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Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO3
Molecular Weight 317.4233
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRABENAZINE

SMILES

CC(C)C[C@@]1([H])CN2CCc3cc(c(cc3[C@]2([H])CC1=O)OC)OC

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
Curator's Comment:: 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

TargetsConditions

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

1218758400000
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

1218758400000
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

1218758400000
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
[Behavior pharmacology of maprotiline, a new antidepressant].
1975 Nov
Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells.
1999 Jun 1
Reversal of tetrabenazine induced depression by selective noradrenaline (norepinephrine) reuptake inhibition.
1999 Oct
Meige syndrome secondary to basal ganglia injury: a potential cause of acute respiratory distress.
2001 May
Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain.
2001 May
Dyskinesia: L-dopa-induced and tardive dyskinesia.
2001 Nov-Dec
Repetitive administration of tetrabenazine induces irreversible changes in locomotion and morphology of the substantia nigra in rats.
2001 Sep
Cocaine-induced increases in vesicular dopamine uptake: role of dopamine receptors.
2001 Sep
Vesicular neurotransmitter transporters in Huntington's disease: initial observations and comparison with traditional synaptic markers.
2001 Sep 15
Elevated platelet vesicular monoamine transporter density in untreated patients diagnosed with major depression.
2002 Nov 15
Lack of effect of testosterone and dihydrotestosterone compared to 17beta-oestradiol in 1-methyl-4-phenyl-1,2,3,6, tetrahydropyridine-mice.
2002 Sep
1-(Benzofuran-2-yl)-2-(3,3,3-trifluoropropyl)aminopentane HCl, 3-F-BPAP, antagonizes the enhancer effect of (-)-BPAP in the shuttle box and leaves the effect of (-)-deprenyl unchanged.
2002 Sep 13
Psychopharmacological effects of tianeptine analogous hetero[2,1] benzothiazepine derivatives.
2003
Tetrabenazine in the treatment of severe pediatric chorea.
2003 Jun
Effects of adrenal medulla graft on recovery of GABAergic and dopaminergic neuron deficits in mice: behavioural, pharmacological and immunohistochemical study.
2003 Mar 18
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
Differential effects of scopolamine on in vivo binding of dopamine transporter and vesicular monoamine transporter radioligands in rat brain.
2004 Aug
Lack of regional selectivity during the progression of Parkinson disease: implications for pathogenesis.
2004 Dec
Electrochemical monitoring of transport by a vesicular monoamine transporter expressed in Xenopus oocytes.
2004 Feb 15
Long-term reproducibility of in vivo measures of specific binding of radioligands in rat brain.
2004 Jul
Tetrabenazine treatment in movement disorders.
2004 Sep-Oct
Antidepressant properties of some Hypericum canariense L. and Hypericum glandulosum Ait. extracts in the forced swimming test in mice.
2005 Mar 21
Interaction of amphetamines and related compounds at the vesicular monoamine transporter.
2006 Oct
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
TETRABENAZINE [USP-RS]
Common Name English
NSC-169886
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 108897
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
FDA ORPHAN DRUG 109797
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
WHO-VATC QN07XX06
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
LIVERTOX 945
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
NDF-RT N0000190856
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
NCI_THESAURUS C471
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
FDA ORPHAN DRUG 278109
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
WHO-ATC N07XX06
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
Code System Code Type Description
MESH
D013747
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY
MERCK INDEX
M10596
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY Merck Index
CAS
58-46-8
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
DRUG CENTRAL
2609
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
RXCUI
10390
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C81095
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY
DRUG BANK
DB04844
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
IUPHAR
4834
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
EVMPD
SUB10939MIG
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-383-6
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL117785
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
WIKIPEDIA
TETRABENAZINE
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY
USP_CATALOG
1649801
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY USP-RS
EPA CompTox
58-46-8
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
INN
1056
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY
NDF-RT
N0000190855
Created by admin on Sat Jun 26 08:08:38 UTC 2021 , Edited by admin on Sat Jun 26 08:08:38 UTC 2021
PRIMARY Vesicular Monoamine Transporter 2 Inhibitors [MoA]
FDA UNII
Z9O08YRN8O
Created by admin on Sat Jun 26 08:08:37 UTC 2021 , Edited by admin on Sat Jun 26 08:08:37 UTC 2021
PRIMARY