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tetrabenazine

Trade name: xenazine

Small moleculeapprovedOrphan Drug FDA

Approved

Aug 15, 2008

(+)-alpha-Dihydrotetrabenazine (HTBZ) is an active component of tetrabenazine. Tetrabenazine is a mixture of closely-related compounds (isomers) and is readily metabolized in the human body to HTBZ and related isomers. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder and is marketed under the trade names Nitoman in Canada and Xenazine in New Zealand and some parts of Europe, and is also available in the USA as an orphan drug. (+)-alpha-Dihydrotetrabenazine and related benzo[a]quinolizines have been labeled with tritium and carbon-11 radioisotopes and used for in vitro and in vivo studies of the VMAT2 in animal and human brain. Adeptio Pharmaceuticals is developing alpha-dihydrotetrabenazine (HTBZ) for the treatment of neurological disorders. It acts by inhibiting vesicular monoamine transporter 2 (VMAT2), thereby blocking the transport of dopamine into axon terminals or into storage vesicles. — NCATS

Clinical trial activity

12 trials · 16 clinical orgs · 19 marketing orgs

Phase 1
3
Phase 2
4
Phase 3
3
Phase 4
3

Earliest trial started Jun 1, 1989 (NCT00642057)

Timeline

1990s

  1. Dec 11, 1997

    Orphan Drug Designation

2000s

  1. Jan 1, 2005

    Prestwick Pharmaceuticals — Earliest Phase 3 Sponsor(trial)

  2. Aug 15, 2008

    Prestwick Pharmaceuticals — Earliest FDA Approval

  3. Aug 15, 2008

    Bausch Health Companies — NDA Secondary Org

  4. Aug 15, 2008

    Bausch Health Companies — Marketing Organization

  5. Aug 15, 2008

    Prestwick Pharmaceuticals — NDA Organization

2010s

  1. Jan 1, 2011

    Bausch Health Companies — Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2015

    Dr. Reddy's Laboratories — Earliest Phase 1 Sponsor(trial)

  3. Aug 17, 2015

    Sun Pharmaceuticals — Marketing Organization

  4. Feb 3, 2016

    Hetero Labs Ltd — Marketing Organization

  5. Jan 31, 2017

    Apicore — Marketing Organization

  6. Jan 31, 2017

    Mylan — Marketing Organization

  7. Jul 7, 2017

    Actavis — Marketing Organization

  8. Jul 7, 2017

    Allergan PLC (2015) — Marketing Organization

  9. Dec 18, 2017

    Bionpharma Inc — Marketing Organization

  10. Jan 8, 2018

    Dr. Reddy's Laboratories — Marketing Organization

  11. Apr 20, 2018

    Lupin — Marketing Organization

  12. Apr 20, 2018

    Chartwell Pharmaceuticals — Marketing Organization

  13. Apr 8, 2019

    West-Ward Pharmaceutical — Marketing Organization

  14. Apr 8, 2019

    Hikma — Marketing Organization

2020s

  1. Jan 22, 2020

    Piramal — Marketing Organization

  2. Jan 22, 2020

    SLATE RUN PHARMA — Marketing Organization

  3. Jan 22, 2020

    Adaptis Pharma — Marketing Organization

  4. Mar 17, 2020

    Apotex — Marketing Organization

  5. Dec 4, 2020

    Ajanta Pharma Ltd — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewAug 15, 2008

Chemistry & pharmacology

Loading structure…

SMILES

COC1=C(OC)C=C2[C@H]3C[C@@H](O)[C@H](CC(C)C)CN3CCC2=C1
Mol. weight
319.4385 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Black box warning

Sources

Also known as

  • 1,2,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-2h-benzo[a]quinolizin-2-one
  • 1,2,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-2h-benzo[a]quinolizin-2-one
  • 2-oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bh-benzo[a]quinolizine
  • 2-oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bh-benzo[a]quinolizine
  • 2-oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-benzoquinolizine
  • 2-oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-benzoquinolizine
  • choreazine
  • choreazine
  • choreazine
  • choreazine
  • choreazine
  • choreazine
  • nitoman
  • nitoman
  • revocon
  • revocon
  • ro-19569
  • ro-19569
  • rubigen
  • tetmodis
  • tetrabenazina
  • tetrabenazina
  • tetrabenazine
  • tetrabenazine
  • tetrabenazine
  • tetrabenazine
  • tetrabenazine
  • tetrabenazine
  • tetrabenazine
  • tetrabenazine
  • (+/-)-tetrabenazine
  • tetrabenazine d6
  • tetrabenazinum
  • tetrabenazinum
  • xenazine
  • xenazine
  • xenazine
  • xenazine
  • xenazine 25

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT02844179Phase 1Jul 1, 2016Adeptio Pharmaceuticals, University of Michigan
NCT03702855Phase 1Dec 31, 2015Accutest Research Laboratories (I) Pvt. Ltd., Dr. Reddy's Laboratories
NCT03696329Phase 1Oct 31, 2015Accutest Research Laboratories (I) Pvt. Ltd., Dr. Reddy's Laboratories
NCT02509793Phase 4Apr 1, 2014Lundbeck, University of Texas at Houston
NCT01834911Phase 4Mar 1, 2013New York Medical College
NCT01543321Phase 3Mar 1, 2012University of Picardie Jules Verne
NCT01133353Phase 2Mar 1, 2011Bausch Health Companies
NCT00632645Phase 3Apr 1, 2009University of Paris
NCT04523935Phase 4Dec 7, 2005Sathbhavana Brain Clinic
NCT00219804Phase 3Sep 14, 2005Huntington Study Group, Prestwick Pharmaceuticals
NCT00362804N/AFeb 1, 2002Stanley Medical Research Institute, University of Toronto
NCT00642057N/AJun 1, 1989Baylor University
Showing 12 of 12 trials
Page 1 / 1

Organizations

Research & Development (16)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Accutest Research Laboratories (I) Pvt. Ltd.For profit2012015
Dr. Reddy's LaboratoriesFor profit2212015
Adeptio PharmaceuticalsFor profit1012016
Bausch Health CompaniesFor profit1112011
Baylor UniversityAcademic/Hospital1111989
Huntington Study GroupAcademic/Hospital1012005
LundbeckFor profit1012014
New York Medical CollegeAcademic/Hospital1112013
Prestwick PharmaceuticalsFor profit1112005
Sathbhavana Brain ClinicAcademic/Hospital1112005
Stanley Medical Research InstituteAcademic/Hospital1012002
University of MichiganAcademic/Hospital1112016
University of ParisAcademic/Hospital1112009
University of Picardie Jules VerneAcademic/Hospital1112012
University of Texas at HoustonAcademic/Hospital1112014
University of TorontoAcademic/Hospital1112002
16 organizations
Page 1 / 1

Marketing (24)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGJul 7, 2017
Adaptis PharmaFor profitMKTGJan 22, 2020
Ajanta Pharma LtdFor profitMKTGDec 4, 2020
Allergan PLC (2015)For profitMKTGJul 7, 2017
ApicoreFor profitMKTGJan 31, 2017
ApotexFor profitMKTGMar 17, 2020
Bausch Health CompaniesFor profitNDA2Aug 15, 2008
Bausch Health CompaniesFor profitMKTGAug 15, 2008
Bionpharma IncFor profitMKTGDec 18, 2017
Bionpharma IncFor profitSYNDec 18, 2017
Chartwell PharmaceuticalsFor profitMKTGApr 20, 2018
Dr. Reddy's LaboratoriesFor profitMKTGJan 8, 2018
Dr. Reddy's LaboratoriesFor profitSYNJan 8, 2018
Hetero Labs LtdFor profitMKTGFeb 3, 2016
HikmaFor profitMKTGApr 8, 2019
HikmaFor profitSYNApr 8, 2019
LupinFor profitMKTGApr 20, 2018
MylanFor profitMKTGJan 31, 2017
PiramalFor profitMKTGJan 22, 2020
Prestwick PharmaceuticalsFor profitNDAAug 15, 2008
SLATE RUN PHARMAFor profitMKTGJan 22, 2020
Sun PharmaceuticalsFor profitMKTGAug 17, 2015
Sun PharmaceuticalsFor profitSYNAug 17, 2015
West-Ward PharmaceuticalFor profitMKTGApr 8, 2019