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amikacin

Trade name: Amikin

Small moleculeapproved

Approved

Jun 1, 1976

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. — NCATS

Clinical trial activity

73 trials · 84 clinical orgs · 17 marketing orgs

Phase 1
11
Phase 2
33
Phase 3
17
Phase 4
14

Earliest trial started Nov 2, 1999 (NCT00000796)

Timeline

1970s

  1. Jun 1, 1976

    Bristol-Myers — Earliest FDA Approval

  2. Jun 1, 1976

    Bristol-Myers — NDA Organization

1980s

  1. Jan 22, 1981

    Apothecon — Marketing Organization

1990s

  1. May 18, 1992

    West-Ward Pharmaceutical — Marketing Organization

  2. May 18, 1992

    Hikma — Marketing Organization

  3. Jul 30, 1993

    Hospira — Marketing Organization

  4. Sep 28, 1993

    Teva — Marketing Organization

  5. Sep 28, 1993

    Eu Yan Sang — Marketing Organization

  6. Sep 28, 1993

    Meitheal — Marketing Organization

  7. Oct 28, 1994

    Abbott — Marketing Organization

  8. Jan 1, 1999

    Earliest Phase 2 Sponsor(trial)

2000s

  1. Jan 1, 2004

    Insmed, Inc. — Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2007

    Earliest Phase 3 Sponsor(trial)

2010s

  1. Dec 12, 2013

    Emcure — Marketing Organization

  2. Dec 12, 2013

    Avet Lifesciences — Marketing Organization

  3. Dec 9, 2015

    Fresenius — Marketing Organization

  4. May 12, 2016

    Sagent Pharmaceuticals, Inc. — Marketing Organization

  5. Sep 28, 2018

    Insmed, Inc. — NDA Secondary Org

  6. Sep 28, 2018

    Merck — NDA Secondary Org

2020s

  1. Mar 19, 2024

    Qilu Pharmaceutical Co., Ltd. — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedJun 1, 1976

Chemistry & pharmacology

Loading structure…

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]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
Mol. weight
585.61 g/mol
Lipinski Ro5
3 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral, Topical
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

Yes

Black box warning

Sources

Also known as

  • 1-n-(l(-)-gamma-amino-alpha-hydroxybutyryl)kanamycin a
  • 1-n-(l(-)-gamma-amino-alpha-hydroxybutyryl)kanamycin a
  • amicacin
  • amicacin
  • amicacin
  • amiglyde
  • amiglyde
  • amiglyde-v
  • amiglyde-v
  • amikacillin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacin
  • amikacina
  • amikacina
  • amikacine
  • amikacine
  • amikacin hydrate
  • amikacin sulfate
  • amikacin sulfate
  • amikacin sulfate
  • amikacin sulfate
  • amikacin sulphate
  • amikacin sulphate
  • amikacinum
  • amikacinum
  • amikavet
  • amikavet
  • amikin
  • amikin
  • amikin
  • arikace
  • arikace
  • arikace
  • bb-k8
  • bb-k8
  • briclin
  • briclin
  • liposomal amikacin
  • liposomal amikacin
  • lukadin
  • o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1->4)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1->6))-n(3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine
  • o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1->4)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1->6))-n(3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07089186Phase 3Apr 12, 2025Qilu Pharmaceutical Co., Ltd.
NCT06808074Phase 4Feb 12, 2025Asian Institute of Gastroenterology
NCT06602557Phase 2Nov 15, 2024Assistance Publique - Hôpitaux de Paris
NCT06097767Early Phase 1 (Phase 1)Oct 19, 2023Al Azhar University
NCT05761405Early Phase 1 (Phase 1)Oct 16, 2023Ecole Polytechnique Fédérale de Lausanne, University of Bern, University of Lausanne
NCT05555303Phase 2Dec 31, 2022Institute of Tropical Medicine, Belgium, Rwanda Biomedical Centre, World Health Organization
NCT05213507Phase 3Mar 31, 2022Fudan University
NCT04948463Phase 4Jul 31, 2021Murdoch University
NCT06739382Phase 3Jan 1, 2021Beni Suef University, Cairo University
NCT04310930Phase 2/Phase 3 (Phase 3)Mar 31, 2020Cystic Fibrosis Foundation, Erasmus University Rotterdam, Government of Australia, Griffith University, James Cook University Hospital, Middlesbrough, UK, Monash University, Murdoch University, Newcastle University, South Australian Health and Medical Research Institute, University of Copenhagen, University of Manitoba, University of Melbourne, University of Paris, University of Queensland
NCT04249531Phase 1Feb 15, 2020University of Groningen
NCT04209192Phase 2Jan 1, 2020Instituto Nacional de Ciencias Medicas y Nutricion Salvador Zubiran, Laboratorios Senosiain, S.A. de C.V.
NCT04197739Phase 4Dec 31, 2019Tel Aviv University
NCT04178148N/ANov 30, 2019Centre Hospitalier Universitaire de Nīmes, University of Nimes
NCT03990467N/ASep 30, 2019University of Lyon
NCT04867993N/AAug 28, 2018Free University of Amsterdam, Katholieke Universiteit Leuven, Leiden University, University of Sarajevo, University of Tuzla
NCT03449459Early Phase 1 (Phase 1)Jul 31, 2018Fudan University, Guangzhou Medical University, Jiao Tong University
NCT03409679Phase 3Mar 23, 2018Polyphor Ltd.
NCT02975570Phase 3Aug 1, 2017Boston University, University of Florida, Westat
NCT03169114N/AAug 1, 2017Raja Isteri Pengiran Anak Saleha Hospital, RIPAS Hospital
Showing 20 of 73 trials
Page 1 / 4

Organizations

Research & Development (84)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Insmed, Inc.For profit111032004
BayerFor profit4422005
National Institute of Allergy and Infectious Diseases (NIAID)Government4331999
Nektar TherapeuticsFor profit4022005
Université catholique de LouvainAcademic/Hospital4322012
Cardeas PharmaFor profit3322013
Fudan UniversityAcademic/Hospital3322014
Katholieke Universiteit LeuvenAcademic/Hospital3222012
University of ParisAcademic/Hospital3232004
Boston UniversityAcademic/Hospital2122003
Cairo UniversityAcademic/Hospital2022014
Centre Hospitalier Universitaire de NīmesAcademic/Hospital2222014
Johnson and JohnsonFor profit2212015
Murdoch UniversityAcademic/Hospital2122020
Polyphor Ltd.For profit2222016
University of FloridaAcademic/Hospital2122010
Aix-University of MarseilleAcademic/Hospital1112017
Al Azhar UniversityAcademic/Hospital1112023
Asian Institute of GastroenterologyAcademic/Hospital1112025
Assistance Publique - Hôpitaux de ParisAcademic/Hospital1112024
84 organizations
Page 1 / 5

Marketing (19)

OrganizationOrg typeRelationshipDate
AbbottFor profitMKTGOct 28, 1994
ApotheconFor profitMKTGJan 22, 1981
ApotheconFor profitNDA2—
Avet LifesciencesFor profitMKTGDec 12, 2013
Bristol-MyersFor profitNDAJun 1, 1976
EmcureFor profitMKTGDec 12, 2013
Eu Yan SangFor profitMKTGSep 28, 1993
FreseniusFor profitMKTGDec 9, 2015
HikmaFor profitMKTGMay 18, 1992
HospiraFor profitMKTGJul 30, 1993
Insmed, Inc.For profitNDA2Sep 28, 2018
MeithealFor profitMKTGSep 28, 1993
MerckFor profitNDA2Sep 28, 2018
Qilu Pharmaceutical Co., Ltd.For profitMKTGMar 19, 2024
Sagent Pharmaceuticals, Inc.For profitMKTGMay 12, 2016
Sagent Pharmaceuticals, Inc.For profitSYNMay 12, 2016
Teligent PharmaceuticalsFor profitMKTG—
TevaFor profitMKTGSep 28, 1993
West-Ward PharmaceuticalFor profitMKTGMay 18, 1992