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Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO3.CH4O3S
Molecular Weight 413.528
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRABENAZINE METHANESULFONATE

SMILES

CS(O)(=O)=O.[H][C@@]12CC(=O)[C@@H](CC(C)C)CN1CCC3=CC(OC)=C(OC)C=C23

InChI

InChIKey=RHDADYXNUCMTQG-DMLYUBSXSA-N
InChI=1S/C19H27NO3.CH4O3S/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;1-5(2,3)4/h8-9,12,14,16H,5-7,10-11H2,1-4H3;1H3,(H,2,3,4)/t14-,16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.21875844E12
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

1.21875844E12
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

1.21875844E12
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
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
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 (starting)
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
Condition: Huntington’s disease
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
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Confusion
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Crisis oculogyric
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Diarrhea
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Hallucinations
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Hypotension
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Nausea and vomiting
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Redness
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Sedation
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Sweating
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Tremor
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unknown, adult
n = 8
Health Status: unknown
Age Group: adult
Population Size: 8
Sources:
Depression
12.5 mg 1 times / day steady, oral (starting)
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
Condition: Huntington’s disease
Age Group: adult
Sources:
Suicidal tendency
12.5 mg 1 times / day steady, oral (starting)
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
Condition: Huntington’s disease
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
Pharmacological analysis of a new anorexic substance: 5-hydroxy-5(4'-chlorophenyl)-2, 3-dihydro-5H-imidazo-(2, 1-a) isoindole (Mazindol).
1975 Apr
Adenosine release in morphine-induced hypotension in rats.
1992 Jan
Pharmacological options for the treatment of Tourette's disorder.
2001
Dual-[11C]tracer single-acquisition positron emission tomography studies.
2001 Dec
Dyskinesia: L-dopa-induced and tardive dyskinesia.
2001 Nov-Dec
Assessing the integrity of the dopamine system in Parkinson's disease: how best to do it?
2001 Sep
Repetitive administration of tetrabenazine induces irreversible changes in locomotion and morphology of the substantia nigra in rats.
2001 Sep
Characterization of high-affinity [3H]TBZOH binding to the human platelet vesicular monoamine transporter.
2001 Sep 28
Hemiballismus.
2002 Apr
Increased platelet vesicular monoamine transporter density in adult schizophrenia patients.
2002 Aug
[Herpetic encephalitis in childhood: a diagnosis which should not be forgotten].
2002 Feb 16-28
Antidepressant effects of the methanol extract of several Hypericum species from the Canary Islands.
2002 Jan
Tetrabenazine fails to antagonize a behavioral effect of cocaine in rhesus monkeys.
2002 Jan-Feb
Experimental conditions for the continuous subcutaneous infusion of four central analgesics in rats.
2002 Jul
Human megakaryocytes cultured in vitro accumulate serotonin but not meta-iodobenzylguanidine whereas platelets concentrate both.
2002 Jun
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
Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity.
2002 Mar
In vivo measures of dopaminergic radioligands in the rat brain: equilibrium infusion studies.
2002 Mar 1
Norepinephrine triggers Ca2+-dependent exocytosis of 5-hydroxytryptamine from rat pinealocytes in culture.
2002 May
Tetrabenazine treatment for Huntington's disease-associated chorea.
2002 Nov-Dec
Methylphenidate redistributes vesicular monoamine transporter-2: role of dopamine receptors.
2002 Oct 1
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
Non-synaptic release of [3H]noradrenaline in response to oxidative stress combined with mitochondrial dysfunction in rat hippocampal slices.
2003
Psychopharmacological effects of tianeptine analogous hetero[2,1] benzothiazepine derivatives.
2003
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
Obstructive sleep apnea is related to a thalamic cholinergic deficit in MSA.
2003 Jul 8
Effects of adrenal medulla graft on recovery of GABAergic and dopaminergic neuron deficits in mice: behavioural, pharmacological and immunohistochemical study.
2003 Mar 18
Decreased limbic vesicular monoamine transporter 2 in a genetic rat model of depression.
2003 Mar 7
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
Dopamine transmission in DYT1 dystonia.
2004
[Movement disorders in childhood: therapeutic update].
2004 Aug
Differential effects of scopolamine on in vivo binding of dopamine transporter and vesicular monoamine transporter radioligands in rat brain.
2004 Aug
Long-term reproducibility of in vivo measures of specific binding of radioligands in rat brain.
2004 Jul
Identification of tissue-restricted transcripts in human islets.
2004 Oct
Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters.
2004 Sep
The role of radiotracer imaging in Parkinson disease.
2005 Jan 25
Decreased platelet vesicular monoamine transporter density in habitual smokers.
2005 Mar
Decreased platelet vesicular monoamine transporter density in children and adolescents with attention deficit/hyperactivity disorder.
2005 Mar
Antidepressant properties of some Hypericum canariense L. and Hypericum glandulosum Ait. extracts in the forced swimming test in mice.
2005 Mar 21
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects.
2005 Nov
Pharmacological management of Huntington's disease: an evidence-based review.
2006
Tetrabenazine as antichorea therapy in Huntington disease: a randomized controlled trial.
2006 Feb 14
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
A blessing in disguise: resolution of tardive dyskinesia with development of cervical myelitis.
2006 Jan
Tetrabenazine versus placebo for chorea in Huntington's disease.
2006 Jul
Preparation and evaluation of tetrabenazine enantiomers and all eight stereoisomers of dihydrotetrabenazine as VMAT2 inhibitors.
2011 May
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 Fri Dec 15 19:10:00 UTC 2023
Edited
by admin
on Fri Dec 15 19:10:00 UTC 2023
Record UNII
5X57I1N37U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRABENAZINE METHANESULFONATE
MI  
Common Name English
TETRABENAZINE MESYLATE
Common Name English
(3R,11BR)-REL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-2H-BENZO(A)QUINOLIZIN-2-ONE METHANESULFONATE
Common Name English
(3R,11BR)-REL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-2H-BENZO(A)QUINOLIZIN-2-ONE METHANESULPHONATE
Common Name English
TETRABENAZINE MESILATE
Common Name English
TETRABENAZINE METHANESULPHONATE
Common Name English
TETRABENAZINE METHANESULFONATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
Code System Code Type Description
MERCK INDEX
m10596
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY Merck Index
EVMPD
SUB16464MIG
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
PUBCHEM
71586770
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
FDA UNII
5X57I1N37U
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
CAS
804-53-5
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
SMS_ID
100000078589
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID20230302
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
NCI_THESAURUS
C97410
Created by admin on Fri Dec 15 19:10:00 UTC 2023 , Edited by admin on Fri Dec 15 19:10:00 UTC 2023
PRIMARY
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