tigecycline

Trade name: tygacil

Small moleculeapproved

Approved

Jun 15, 2005

Tigecycline (INN) is an antibiotic used to treat a number of bacterial infections. It is a first in class glycylcycline that is administered intravenously. For the treatment of infections caused by susceptible strains of the designated microorganisms in the following conditions: Complicated skin and skin structure infections caused by Escherichia coli, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus agalactiae, Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Streptococcus pyogenes and Bacteroides fragilis. Complicated intra-abdominal infections caused by Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Klebsiella oxytoca, Klebsiella pneumoniae, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Bacteroides fragilis, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides vulgatus, Clostridium perfringens, and Peptostreptococcus micros. Tigecycline, a glycylcycline, inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. Tigecycline carries a glycylamido moiety attached to the 9-position of minocycline. The substitution pattern is not present in any naturally occurring or semisynthetic tetracycline and imparts certain microbiologic properties to tigecycline. In general, tigecycline is considered bacteriostatic; however, TYGACIL has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila. In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterials. — NCATS

Clinical trial activity

49 trials · 48 clinical orgs · 14 marketing orgs

Phase 1
6
Phase 2
23
Phase 3
22
Phase 4
13

Earliest trial started Apr 1, 2002 (NCT00600600)

Timeline

2000s

  1. Jan 1, 2002

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2002

    Pfizer — Earliest Phase 3 Sponsor(trial)

  3. Jun 15, 2005

    Wyeth — Earliest FDA Approval

  4. Jun 15, 2005

    Wyeth — NDA Organization

  5. Jun 15, 2005

    Pfizer — NDA Secondary Org

  6. Jan 1, 2006

    Pfizer — Earliest Phase 1 Sponsor(trial)

2010s

  1. May 27, 2015

    Sandoz — Marketing Organization

  2. May 27, 2015

    Novartis — Marketing Organization

  3. Dec 1, 2016

    Fresenius — NDA Secondary Org

  4. Jan 18, 2018

    Accord Research — NDA Secondary Org

  5. Aug 2, 2018

    Amneal Pharmaceuticals — NDA Secondary Org

  6. Aug 2, 2018

    Amneal Pharmaceuticals — Marketing Organization

  7. Dec 21, 2018

    Apotex — Marketing Organization

  8. Jun 11, 2019

    Aurobindo Pharma — Marketing Organization

  9. Jun 11, 2019

    Eugia Pharma — Marketing Organization

  10. Oct 18, 2019

    Xellia Pharmaceuticals — Marketing Organization

  11. Oct 18, 2019

    Novo Nordisk — Marketing Organization

2020s

  1. May 13, 2021

    Eu Yan Sang — Marketing Organization

  2. May 13, 2021

    Meitheal — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedPriority reviewJun 15, 2005

Chemistry & pharmacology

Loading structure…

SMILES

CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(O)=C(NC(=O)CNC(C)(C)C)C=C4N(C)C
Mol. weight
585.6487 g/mol
Lipinski Ro5
3 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

No

Black box warning

Sources

Also known as

  • (4s,4as,5ar,12as)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
  • (4s,4as,5ar,12as)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
  • 9-(tert-butylglycylamido)minocycline
  • gar 936
  • gar-936
  • glycopeptide
  • glycopeptide
  • glycylcycline
  • tbg-mino
  • tigeciclina
  • tigeciclina
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecycline
  • tigecyclinum
  • tigecyclinum
  • tygacil
  • tygacil
  • tygacil
  • tygacil
  • tygacil
  • tygacil
  • way-gar-936
  • way-gar-936

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07089186Phase 3Apr 12, 2025Qilu Pharmaceutical Co., Ltd.
NCT06893835Phase 4Dec 1, 2024Beni Suef University
NCT07258225Phase 4Apr 1, 2024Government of Egypt
NCT06739382Phase 3Jan 1, 2021Beni Suef University, Cairo University
NCT03962920N/AMay 1, 2020University of Copenhagen
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
NCT04208763N/ADec 20, 2019Institute of Liver and Biliary Sciences, India
NCT04489459Phase 4Sep 21, 2019Al Azhar University
NCT04042077Phase 3Aug 31, 2019Hospital Agostino Gemelli, Menarini Group
NCT03950544Early Phase 1 (Phase 1)Jan 1, 2019Huazhong University of Science and Technology
NCT02800785N/AMay 1, 2016Cancer Research Network, University of California, Los Angeles, University of Washington
NCT01970371Phase 3Sep 1, 2014Achaogen, Inc., Department of Health and Human Services
NCT02191475Phase 2/Phase 3 (Phase 3)May 1, 2014Nanjing Medical University, Tianjin Medical University, Zhejiang Hisun Pharmaceutical Co. Ltd.
NCT02040818Phase 2/Phase 3 (Phase 3)Nov 1, 2013National Institutes of Health (NIH), University of California, San Diego
NCT01721408Phase 4Nov 1, 2012Pfizer
NCT01592032Phase 4May 1, 2012Clinica Universidad de Navarra
NCT01483872Phase 3Mar 1, 2012University of California, San Diego
NCT01560143Phase 4Mar 1, 2012Pfizer, University of Michigan
NCT00911573Phase 3Aug 1, 2011Pfizer
NCT01342731Phase 4Jul 1, 2011Mahidol University, Siriraj Hospital
Showing 20 of 49 trials
Page 1 / 3

Organizations

Research & Development (48)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
PfizerFor profit272552002
WyethFor profit20042002
Beni Suef UniversityAcademic/Hospital2222021
University of California, Los AngelesAcademic/Hospital2022011
University of California, San DiegoAcademic/Hospital2212012
University of CopenhagenAcademic/Hospital2122020
Achaogen, Inc.For profit1112014
Al Azhar UniversityAcademic/Hospital1112019
Baylor UniversityAcademic/Hospital1112006
Cairo UniversityAcademic/Hospital1012021
Cancer Research NetworkAcademic/Hospital1012016
Clinica Universidad de NavarraAcademic/Hospital1112012
Cornell UniversityAcademic/Hospital1012011
CPL AssociatesFor profit1112007
Cystic Fibrosis FoundationAcademic/Hospital1012020
Department of Health and Human ServicesGovernment1012014
Erasmus University RotterdamAcademic/Hospital1012020
Government of AustraliaGovernment1012020
Government of EgyptGovernment1112024
Griffith UniversityAcademic/Hospital1012020
48 organizations
Page 1 / 3

Marketing (17)

OrganizationOrg typeRelationshipDate
Accord ResearchFor profitNDA2Jan 18, 2018
Amneal PharmaceuticalsFor profitNDA2Aug 2, 2018
Amneal PharmaceuticalsFor profitMKTGAug 2, 2018
ApotexFor profitMKTGDec 21, 2018
ApotexFor profitSYNDec 21, 2018
Aurobindo PharmaFor profitMKTGJun 11, 2019
Eu Yan SangFor profitMKTGMay 13, 2021
Eugia PharmaFor profitMKTGJun 11, 2019
FreseniusFor profitNDA2Dec 1, 2016
MeithealFor profitMKTGMay 13, 2021
NovartisFor profitMKTGMay 27, 2015
Novo NordiskFor profitMKTGOct 18, 2019
PfizerFor profitNDA2Jun 15, 2005
SandozFor profitSYNMay 27, 2015
SandozFor profitMKTGMay 27, 2015
WyethFor profitNDAJun 15, 2005
Xellia PharmaceuticalsFor profitMKTGOct 18, 2019