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

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

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
[Behavior pharmacology of maprotiline, a new antidepressant].
1975 Nov
Adenosine release in morphine-induced hypotension in rats.
1992 Jan
Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells.
1999 Jun 1
Pharmacological options for the treatment of Tourette's disorder.
2001
Interactions of 1-methyl-4-phenylpyridinium and other compounds with P-glycoprotein: relevance to toxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.
2001 Aug 10
Hemichorea, moya-moya, and ulcerative colitis.
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
Assessing the integrity of the dopamine system in Parkinson's disease: how best to do it?
2001 Sep
Hemiballismus.
2002 Apr
Increased platelet vesicular monoamine transporter density in adult schizophrenia patients.
2002 Aug
Evaluation of the central properties of several Hypericum species from the Canary Islands.
2002 Dec
Human megakaryocytes cultured in vitro accumulate serotonin but not meta-iodobenzylguanidine whereas platelets concentrate both.
2002 Jun
Chronic clozapine, but not haloperidol, treatment affects rat brain vesicular monoamine transporter 2.
2002 Jun
Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity.
2002 Mar
Elevated platelet vesicular monoamine transporter density in untreated patients diagnosed with major depression.
2002 Nov 15
Methylphenidate redistributes vesicular monoamine transporter-2: role of dopamine receptors.
2002 Oct 1
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
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
Increased ventral striatal monoaminergic innervation in Tourette syndrome.
2003 Aug 12
Self-biting induced by activation of L-type calcium channels in mice: dopaminergic influences.
2003 Jan-Feb
Obstructive sleep apnea is related to a thalamic cholinergic deficit in MSA.
2003 Jul 8
REM sleep behavior disorder is related to striatal monoaminergic deficit in MSA.
2003 Jul 8
Gilles de la Tourette's syndrome.
2003 Mar
Decreased limbic vesicular monoamine transporter 2 in a genetic rat model of depression.
2003 Mar 7
Dopamine transmission in DYT1 dystonia.
2004
Adrafinil-induced orofacial dyskinesia.
2004 Aug
[Movement disorders in childhood: therapeutic update].
2004 Aug
Electrochemical monitoring of transport by a vesicular monoamine transporter expressed in Xenopus oocytes.
2004 Feb 15
Behavioral and neurochemical consequences of long-term intravenous self-administration of MDMA and its enantiomers by rhesus monkeys.
2004 Jul
Identification of tissue-restricted transcripts in human islets.
2004 Oct
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
Decreased platelet vesicular monoamine transporter density in children and adolescents with attention deficit/hyperactivity disorder.
2005 Mar
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 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
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 Sat Dec 17 02:06:18 UTC 2022
Edited
by admin
on Sat Dec 17 02:06:18 UTC 2022
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 Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
Code System Code Type Description
MERCK INDEX
M10596
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY Merck Index
EVMPD
SUB16464MIG
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY
PUBCHEM
71586770
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY
EPA CompTox
DTXSID20230302
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY
FDA UNII
5X57I1N37U
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY
CAS
804-53-5
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY
NCI_THESAURUS
C97410
Created by admin on Sat Dec 17 02:06:18 UTC 2022 , Edited by admin on Sat Dec 17 02:06:18 UTC 2022
PRIMARY
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