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Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO3
Molecular Weight 317.4226
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRABENAZINE

SMILES

COC1=CC2=C(C=C1OC)[C@@H]3CC(=O)[C@@H](CC(C)C)CN3CC2

InChI

InChIKey=MKJIEFSOBYUXJB-HOCLYGCPSA-N
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/t14-,16-/m0/s1

HIDE SMILES / InChI

Description

Tetrabenazine (trade name Xenazine) is a monoamine depleter and used as the symptomatic treatment of chorea associated with Huntington's disease. Tetrabenazine is a reversible human vesicular monoamine transporter type 2 inhibitor (Ki = 100 nM). It acts within the basal ganglia and promotes depletion of monoamine neurotransmitters serotonin, norepinephrine, and dopamine from stores. It also decreases uptake into synaptic vesicles. Dopamine is required for fine motor movement, so the inhibition of its transmission is efficacious for hyperkinetic movement. Tetrabenazine exhibits weak in vitro binding affinity at the dopamine D2 receptor. The most common adverse reactions, which have occurred in at least 10% of subjects in studies and at least 5% greater than in subjects who received placebo, have been: sedation or somnolence, fatigue, insomnia, depression, suicidal thoughts, akathisia, anxiety, and nausea.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Behavior pharmacology of maprotiline, a new antidepressant].
1975 Nov
Tetrabenazine in the treatment of Huntington's chorea.
1976 Apr 17
Adenosine release in morphine-induced hypotension in rats.
1992 Jan
Expression cloning of a reserpine-sensitive vesicular monoamine transporter.
1992 Nov 15
Dyskinesia: L-dopa-induced and tardive dyskinesia.
2001 Nov-Dec
Evaluation of the central properties of several Hypericum species from the Canary Islands.
2002 Dec
Tetrabenazine fails to antagonize a behavioral effect of cocaine in rhesus monkeys.
2002 Jan-Feb
Effect of tetrabenazine on the striatal uptake of exogenous L-DOPA in vivo: a PET study in young and aged rhesus monkeys.
2002 Jun 15
Elevated platelet vesicular monoamine transporter density in untreated patients diagnosed with major depression.
2002 Nov 15
Tetrabenazine treatment for Huntington's disease-associated chorea.
2002 Nov-Dec
Catastrophic reactions induced by tetrabenazine.
2002 Sep
Lack of effect of testosterone and dihydrotestosterone compared to 17beta-oestradiol in 1-methyl-4-phenyl-1,2,3,6, tetrahydropyridine-mice.
2002 Sep
Non-synaptic release of [3H]noradrenaline in response to oxidative stress combined with mitochondrial dysfunction in rat hippocampal slices.
2003
Huntington's disease: prospects for neuroprotective therapy 10 years after the discovery of the causative genetic mutation.
2003 Aug
Increased ventral striatal monoaminergic innervation in Tourette syndrome.
2003 Aug 12
[11C]DTBZ-PET correlates of levodopa responses in asymmetric Parkinson's disease.
2003 Dec
Classification and treatment of tardive syndromes.
2003 Jan
VMAT2 binding is elevated in dopa-responsive dystonia: visualizing empty vesicles by PET.
2003 Jul
Obstructive sleep apnea is related to a thalamic cholinergic deficit in MSA.
2003 Jul 8
Tetrabenazine in the treatment of severe pediatric chorea.
2003 Jun
Successful therapy of tardive dyskinesia in a 71-year-old woman with a combination of tetrabenazine, olanzapine and tiapride.
2003 Mar
Decreased limbic vesicular monoamine transporter 2 in a genetic rat model of depression.
2003 Mar 7
Assessment of neuroimaging techniques as biomarkers of the progression of Parkinson's disease.
2003 Nov
Apparent opposite effects of tetrabenazine and reserpine on the toxic effects of 1-methyl-4-phenylpyridinium or 6-hydroxydopamine on nigro-striatal dopaminergic neurons.
2003 Nov 7
Escalating dose methamphetamine pretreatment alters the behavioral and neurochemical profiles associated with exposure to a high-dose methamphetamine binge.
2003 Oct
Endogenous 5-HT, released by MDMA through serotonin transporter- and secretory vesicle-dependent mechanisms, reduces hippocampal excitatory synaptic transmission by preferential activation of 5-HT1B receptors located on CA1 pyramidal neurons.
2003 Sep
Behavioural effects of thieno and pyrazolo [2,1] benzothiazepine derivatives in mice.
2004
PET studies and physiopathology of motor fluctuations in Parkinson's disease.
2004 Aug
Long-term reproducibility of in vivo measures of specific binding of radioligands in rat brain.
2004 Jul
Behavioral and neurochemical consequences of long-term intravenous self-administration of MDMA and its enantiomers by rhesus monkeys.
2004 Jul
The effect of rare human sequence variants on the function of vesicular monoamine transporter 2.
2004 Sep
Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters.
2004 Sep
Management of the extrapyramidal syndrome in chronic acquired hepatocerebral degeneration (CAHD).
2005 Aug
PET in LRRK2 mutations: comparison to sporadic Parkinson's disease and evidence for presymptomatic compensation.
2005 Dec
The role of radiotracer imaging in Parkinson disease.
2005 Jan 25
11C-DTBZ and 18F-FDG PET measures in differentiating dementias.
2005 Jun
The influence of measurement uncertainties on the evaluation of the distribution volume ratio and binding potential in rat studies on a microPET R4: a phantom study.
2005 Jun 21
Antidepressant properties of some Hypericum canariense L. and Hypericum glandulosum Ait. extracts in the forced swimming test in mice.
2005 Mar 21
Emerging drugs in Tourette syndrome.
2005 May
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects.
2005 Nov
Platelet vesicular monoamine transporter density in untreated patients diagnosed with social phobia.
2005 Sep 15
Pharmacological management of Huntington's disease: an evidence-based review.
2006
Dose-dependent improvement of myoclonic hyperkinesia due to Valproic acid in eight Huntington's Disease patients: a case series.
2006 Feb 28
Tetrabenazine in the treatment of hyperkinetic movement disorders.
2006 Jan
Tetrabenazine versus placebo for chorea in Huntington's disease.
2006 Jul
Longitudinal noninvasive PET-based beta cell mass estimates in a spontaneous diabetes rat model.
2006 Jun
Huntington's Disease.
2006 May
Interaction of amphetamines and related compounds at the vesicular monoamine transporter.
2006 Oct
Positron emission tomography of monoaminergic vesicular binding in aging and Parkinson disease.
2006 Sep
Preparation and evaluation of tetrabenazine enantiomers and all eight stereoisomers of dihydrotetrabenazine as VMAT2 inhibitors.
2011 May
Patents
Name Type Language
TETRABENAZINE
DASH   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
2H-BENZO(A)QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3R,11BR)-REL-
Common Name English
RO-1-9569
Code English
TETRABENAZINE [WHO-DD]
Common Name English
RO-19569
Code English
1,3,4,6,7,11B-HEXAHYDRO-3-ISOBUTYL-9,10-DIMETHOXY-2H-BENZO(A)QUINOLIZIN-2-ONE
Common Name English
XENAZINE
Brand Name English
TETRABENAZINE [INN]
Common Name English
TETRABENAZINE [ORANGE BOOK]
Common Name English
TETRABENAZINE [VANDF]
Common Name English
NITOMAN
Brand Name English
TETRABENAZINE [MI]
Common Name English
RO 1-9569
Code English
TETRABENAZINE [MART.]
Common Name English
NSC-169886
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 108897
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
FDA ORPHAN DRUG 109797
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
WHO-VATC QN07XX06
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
LIVERTOX 945
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
NDF-RT N0000190856
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
NCI_THESAURUS C471
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
FDA ORPHAN DRUG 278109
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
WHO-ATC N07XX06
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
Code System Code Type Description
MESH
D013747
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
MERCK INDEX
M10596
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY Merck Index
CAS
58-46-8
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
RXCUI
10390
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C81095
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
DRUG BANK
DB04844
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
PUBCHEM
11634155
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
IUPHAR
4834
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
EVMPD
SUB10939MIG
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-383-6
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
ChEMBL
CHEMBL117785
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
WIKIPEDIA
TETRABENAZINE
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
EPA CompTox
58-46-8
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
INN
1056
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY
NDF-RT
N0000190855
Created by admin on Mon Oct 21 20:32:28 UTC 2019 , Edited by admin on Mon Oct 21 20:32:28 UTC 2019
PRIMARY Vesicular Monoamine Transporter 2 Inhibitors [MoA]