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
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21396745https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021894lbl.pdfCurator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21396745https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021894lbl.pdf
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21396745 |
36.4 µM [Ki] | ||
Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21396745 |
54.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | XENAZINE Approved UseTetrabenazine 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 Date2008 |
|||
| Primary | XENAZINE Approved UseTetrabenazine 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 Date2008 |
|||
| Primary | XENAZINE Approved UseTetrabenazine 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 Date2008 |
|||
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.66 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23339053 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.45 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23339053 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23339053 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
14% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23339053 |
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
| Dose | Population | Adverse events |
|---|---|---|
1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
Other AEs: Acute dystonia, Crisis oculogyric... Other AEs: Acute dystonia Sources: Crisis oculogyric Nausea and vomiting Sweating Sedation Hypotension Confusion Diarrhea Hallucinations Redness Tremor |
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... Other AEs: Depression Sources: Suicidal tendency |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Acute dystonia | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Confusion | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Crisis oculogyric | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Diarrhea | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Hallucinations | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Hypotension | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Nausea and vomiting | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Redness | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Sedation | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Sweating | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| Tremor | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: |
unknown, adult Health Status: unknown Age Group: adult Sources: |
|
| 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: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 67, 79 |
inconclusive | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 66, 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 67, 79 |
no | |||
Page: 80.0 |
no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 77.0 |
inconclusive | |||
Page: 76.0 |
inconclusive | |||
Page: 76.0 |
inconclusive | |||
Page: 80.0 |
no | no (co-administration study) Comment: tetrabenazine did not affect bioavailability of digoxin Page: 80.0 |
||
Page: 76.0 |
yes | |||
Page: 14, 65, 76 |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:43:38 GMT 2025
by
admin
on
Mon Mar 31 18:43:38 GMT 2025
|
| Record UNII |
Z9O08YRN8O
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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] | ||
|
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 |
|