Structure via PubChem · Public domain (PubChem)
tetrabenazine
Sign in to saveAlso known as Nitoman®, Revocon®, Ro-19569, TBZ, 2-oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizine, 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
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 US Food and Drug Administration (FDA) 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 United States. The compound has been known since the 1950s.
Key facts
- Drug.synonyms
- Ro-1-9569
- Drug.verifiedrevid
- 470603336
- Drug.IUPAC_name
- (SS,RR)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
- Drug.image
- Tetrabenazine.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Tetrabenazine3d.png
- Drug.image_class2
- bg-transparent
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Xenazine, Xentra, Nitoman, others
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- Low, extensive first pass effect
- Drug.protein_bound
- 82–85%
- Drug.metabolism
- Liver (CYP2D6-mediated)
- Drug.elimination_half life
- 10 hours parent compound (2 to 8 hours active metabolites)
via Wikipedia infobox
Chemical data
- Formula
- C19H27NO3
- Molecular weight
- 317.4 g/mol
- IUPAC name
- 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
- SMILES
- CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1=O)OC)OC
- InChIKey
- MKJIEFSOBYUXJB-UHFFFAOYSA-N
- XLogP
- 2.9
- Polar surface area
- 38.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
1,887 papers- Tetrabenazine.Expert opinion on pharmacotherapy · 2009
- Synthesis of Tetrabenazine and Its Derivatives, Pursuing Efficiency and Selectivity.Molecules (Basel, Switzerland) · 2020
- Deuterium Tetrabenazine for Tardive Dyskinesia.Clinical schizophrenia & related psychoses · 2018
- Tetrabenazine.Nature reviews. Drug discovery · 2009
- Tetrabenazine (Xenazine) for Huntington's chorea.The Medical letter on drugs and therapeutics · 2009
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 317.199094
- Has use
- medication
Show 8 more facts
- defined daily dose
- 0.1
- chemical formula
- C₁₉H₂₇NO₃
- canonical SMILES
- CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1=O)OC)OC
- Commons category
- Tetrabenazine
- subject has role
- adrenergic uptake inhibitors
- medical condition treated
- Huntington's disease
- physically interacts with
- Solute carrier family 18 member A2
- significant drug interaction
- phenelzine
via Wikidata · CC0
~6 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Adverse effects
- Black box warning
- Pharmacology
- Research
- Animal model of motivational dysfunction
- Dyskinetic cerebral palsy
- See also
- References
- External links
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 US Food and Drug Administration (FDA) 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 United States. The compound has been known since the 1950s.
==Medical uses== Tetrabenazine is used as a treatment, but not as a cure, for hyperkinetic disorders such as: Huntington's disease – specifically, the chorea associated with it Tourette syndrome and other tic disorders Tardive dyskinesia, a serious and sometimes irreversible side effect of long-term use of many antipsychotics, mainly typical antipsychotics Hemiballismus, spontaneous flinging limb movements due to contra-lateral subthalamic nucleus damage
Excerpted from Wikipedia’s “tetrabenazine” article, available under the CC BY-SA 4.0 licence.