Deutetrabenazine

Identification

Summary

Deutetrabenazine is a vesicular monoamine transporter 2 inhibitor used for the symptomatic treatment of tardive dyskinesia and chorea associated with Huntington's disease.

Brand Names

Austedo

Generic Name

Deutetrabenazine

DrugBank Accession Number

DB12161

Background

Deutetrabenazine is a novel, highly selective vesicular monoamine transporter 2 (VMAT2) inhibitor indicated for the management of chorea associated with Huntington’s disease. It is a hexahydro-dimethoxybenzoquinolizine derivative and a deuterated Tetrabenazine ⁵. The presence of deuterium in deutetrabenazine increases the half-lives of the active metabolite and prolongs their pharmacological activity by attenuating CYP2D6 metabolism of the compound ⁵. This allows less frequent dosing and a lower daily dose with improvement in tolerability ². Decreased plasma fluctuations of deutetrabenazine due to attenuated metabolism may explain a lower incidence of adverse reactions associated with deutetrabenazine ¹. Deutetrabenazine is a racemic mixture containing RR-Deutetrabenazine and SS-Deutetrabenazine ^Label.

Huntington's disease (HD) is a hereditary, progressive neurodegenerative disorder characterized by motor dysfunction, cognitive decline, and neuropsychiatric disturbances ² that interfere with daily functioning and significantly reduce the quality of life. The most prominent physical symptom of HD that may increase the risk of injury is chorea, which is an involuntary, sudden movement that can affect any muscle and flow randomly across body regions ⁵. Psychomotor symptoms of HD, such as chorea, are related to hyperactive dopaminergic neurotransmission ⁶. Deutetrabenazine depletes the levels of presynaptic dopamine by blocking VMAT2, which is responsible for the uptake of dopamine into synaptic vesicles in monoaminergic neurons and exocytotic release ⁶. As with other agents for the treatment of neurodegenerative diseases, deutetrabenazine is a drug to alleviate the motor symptoms of HD and is not proposed to halt the progression of the disease ⁷. In clinical trials of patients with HD, 12 weeks of treatment of deutetrabenazine resulted in overall improvement in mean total maximal chorea scores and motor signs than placebo ⁵. It was approved by FDA in April 2017 and is marketed under the trade name Austedo as oral tablets.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Deutetrabenazine (DB12161)

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Weight

Average: 323.466
Monoisotopic: 323.236754209

Chemical Formula

C₁₉H₂₇NO₃

Synonyms

• D6 tetrabenazine
• D6-tetrabenazine
• Deutetrabenazine
• Tetrabenazine D6
• Tetrabenazine-D6

External IDs

• SD-809

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Pharmacology

Indication

Deutetrabenazine is indicated in adults patients for the treatment of tardive dyskinesia and for chorea associated with Huntington's disease.⁸

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Chorea		••••••••••••	•••••		••••••
Management of	Tardive dyskinesia (td)		••••••••••••	•••••		••••••

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Pharmacodynamics

In clinical trials, there was an evidence of clinical effectiveness of deutetrabenazine in improving the symptoms of involuntary movements in patient with tardive dyskinesia by reducing the mean Abnormal Involuntary Movement Scale (AIMS) score ^3,4. In a randomized, double-blind, placebo-controlled crossover study in healthy male and female subjects, single dose administration of 24 mg deutetrabenazine results in an approximately 4.5 msec mean increase in QTc ^Label. Effects at higher exposures to deutetrabenazine or its metabolites have not been evaluated ^Label. Deutetrabenazine and its metabolites were shown to bind to melanin-containing tissues including eyes, skin and fur in pigmented rats. After a single oral dose of radiolabeled deutetrabenazine, radioactivity was still detected in eye and fur at 35 days following dosing ^Label.

Mechanism of action

The precise mechanism of action of deutetrabenazine in mediating its anti-chorea effects is not fully elucidated. Deutetrabenazine reversibly depletes the levels of monoamines, such as dopamine, serotonin, norepinephrine, and histamine, from nerve terminals via its active metabolites. The major circulating metabolites are α-dihydrotetrabenazine [HTBZ] and β-HTBZ that act as reversible inhibitors of VMAT2. Inhibition of VMAT2 results in decreased uptake of monoamines into synaptic terminal and depletion of monoamine stores from nerve terminals ^Label.

Deutetrabenazine contains the molecule deuterium, which is a naturally-occurring, nontoxic hydrogen isotope but with an increased mass relative to hydrogen ⁵. Placed at key positions, deuterium forms a stronger hydrogen bond with carbon that requires more energy for cleavage, thus attenuating CYP2D6-mediated metabolism without having any effect on the therapeutic target ⁵.

Target	Actions	Organism
ASynaptic vesicular amine transporter	inhibitor	Humans

Absorption

The extent of absorption is 80% with oral deutetrabenazine. As deutetrabenazine is extensively metabolized to its main active metabolites following administration, linear dose dependence of peak plasma concentrations (Cmax) and AUC was observed for the metabolites after single or multiple doses of deutetrabenazine (6 mg to 24 mg and 7.5 mg twice daily to 22.5 mg twice daily) ^Label. Cmax of deuterated α-HTBZ and β-HTBZ are reached within 3-4 hours post-dosing ^Label. Food may increase the Cmax of α-HTBZ or β-HTBZ by approximately 50%, but is unlikely to have an effect on the AUC ^Label.

Volume of distribution

The median volume of distribution (Vc/F) of the α-HTBZ, and the β-HTBZ metabolites of deutetrabenazine are approximately 500 L and 730 L, respectively ^Label. Human PET-scans of tetrabenazine indicate rapid distribution to the brain, with the highest binding in the striatum and lowest binding in the cortex ^Label. Similar distribution pattern is expected for deutetrabenazine.

Protein binding

At doses ranging from 50 to 200 ng/mL in vitro, tetrabenazine protein binding ranged from 82% to 85%, α-HTBZ binding ranged from 60% to 68%, and β-HTBZ binding ranged from 59% to 63% ^Label. Similar protein binding pattern is expected for deutetrabenazine and its metabolites.

Metabolism

Deutetrabenazine undergoes extensive hepatic biotransformation mediated by carbonyl reductase to form its major active metabolites, α-HTBZ and β­-HTBZ. These metabolites may subsequently metabolized to form several minor metabolites, with major contribution of CYP2D6 and minor contributions of CYP1A2 and CYP3A4/5 ^Label.

Route of elimination

Deutetrabenazine is mainly excreted in the urine as metabolites. In healthy subjects, about 75% to 86% of the deutetrabenazine dose was excreted in the urine, and fecal recovery accounted for 8% to 11% of the dose ^Label. Sulfate and glucuronide conjugates of the α-HTBZ and β-HTBZ, as well as products of oxidative metabolism, accounted for the majority of metabolites in the urine ^Label. α-HTBZ and β-HTBZ metabolites accounted for less than 10% of the administered dose in the urine ^Label.

Half-life

The half-life of total (α+β)-HTBZ from deutetrabenazine is approximately 9 to 10 hours ^Label.

Clearance

In patients with Huntington's disease, the median clearance values (CL/F) of the α-HTBZ, and the β-HTBZ metabolites of deutetrabenazine are approximately 47 L/hour and 70 L/hour, respectively ^Label.

Adverse Effects

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Toxicity

Adverse reactions associated with overdosage include acute dystonia, oculogyric crisis, nausea and vomiting, sweating, sedation, hypotension, confusion, diarrhea, hallucinations, rubor, and tremor ^Label. In case of an overdose, general supportive and symptomatic measures are recommended while monitoring cardiac rhythm and vital signs. In managing overdosage, the possibility of multiple drug involvement should always be considered ^Label.

No carcinogenicity studies were performed with deutetrabenazine. In p53+/– transgenic mice, there were no detectable tumors following oral administration of deutetrabenazine at doses of 0, 5, 15, and 30 mg/kg/day for 26 weeks ^Label. Findings from in vitro assays and in vivo mice micronucleus assay suggest that deutetrabenazine and its metabolites are unlikely to be mutagenic ^Label. The effects of deutetrabenazine on fertility have not been evaluated. Oral administration of tetrabenazine had no effects on mating and reproductive systems of male and female rats ^Label.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Deutetrabenazine which could result in a higher serum level.
Abametapir	The serum concentration of Deutetrabenazine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Deutetrabenazine can be increased when combined with Abatacept.
Abiraterone	The metabolism of Deutetrabenazine can be decreased when combined with Abiraterone.
Acalabrutinib	The metabolism of Deutetrabenazine can be decreased when combined with Acalabrutinib.

Food Interactions

• Avoid alcohol. Additive sedative effects may occur from co-administration of deutetrabenazine with alcohol.
• Take with food. Taking deutetrabenazine with food increases its Cmax.

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Austedo	Tablet, coated	12 mg/1	Oral	Teva Neuroscience, Inc.	2017-04-12	Not applicable
Austedo	Tablet, coated	9 mg/1	Oral	Teva Neuroscience, Inc.	2017-04-12	Not applicable
Austedo	Kit; Tablet	6 mg/1	Oral	Teva Neuroscience, Inc.	2020-02-01	2023-02-28
Austedo	Tablet, coated	6 mg/1	Oral	Teva Neuroscience, Inc.	2017-04-12	Not applicable
Austedo XR	Tablet, film coated, extended release	12 mg/1	Oral	Teva Neuroscience, Inc.	2023-02-21	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Austedo	Deutetrabenazine (6 mg/1) + Deutetrabenazine (9 mg/1) + Deutetrabenazine (12 mg/1)	Kit; Tablet, coated	Oral	Teva Neuroscience, Inc.	2021-05-06	2024-02-29
Austedo	Deutetrabenazine (6 mg/1) + Deutetrabenazine (9 mg/1) + Deutetrabenazine (12 mg/1)	Kit; Tablet, coated	Oral	Teva Neuroscience, Inc.	2021-05-06	2023-02-28
Austedo	Deutetrabenazine (6 mg/1) + Deutetrabenazine (9 mg/1) + Deutetrabenazine (12 mg/1)	Kit; Tablet, coated	Oral	Teva Neuroscience, Inc.	2021-05-06	2024-02-29
Austedo	Deutetrabenazine (6 mg/1) + Deutetrabenazine (9 mg/1) + Deutetrabenazine (12 mg/1)	Kit; Tablet, coated	Oral	Teva Neuroscience, Inc.	2021-05-06	2023-02-28
Austedo	Deutetrabenazine (6 mg/1) + Deutetrabenazine (9 mg/1)	Kit; Tablet	Oral	Teva Neuroscience, Inc.	2020-02-01	Not applicable

Categories

ATC Codes

N07XX16 — Deutetrabenazine

• N07XX — Other nervous system drugs
• N07X — OTHER NERVOUS SYSTEM DRUGS
• N07 — OTHER NERVOUS SYSTEM DRUGS
• N — NERVOUS SYSTEM

Drug Categories

• Cytochrome P-450 CYP1A2 Substrates
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• Heterocyclic Compounds, Fused-Ring
• Highest Risk QTc-Prolonging Agents
• Nervous System
• QTc Prolonging Agents
• Quinolizines
• Vesicular Monoamine Transporter 2 Inhibitor
• Vesicular Monoamine Transporter 2 Inhibitors

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Anisoles / Piperidinones / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Cyclic ketones / Azacyclic compounds / Organic oxides / Hydrocarbon derivatives

Substituents

Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Cyclic ketone / Ether

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

P341G6W9NB

CAS number

1392826-25-3

InChI Key

MKJIEFSOBYUXJB-WEZHFFAMSA-N

InChI

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/i3D3,4D3

IUPAC Name

(3S,11bS)-9,10-di(2H3)methoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

SMILES

[2H]C([2H])([2H])OC1=CC2=C(C=C1OC([2H])([2H])[2H])[C@@H]1CC(=O)[C@@H](CC(C)C)CN1CC2

References

General References

1. Paton DM: Deutetrabenazine: Treatment of hyperkinetic aspects of Huntington's disease, tardive dyskinesia and Tourette syndrome. Drugs Today (Barc). 2017 Feb;53(2):89-102. doi: 10.1358/dot.2017.53.2.2589164. [Article]
2. Rodrigues FB, Duarte GS, Costa J, Ferreira JJ, Wild EJ: Tetrabenazine Versus Deutetrabenazine for Huntington's Disease: Twins or Distant Cousins? Mov Disord Clin Pract. 2017 Jul-Aug;4(4):582-585. doi: 10.1002/mdc3.12483. Epub 2017 Mar 29. [Article]
3. Anderson KE, Stamler D, Davis MD, Factor SA, Hauser RA, Isojarvi J, Jarskog LF, Jimenez-Shahed J, Kumar R, McEvoy JP, Ochudlo S, Ondo WG, Fernandez HH: Deutetrabenazine for treatment of involuntary movements in patients with tardive dyskinesia (AIM-TD): a double-blind, randomised, placebo-controlled, phase 3 trial. Lancet Psychiatry. 2017 Aug;4(8):595-604. doi: 10.1016/S2215-0366(17)30236-5. Epub 2017 Jun 28. [Article]
4. Fernandez HH, Factor SA, Hauser RA, Jimenez-Shahed J, Ondo WG, Jarskog LF, Meltzer HY, Woods SW, Bega D, LeDoux MS, Shprecher DR, Davis C, Davis MD, Stamler D, Anderson KE: Randomized controlled trial of deutetrabenazine for tardive dyskinesia: The ARM-TD study. Neurology. 2017 May 23;88(21):2003-2010. doi: 10.1212/WNL.0000000000003960. Epub 2017 Apr 26. [Article]
5. Frank S, Testa CM, Stamler D, Kayson E, Davis C, Edmondson MC, Kinel S, Leavitt B, Oakes D, O'Neill C, Vaughan C, Goldstein J, Herzog M, Snively V, Whaley J, Wong C, Suter G, Jankovic J, Jimenez-Shahed J, Hunter C, Claassen DO, Roman OC, Sung V, Smith J, Janicki S, Clouse R, Saint-Hilaire M, Hohler A, Turpin D, James RC, Rodriguez R, Rizer K, Anderson KE, Heller H, Carlson A, Criswell S, Racette BA, Revilla FJ, Nucifora F Jr, Margolis RL, Ong M, Mendis T, Mendis N, Singer C, Quesada M, Paulsen JS, Brashers-Krug T, Miller A, Kerr J, Dubinsky RM, Gray C, Factor SA, Sperin E, Molho E, Eglow M, Evans S, Kumar R, Reeves C, Samii A, Chouinard S, Beland M, Scott BL, Hickey PT, Esmail S, Fung WL, Gibbons C, Qi L, Colcher A, Hackmyer C, McGarry A, Klos K, Gudesblatt M, Fafard L, Graffitti L, Schneider DP, Dhall R, Wojcieszek JM, LaFaver K, Duker A, Neefus E, Wilson-Perez H, Shprecher D, Wall P, Blindauer KA, Wheeler L, Boyd JT, Houston E, Farbman ES, Agarwal P, Eberly SW, Watts A, Tariot PN, Feigin A, Evans S, Beck C, Orme C, Edicola J, Christopher E: Effect of Deutetrabenazine on Chorea Among Patients With Huntington Disease: A Randomized Clinical Trial. JAMA. 2016 Jul 5;316(1):40-50. doi: 10.1001/jama.2016.8655. [Article]
6. Wimalasena K: Vesicular monoamine transporters: structure-function, pharmacology, and medicinal chemistry. Med Res Rev. 2011 Jul;31(4):483-519. doi: 10.1002/med.20187. Epub 2010 Feb 4. [Article]
7. 39. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 489-490). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
8. FDA Approved Drug Products: Austedo (deutetrabenazine) tablets for oral use [Link]

External Links

PubChem Compound

73442840

PubChem Substance

347828453

ChemSpider

32700662

RxNav

1876905

Wikipedia

Deutetrabenazine

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Treatment	Chorea	1
3	Completed	Treatment	Coronavirus Disease 2019 (COVID‑19) / Dyskinetic Cerebral Palsy	1
3	Completed	Treatment	Gilles de la Tourette's Syndrome	1
3	Completed	Treatment	Huntington's Disease (HD)	1
3	Completed	Treatment	Tardive Dyskinesia (TD)	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Kit; tablet	Oral
Kit; tablet	Oral	6 mg/1
Kit; tablet, coated	Oral
Tablet, coated	Oral	12 mg/1
Tablet, coated	Oral	6 mg/1
Tablet, coated	Oral	9 mg/1
Kit; tablet, film coated, extended release	Oral
Tablet, film coated, extended release	Oral	12 mg/1
Tablet, film coated, extended release	Oral	24 mg/1
Tablet, film coated, extended release	Oral	6 mg/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8524733	Yes	2013-09-03	2031-09-27
US9296739	Yes	2016-03-29	2034-03-18
US9233959	Yes	2016-01-12	2034-03-18
US9550780	Yes	2017-01-24	2034-03-18
US9814708	Yes	2017-11-14	2034-03-18
US10959996	Yes	2021-03-30	2036-09-07
US11179386	Yes	2021-11-23	2038-09-15
US11357772	Yes	2016-09-07	2036-09-07
US11446291	Yes	2016-09-07	2036-09-07
US11564917	Yes	2016-09-07	2036-09-07
US11311488	No	2021-06-10	2041-06-10
US11648244	Yes	2016-09-07	2036-09-07
US11666566	Yes	2014-03-18	2034-03-18
US11813232	Yes	2018-09-15	2038-09-15

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.361 mg/mL	ALOGPS
logP	3.23	ALOGPS
logP	3.4	Chemaxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.26	Chemaxon
pKa (Strongest Basic)	7.33	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	38.77 Å2	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	91.31 m3·mol-1	Chemaxon
Polarizability	36.83 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0009000000-ba78836c58b00ab4e6c4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0009000000-f189fc658abb8f999018
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0049000000-e25754af93da67965901
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0139000000-13d752e602ef6e4c3252
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01p9-2390000000-c94ee9cdbabd19c82d12
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0w29-0390000000-12b1bea577b46f85cc04
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	189.45454	predicted	DeepCCS 1.0 (2019)
[M+H]+	191.34996	predicted	DeepCCS 1.0 (2019)
[M+Na]+	197.1279	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Synaptic vesicular amine transporter

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Monoamine transmembrane transporter activity

Specific Function

Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...

Gene Name

SLC18A2

Uniprot ID

Q05940

Uniprot Name

Synaptic vesicular amine transporter

Molecular Weight

55712.075 Da

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Drug created at October 20, 2016 21:30 / Updated at July 18, 2023 22:57