Tetrabenazine

Tetrabenazine
Clinical data
Trade namesXenazine, Xentra, Nitoman, others
Other namesRo-1-9569
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow, extensive first pass effect
Protein binding82–85%
MetabolismLiver (CYP2D6-mediated)
Elimination half-life10 hours parent compound (2 to 8 hours active metabolites)[3]
ExcretionKidney (~75%) and fecal (7–16%)[4]
Identifiers
  • (SS,RR)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.348 Edit this at Wikidata
Chemical and physical data
FormulaC19H27NO3
Molar mass317.429 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C3C(CC(C)C)CN2C(c1c(cc(OC)c(OC)c1)CC2)C3
  • InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3 checkY
  • Key:MKJIEFSOBYUXJB-UHFFFAOYSA-N checkY
  (verify)

Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorders. It is sold under the brand names Nitoman and Xenazine among others. On August 15, 2008, the U.S. Food and Drug Administration approved the use of tetrabenazine to treat chorea associated with Huntington's disease. Although other drugs had been used "off label," tetrabenazine was the first approved treatment for Huntington's disease in the U.S.[5] The compound has been known since the 1950s.

  1. ^ "TETRABENAZINE RAN/TETRABENAZINE SUN/TETRABENAZINE RBX (Sun Pharma ANZ Pty Ltd)". Therapeutic Goods Administration.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ Yero T, Rey JA (December 2008). "Tetrabenazine (Xenazine), An FDA-Approved Treatment Option For Huntington's Disease-Related Chorea". P & T. 33 (12): 690–694. PMC 2730806. PMID 19750050.
  4. ^ "Xenazine (tetrabenazine) Tablets, for Oral Use. Full Prescribing Information. Revised: 6/2015" (PDF). H. Lundbeck A/S. Retrieved 9 December 2015.
  5. ^ 1st US drug for Huntington's disease wins approval [dead link]