiens

Doses

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Dose	Population	Adverse events
15 mg/kg single, intravenous Highest studied dose	healthy, 21-30 years
60 mg/kg single, respiratory Highest studied dose	healthy, 21-30 years
590 mg 1 times / day multiple, respiratory Recommended	unhealthy, 58.0 years (range: 16 - 61 years)	Disc. AE: Infective exacerbation of bronchiectasis, Dyspnea...
15 mg/kg 1 times / day multiple, intramuscular Highest studied dose	unhealthy, adult
590 mg 1 times / day multiple, respiratory Recommended	unhealthy, adult	Other AEs: Hypersensitivity pneumonitis, Hemoptysis...

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AEs

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AE	Significance	Dose	Population
Cough	1 patient Disc. AE	590 mg 1 times / day multiple, respiratory Recommended	unhealthy, 58.0 years (range: 16 - 61 years)
Oropharyngeal pain	1 patient Disc. AE	590 mg 1 times / day multiple, respiratory Recommended	unhealthy, 58.0 years (range: 16 - 61 years)
Pneumonia	1 patient Disc. AE	590 mg 1 times / day multiple, respiratory Recommended	unhealthy, 58.0 years (range: 16 - 61 years)
Respiratory disorder	1 patient Disc. AE	590 mg 1 times / day multiple, respiratory Recommended	unhealthy, 58.0 years (range: 16 - 61 years)
Dyspnea	4.5% Disc. AE	590 mg 1 times / day multiple, respiratory Recommended	unhealthy, 58.0 years (range: 16 - 61 years)

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2637	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2637
ChemicalBook	CB8146049	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8146049
eMolecules	36519241	https://www.emolecules.com/cgi-bin/more?vid=36519241
MolPort	MolPort-000-761-900	https://www.molport.com/shop/molecule-link/MolPort-000-761-900
ZINC	ZINC000008214483	http://zinc15.docking.org/substances/ZINC000008214483

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PubMed

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Title	Date	PubMed
Amikacin therapy of infections in neutropenic patients.	1975 Nov-Dec	1108649
[Multifocal invasive Kingella kingae infection].	1998 Feb	10223137
Amykacin-related apneic episode in an infant on peritoneal dialysis.	2000 Apr	10775086
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.	2000 Feb 1	10609550
Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis.	2001	11510269

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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
Record UNII	84319SGC3C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMIKACIN

Official Name

English

AMIKACIN [USP MONOGRAPH]

Common Name

English

AMIKACIN [VANDF]

Common Name

English

AMIKACIN [JAN]

Common Name

English

LUKADIN

Common Name

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175477

PART 522 IMPLANTATION OR INJECTABLE DOSAGE FORM NEW ANIMAL DRUGS

CFR

21 CFR 522.56

Other antibiotics for topical use

WHO-ATC

D06AX12

Designated/Approved

FDA ORPHAN DRUG

342011

Other aminoglycosides

WHO-VATC

QJ01GB06

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Code System

Code

Type

Description

WHO INTERNATIONAL PHARMACOPEIA

AMIKACIN

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.

NCI_THESAURUS

C61615

PRIMARY

DRUG CENTRAL

157

PRIMARY

WIKIPEDIA

AMIKACIN

PRIMARY

ChEMBL

CHEMBL177

PRIMARY

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Related Record

Type

Details


					N6M33094FD

AMIKACIN SULFATE

SALT/SOLVATE -> PARENT


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

[<11] % (average)

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Related Record

Type

Details


					2Z3NQ8MG2T

4-AMINO-2-HYDROXYBUTYRIC ACID, (S)-(-)-

IMPURITY -> PARENT


					EQK9Q303C5

KANAMYCIN A

IMPURITY -> PARENT

Comments:

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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Related Record

Type

Details


					84319SGC3C

AMIKACIN

ACTIVE MOIETY

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Name	Property Type	Amount
Volume of Distribution	PHARMACOKINETIC	0.34 Liters/Kilogram (average)

Biological Half-life	PHARMACOKINETIC	[2 to 3] hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound