U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C19H27NO3
Molecular Weight 317.4226
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://reference.medscape.com/drug/xenazine-tetrabenazine-343075 | https://www.drugbank.ca/drugs/DB04844 | https://www.drugs.com/cdi/tetrabenazine.html

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
36.4 µM [Ki]
54.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XENAZINE

Approved Use

Tetrabenazine tablets are indicated for the treatment of chorea associated with Huntington's disease. Tetrabenazine tablets are a vesicular monoamine transporter 2 (VMAT) inhibitor indicated for the treatment of chorea associated with Huntington's disease. (1)

Launch Date

2008
Primary
XENAZINE

Approved Use

Tetrabenazine tablets are indicated for the treatment of chorea associated with Huntington's disease. Tetrabenazine tablets are a vesicular monoamine transporter 2 (VMAT) inhibitor indicated for the treatment of chorea associated with Huntington's disease. (1)

Launch Date

2008
Primary
XENAZINE

Approved Use

Tetrabenazine tablets are indicated for the treatment of chorea associated with Huntington's disease. Tetrabenazine tablets are a vesicular monoamine transporter 2 (VMAT) inhibitor indicated for the treatment of chorea associated with Huntington's disease. (1)

Launch Date

2008
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.66 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TETRABENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.45 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TETRABENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.13 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TETRABENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
14%
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TETRABENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Other AEs: Acute dystonia, Crisis oculogyric...
Other AEs:
Acute dystonia
Crisis oculogyric
Nausea and vomiting
Sweating
Sedation
Hypotension
Confusion
Diarrhea
Hallucinations
Redness
Tremor
Sources:
12.5 mg 1 times / day steady, oral
Recommended
Dose: 12.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 12.5 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Other AEs: Depression, Suicidal tendency...
AEs

AEs

AESignificanceDosePopulation
Acute dystonia
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Confusion
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Crisis oculogyric
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Diarrhea
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Hallucinations
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Hypotension
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Nausea and vomiting
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Redness
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Sedation
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Sweating
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Tremor
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
Depression
12.5 mg 1 times / day steady, oral
Recommended
Dose: 12.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 12.5 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Suicidal tendency
12.5 mg 1 times / day steady, oral
Recommended
Dose: 12.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 12.5 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive
no
no
no
no
no
no
no
no
no
no
no
no
no
no
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Preparation and evaluation of tetrabenazine enantiomers and all eight stereoisomers of dihydrotetrabenazine as VMAT2 inhibitors.
2011-05
Interaction of amphetamines and related compounds at the vesicular monoamine transporter.
2006-10
Positron emission tomography of monoaminergic vesicular binding in aging and Parkinson disease.
2006-09
Measurement of kinetically resolved vesicular dopamine uptake and efflux using rotating disk electrode voltammetry.
2006-07-15
Tetrabenazine versus placebo for chorea in Huntington's disease.
2006-07
Longitudinal noninvasive PET-based beta cell mass estimates in a spontaneous diabetes rat model.
2006-06
Huntington's Disease.
2006-05
Dose-dependent improvement of myoclonic hyperkinesia due to Valproic acid in eight Huntington's Disease patients: a case series.
2006-02-28
Tetrabenazine as antichorea therapy in Huntington disease: a randomized controlled trial.
2006-02-14
Tetrabenazine in the treatment of hyperkinetic movement disorders.
2006-01
A blessing in disguise: resolution of tardive dyskinesia with development of cervical myelitis.
2006-01
Pharmacological management of Huntington's disease: an evidence-based review.
2006
PET in LRRK2 mutations: comparison to sporadic Parkinson's disease and evidence for presymptomatic compensation.
2005-12
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects.
2005-11
Platelet vesicular monoamine transporter density in untreated patients diagnosed with social phobia.
2005-09-15
Management of the extrapyramidal syndrome in chronic acquired hepatocerebral degeneration (CAHD).
2005-08
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.
2005-06-21
11C-DTBZ and 18F-FDG PET measures in differentiating dementias.
2005-06
Emerging drugs in Tourette syndrome.
2005-05
Antidepressant properties of some Hypericum canariense L. and Hypericum glandulosum Ait. extracts in the forced swimming test in mice.
2005-03-21
Decreased platelet vesicular monoamine transporter density in habitual smokers.
2005-03
Decreased platelet vesicular monoamine transporter density in children and adolescents with attention deficit/hyperactivity disorder.
2005-03
The role of radiotracer imaging in Parkinson disease.
2005-01-25
Tetrabenazine treatment in movement disorders.
2004-12-17
Lack of regional selectivity during the progression of Parkinson disease: implications for pathogenesis.
2004-12
Identification of tissue-restricted transcripts in human islets.
2004-10
The effect of rare human sequence variants on the function of vesicular monoamine transporter 2.
2004-09
Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters.
2004-09
Adrafinil-induced orofacial dyskinesia.
2004-08
[Movement disorders in childhood: therapeutic update].
2004-08
PET studies and physiopathology of motor fluctuations in Parkinson's disease.
2004-08
Differential effects of scopolamine on in vivo binding of dopamine transporter and vesicular monoamine transporter radioligands in rat brain.
2004-08
Long-term reproducibility of in vivo measures of specific binding of radioligands in rat brain.
2004-07
Behavioral and neurochemical consequences of long-term intravenous self-administration of MDMA and its enantiomers by rhesus monkeys.
2004-07
Striatal monoamine terminals in Lewy body dementia and Alzheimer's disease.
2004-06
Electrochemical monitoring of transport by a vesicular monoamine transporter expressed in Xenopus oocytes.
2004-02-15
Behavioural effects of thieno and pyrazolo [2,1] benzothiazepine derivatives in mice.
2004
Dopamine transmission in DYT1 dystonia.
2004
Raclopride studies of dopamine release: dependence on presynaptic integrity.
2003-12-01
[11C]DTBZ-PET correlates of levodopa responses in asymmetric Parkinson's disease.
2003-12
Apparent opposite effects of tetrabenazine and reserpine on the toxic effects of 1-methyl-4-phenylpyridinium or 6-hydroxydopamine on nigro-striatal dopaminergic neurons.
2003-11-07
Assessment of neuroimaging techniques as biomarkers of the progression of Parkinson's disease.
2003-11
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.
2003-09
Increased ventral striatal monoaminergic innervation in Tourette syndrome.
2003-08-12
Huntington's disease: prospects for neuroprotective therapy 10 years after the discovery of the causative genetic mutation.
2003-08
Non-synaptic release of [3H]noradrenaline in response to oxidative stress combined with mitochondrial dysfunction in rat hippocampal slices.
2003
Self-biting induced by activation of L-type calcium channels in mice: dopaminergic influences.
2002-10-18
Expression cloning of a reserpine-sensitive vesicular monoamine transporter.
1992-11-15
Adenosine release in morphine-induced hypotension in rats.
1992-01
Tetrabenazine in the treatment of Huntington's chorea.
1976-04-17
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:43:38 GMT 2025
Edited
by admin
on Mon Mar 31 18:43:38 GMT 2025
Record UNII
Z9O08YRN8O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRABENAZINE
DASH   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
NITOMAN
Preferred 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 [JAN]
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 [WHO-DD]
Common Name English
TETRABENAZINE [ORANGE BOOK]
Common Name English
TETRABENAZINE [VANDF]
Common Name English
TETRABENAZINE [MI]
Common Name English
RO 1-9569
Code English
TETRABENAZINE [MART.]
Common Name English
TETRABENAZINE [USP-RS]
Common Name English
NSC-169886
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 108897
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
FDA ORPHAN DRUG 109797
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
WHO-VATC QN07XX06
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
LIVERTOX NBK548187
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
NDF-RT N0000190856
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
NCI_THESAURUS C471
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
FDA ORPHAN DRUG 278109
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
WHO-ATC N07XX06
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
Code System Code Type Description
MESH
D013747
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
MERCK INDEX
m10596
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY Merck Index
CAS
58-46-8
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
DRUG CENTRAL
2609
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
RXCUI
10390
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY RxNorm
NSC
169886
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
NCI_THESAURUS
C81095
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
DRUG BANK
DB04844
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
SMS_ID
100000092314
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
IUPHAR
4834
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
DAILYMED
Z9O08YRN8O
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
CHEBI
9467
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
EVMPD
SUB10939MIG
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-383-6
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL117785
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
WIKIPEDIA
TETRABENAZINE
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
RS_ITEM_NUM
1649801
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID0042614
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
INN
1056
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
NDF-RT
N0000190855
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY Vesicular Monoamine Transporter 2 Inhibitors [MoA]
FDA UNII
Z9O08YRN8O
Created by admin on Mon Mar 31 18:43:38 GMT 2025 , Edited by admin on Mon Mar 31 18:43:38 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET -> INHIBITOR
IC50
EXCRETED UNCHANGED
Unchanged tetrabenazine has not been found in human urine.
URINE
SALT/SOLVATE -> PARENT
OFF TARGET->NON-INHIBITOR
IC50
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
MINOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY