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
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
Molecular Formula | C19H27NO3 |
Molecular Weight | 317.4233 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021894lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/21396745Curator'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.accessdata.fda.gov/drugsatfda_docs/label/2008/021894lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/21396745
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 is used to treat Huntington’s disease symptoms and other hyperkinetic movement disorders. It is sold as the racemate. Tetrabenazine (-) is 8000-fold less potent than Tetrabenazine (+) form in VMAT2 (target) binding assay.
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 Date1.21875844E12 |
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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 Date1.21875844E12 |
|||
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 Date1.21875844E12 |
|||
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 n = 8 Health Status: unknown Age Group: adult Population Size: 8 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 (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... 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 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: |
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 |
---|---|---|
[Behavior pharmacology of maprotiline, a new antidepressant]. | 1975 Nov |
|
Adenosine release in morphine-induced hypotension in rats. | 1992 Jan |
|
Elevated platelet vesicular monoamine transporter density in untreated patients diagnosed with major depression. | 2002 Nov 15 |
|
Tetrabenazine treatment for Huntington's disease-associated chorea. | 2002 Nov-Dec |
|
Catastrophic reactions induced by tetrabenazine. | 2002 Sep |
|
Non-synaptic release of [3H]noradrenaline in response to oxidative stress combined with mitochondrial dysfunction in rat hippocampal slices. | 2003 |
|
Increased ventral striatal monoaminergic innervation in Tourette syndrome. | 2003 Aug 12 |
|
Raclopride studies of dopamine release: dependence on presynaptic integrity. | 2003 Dec 1 |
|
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 |
|
Successful therapy of tardive dyskinesia in a 71-year-old woman with a combination of tetrabenazine, olanzapine and tiapride. | 2003 Mar |
|
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 |
|
Assessment of neuroimaging techniques as biomarkers of the progression of Parkinson's disease. | 2003 Nov |
|
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 |
|
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 |
|
Adrafinil-induced orofacial dyskinesia. | 2004 Aug |
|
[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 |
|
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 |
|
Behavioral and neurochemical consequences of long-term intravenous self-administration of MDMA and its enantiomers by rhesus monkeys. | 2004 Jul |
|
Striatal monoamine terminals in Lewy body dementia and Alzheimer's disease. | 2004 Jun |
|
Identification of tissue-restricted transcripts in human islets. | 2004 Oct |
|
The effect of rare human sequence variants on the function of vesicular monoamine transporter 2. | 2004 Sep |
|
Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. | 2004 Sep |
|
Tetrabenazine treatment in movement disorders. | 2004 Sep-Oct |
|
PET in LRRK2 mutations: comparison to sporadic Parkinson's disease and evidence for presymptomatic compensation. | 2005 Dec |
|
The role of radiotracer imaging in Parkinson disease. | 2005 Jan 25 |
|
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 habitual smokers. | 2005 Mar |
|
Emerging drugs in Tourette syndrome. | 2005 May |
|
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. | 2005 Nov |
|
Platelet vesicular monoamine transporter density in untreated patients diagnosed with social phobia. | 2005 Sep 15 |
|
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 |
|
Measurement of kinetically resolved vesicular dopamine uptake and efflux using rotating disk electrode voltammetry. | 2006 Jul 15 |
|
Longitudinal noninvasive PET-based beta cell mass estimates in a spontaneous diabetes rat model. | 2006 Jun |
|
Huntington's Disease. | 2006 May |
|
Interaction of amphetamines and related compounds at the vesicular monoamine transporter. | 2006 Oct |
|
Positron emission tomography of monoaminergic vesicular binding in aging and Parkinson disease. | 2006 Sep |
Sample Use Guides
The dose of XENAZINE should be individualized. The starting dose should be 12.5 mg per day given once in the morning. After one week, the dose should be increased to 25 mg per day given as 12.5 mg twice a day.
XENAZINE should be titrated up slowly at weekly intervals by 12.5 mg, to allow the identification of a dose that reduces chorea and is well tolerated. If a dose of 37.5 to 50 mg per day is needed, it should be given in a
three times a day regimen. The maximum recommended single dose is 25 mg. If adverse events such as akathisia, restlessness, parkinsonism, depression, insomnia, anxiety or intolerable sedation occur, titration should
be stopped and the dose should be reduced. If the adverse event does not resolve, consideration should be given to withdrawing XENAZINE treatment or initiating other specific treatment (e.g., antidepressants).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21396745
The brains from male SpragueeDawley rats (approximately 200-225 g weight) (Taconic Labs) were removed, placed on ice, and the striatum was rapidly removed and frozen (-80 C). Thereafter, membranes were prepared by homogenizing striatum samples in 20 volumes (w/v) of ice cold HEPES-sucrose buffer (50 mM HEPES, 0.32 M sucrose, pH adjusted to 8.0) using a Brinkman Polytron (setting 6 for 20 s), and centrifuging them at 20,000xg for 10 min at 4 C. The resulting pellet was resuspended in buffer, recentrifuged and again resuspended in buffer to provide a concentration of 10 mg/mL. Ligand binding experiments were conducted in polystyrene assay tubes containing 0.5 mL HEPES-sucrose buffer for 60 min at room temperature. Each tube contained 2 nM [3H]DHTBZ (specific activity 20 Ci/mmol) (American Radiolabeled Chemicals) and 1.0 mg striatal tissue (original wet weight). Nonspecific binding was determined using 20 mkM(+/-)-TBZ (Tetrabenazine) (Sigma Chemical Co., St Louis, MO). Incubations were terminated by rapid filtration through Whatman GF/B filters, presoaked in 0.5% PEI (polyethyleneimine), using a Brandel R48 filtering manifold (Brandel Instruments Gaithersburg, MD). These filters were then washed twice with 5 mL cold buffer and placed in scintillation vials. Beckman Ready Safe (3.0 mL) was added and the vials were counted the next day using
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 08:08:36 UTC 2021
by
admin
on
Sat Jun 26 08:08:36 UTC 2021
|
Record UNII |
Z9O08YRN8O
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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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
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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
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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
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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
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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
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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
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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
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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
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Code System | Code | Type | Description | ||
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D013747
Created by
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PRIMARY | |||
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M10596
Created by
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PRIMARY | Merck Index | ||
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58-46-8
Created by
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PRIMARY | |||
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2609
Created by
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PRIMARY | |||
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10390
Created by
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PRIMARY | RxNorm | ||
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C81095
Created by
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PRIMARY | |||
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DB04844
Created by
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PRIMARY | |||
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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
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PRIMARY | |||
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SUB10939MIG
Created by
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PRIMARY | |||
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200-383-6
Created by
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PRIMARY | |||
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CHEMBL117785
Created by
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PRIMARY | |||
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TETRABENAZINE
Created by
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PRIMARY | |||
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1649801
Created by
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PRIMARY | USP-RS | ||
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58-46-8
Created by
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PRIMARY | |||
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1056
Created by
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PRIMARY | |||
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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
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PRIMARY | Vesicular Monoamine Transporter 2 Inhibitors [MoA] | ||
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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
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PRIMARY |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> INHIBITOR | |||
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EXCRETED UNCHANGED |
Unchanged tetrabenazine has not been found in human urine.
URINE
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |