Details of the Drug

General Information of Drug (ID: DMYWQ0O)

Drug Name

Tetrabenazine

Synonyms

Nitoman; Rubigen; Tetrabenazina; Tetrabenazinum; Tetrabenzaine; Tetrabenzine; Xenazine; Tetra Benazin; Nitoman (TN); Ro 1-9569; Tetrabenazina [INN-Spanish]; Tetrabenazine (INN); Tetrabenazine [INN:BAN]; Tetrabenazinum [INN-Latin]; Xenazine (TN); Nitoman, Xenazine, Tetrabenazine; Ro 1-9569/12; 1,3,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo(a)quinolizin-2-one; 1,3,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one; 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-Benzo[a]quinolizin-2-one; 2-Oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine; 2-Oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11-beta-hexahydro-2H-benzoquinolizine; 2-Oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11.beta.-hexahydro-2H-benzoquinolizine; 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-(9CI); 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one; 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one

Indication

Disease Entry	ICD 11	Status	REF
Huntington disease	8A01.10	Approved	[1]
Hyperkinetic movement disorder	6B60.8	Approved	[1]
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Therapeutic Class

Nephropathic cystinosis therapy

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

317.4

Logarithm of the Partition Coefficient (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination: 0% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 7 hours [3]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 45.0043 micromolar/kg/day [4]
Vd: The volume of distribution (Vd) of drug is 385 L []

Chemical Identifiers

Formula: C19H27NO3
IUPAC Name: 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
Canonical SMILES: CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1=O)OC)OC
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
InChIKey: MKJIEFSOBYUXJB-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 6018
ChEBI ID: CHEBI:64028
CAS Number: 718635-93-9
DrugBank ID: DB04844
TTD ID: D09PJX
VARIDT ID: DR01035
INTEDE ID: DR1567
ACDINA ID: D00667

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Synaptic vesicle amine transporter (SLC18A2)	TTNZRI3	VMAT2_HUMAN	Blocker	[5]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Synaptic vesicular amine transporter (SLC18A2)	OTUOMMM6	VMAT2_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Huntington disease

ICD Disease Classification

8A01.10

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Synaptic vesicle amine transporter (SLC18A2)	DTT	SLC18A2	2.69E-02	-0.04	-0.11
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	7.30E-01	-1.91E-02	-1.41E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Tetrabenazine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Major	Additive hypertensive effects by the combination of Tetrabenazine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[8]
Ivosidenib	DM8S6T7	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Ivosidenib.	Acute myeloid leukaemia [2A60]	[9]
Midostaurin	DMI6E0R	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Midostaurin.	Acute myeloid leukaemia [2A60]	[10]
Arn-509	DMT81LZ	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Arn-509.	Acute myeloid leukaemia [2A60]	[11]
Gilteritinib	DMTI0ZO	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Gilteritinib.	Acute myeloid leukaemia [2A60]	[10]
Oliceridine	DM6MDCF	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Oliceridine.	Acute pain [MG31]	[10]
Ivabradine	DM0L594	Major	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Ivabradine.	Angina pectoris [BA40]	[11]
Dronedarone	DMA8FS5	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Dronedarone.	Angina pectoris [BA40]	[10]
Bedaquiline	DM3906J	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[12]
Levalbuterol	DM5YBO1	Moderate	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Levalbuterol.	Asthma [CA23]	[13]
Retigabine	DMGNYIH	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Retigabine.	Behcet disease [4A62]	[10]
Eribulin	DM1DX4Q	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Eribulin.	Breast cancer [2C60-2C6Y]	[10]
Bosutinib	DMTI8YE	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Bosutinib.	Breast cancer [2C60-2C6Y]	[10]
PF-04449913	DMSB068	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and PF-04449913.	Chronic myelomonocytic leukaemia [2A40]	[10]
Olodaterol	DM62B78	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Olodaterol.	Chronic obstructive pulmonary disease [CA22]	[14]
Vilanterol	DMF5EK1	Moderate	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Vilanterol.	Chronic obstructive pulmonary disease [CA22]	[13]
Indacaterol	DMQJHR7	Moderate	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Indacaterol.	Chronic obstructive pulmonary disease [CA22]	[14]
Pasireotide	DMHM7JS	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Pasireotide.	Cushing syndrome [5A70]	[10]
Osilodrostat	DMIJC9X	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Osilodrostat.	Cushing syndrome [5A70]	[10]
OPC-34712	DMHG57U	Major	Additive antidopaminergic effects by the combination of Tetrabenazine and OPC-34712.	Depression [6A70-6A7Z]	[15]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Tetrabenazine and Esketamine.	Depression [6A70-6A7Z]	[16]
Deutetrabenazine	DMUPFLI	Major	Additive antidopaminergic effects by the combination of Tetrabenazine and Deutetrabenazine.	Dystonic disorder [8A02]	[8]
Ingrezza	DMVPLNC	Moderate	Additive CNS depression effects by the combination of Tetrabenazine and Ingrezza.	Dystonic disorder [8A02]	[17]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Tetrabenazine caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[18]
Mirabegron	DMS1GYT	Moderate	Decreased metabolism of Tetrabenazine caused by Mirabegron mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[19]
Fostemsavir	DM50ILT	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Fostemsavir.	Human immunodeficiency virus disease [1C60-1C62]	[10]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Tetrabenazine caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[20]
Rilpivirine	DMJ0QOW	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Rilpivirine.	Human immunodeficiency virus disease [1C60-1C62]	[10]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Tetrabenazine caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[21]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Tetrabenazine caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[22]
ITI-007	DMUQ1DO	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and ITI-007.	Insomnia [7A00-7A0Z]	[15]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[11]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Decreased metabolism of Tetrabenazine caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[11]
Crizotinib	DM4F29C	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Crizotinib.	Lung cancer [2C25]	[23]
Ceritinib	DMB920Z	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Ceritinib.	Lung cancer [2C25]	[10]
Dacomitinib	DMOH8VY	Major	Decreased metabolism of Tetrabenazine caused by Dacomitinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[24]
Osimertinib	DMRJLAT	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Osimertinib.	Lung cancer [2C25]	[25]
Selpercatinib	DMZR15V	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Selpercatinib.	Lung cancer [2C25]	[11]
Lumefantrine	DM29GAD	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Lumefantrine.	Malaria [1F40-1F45]	[16]
Inotuzumab ozogamicin	DMAC130	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Inotuzumab ozogamicin.	Malignant haematopoietic neoplasm [2B33]	[10]
Vemurafenib	DM62UG5	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Vemurafenib.	Melanoma [2C30]	[10]
LGX818	DMNQXV8	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and LGX818.	Melanoma [2C30]	[10]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Tetrabenazine and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[26]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Tetrabenazine and Lasmiditan.	Migraine [8A80]	[27]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Tetrabenazine and Flibanserin.	Mood disorder [6A60-6E23]	[28]
Panobinostat	DM58WKG	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Panobinostat.	Multiple myeloma [2A83]	[29]
Siponimod	DM2R86O	Major	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Siponimod.	Multiple sclerosis [8A40]	[16]
Fingolimod	DM5JVAN	Major	Increased risk of ventricular arrhythmias by the combination of Tetrabenazine and Fingolimod.	Multiple sclerosis [8A40]	[10]
Romidepsin	DMT5GNL	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Romidepsin.	Mycosis fungoides [2B01]	[10]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Tetrabenazine caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[11]
Nilotinib	DM7HXWT	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Nilotinib.	Myeloproliferative neoplasm [2A20]	[10]
Rolapitant	DM8XP26	Moderate	Decreased metabolism of Tetrabenazine caused by Rolapitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[30]
Entrectinib	DMMPTLH	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Entrectinib.	Non-small cell lung cancer [2C25]	[16]
Lorcaserin	DMG6OYJ	Moderate	Increased risk of hyperprolactinemic effects by the combination of Tetrabenazine and Lorcaserin.	Obesity [5B80-5B81]	[31]
Lofexidine	DM1WXA6	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Lofexidine.	Opioid use disorder [6C43]	[10]
Rucaparib	DM9PVX8	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Rucaparib.	Ovarian cancer [2C73]	[10]
Triclabendazole	DMPWGBR	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Triclabendazole.	Parasitic worm infestation [1F90]	[10]
Safinamide	DM0YWJC	Major	Additive hypertensive effects by the combination of Tetrabenazine and Safinamide.	Parkinsonism [8A00]	[8]
Pimavanserin	DMR7IVC	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Pimavanserin.	Parkinsonism [8A00]	[10]
Macimorelin	DMQYJIR	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Macimorelin.	Pituitary gland disorder [5A60-5A61]	[32]
Lefamulin	DME6G97	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Lefamulin.	Pneumonia [CA40]	[33]
Degarelix	DM3O8QY	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Degarelix.	Prostate cancer [2C82]	[11]
ABIRATERONE	DM8V75C	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and ABIRATERONE.	Prostate cancer [2C82]	[11]
Enzalutamide	DMGL19D	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Enzalutamide.	Prostate cancer [2C82]	[11]
Relugolix	DMK7IWL	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Relugolix.	Prostate cancer [2C82]	[11]
Iloperidone	DM6AUFY	Major	Additive antidopaminergic effects by the combination of Tetrabenazine and Iloperidone.	Schizophrenia [6A20]	[15]
Amisulpride	DMSJVAM	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Amisulpride.	Schizophrenia [6A20]	[15]
Asenapine	DMSQZE2	Major	Additive antidopaminergic effects by the combination of Tetrabenazine and Asenapine.	Schizophrenia [6A20]	[15]
LEE011	DMMX75K	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and LEE011.	Solid tumour/cancer [2A00-2F9Z]	[10]
Vandetanib	DMRICNP	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Vandetanib.	Solid tumour/cancer [2A00-2F9Z]	[10]
Triptorelin	DMTK4LS	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Triptorelin.	Solid tumour/cancer [2A00-2F9Z]	[11]
Pitolisant	DM8RFNJ	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Pitolisant.	Somnolence [MG42]	[10]
Telavancin	DM58VQX	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Telavancin.	Staphylococcal/streptococcal disease [1B5Y]	[10]
Lenvatinib	DMB1IU4	Moderate	Increased risk of prolong QT interval by the combination of Tetrabenazine and Lenvatinib.	Thyroid cancer [2D10]	[10]
Cabozantinib	DMIYDT4	Major	Increased risk of prolong QT interval by the combination of Tetrabenazine and Cabozantinib.	Thyroid cancer [2D10]	[11]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium stearyl fumarate	E00545	23665634	lubricant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
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⏷ Show the Full List of 7 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tetrabenazine 25 mg tablet	25 mg	Oral Tablet	Oral
Tetrabenazine 12.5 mg tablet	12.5 mg	Oral Tablet	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4834).
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8.
6	Role of tetrabenazine for Huntington's disease-associated chorea. Ann Pharmacother. 2010 Jun;44(6):1080-9.
7	The effect of rare human sequence variants on the function of vesicular monoamine transporter 2. Pharmacogenetics. 2004 Sep;14(9):587-94. doi: 10.1097/00008571-200409000-00003.
8	Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
9	Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA.
10	Canadian Pharmacists Association.
11	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
12	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
13	Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ.
14	Bengtsson B, Fagerstrom PO "Extrapulmonary effects of terbutaline during prolonged administration." Clin Pharmacol Ther 31 (1982): 726-32. [PMID: 7042176]
15	Burke RE, Fahn S, Mayeux R, Weinberg H, Louis K, Willner JH "Neuroleptic malignant syndrome caused by dopamine-depleting drugs in a patient with Huntington disease." Neurology 31 (1981): 1022-5. [PMID: 6115336]
16	Cerner Multum, Inc. "Australian Product Information.".
17	Product Information. Ingrezza (valbenazine). Neurocrine Biosciences, Inc., San Diego, CA.
18	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
19	Product Information. Myrbetriq (mirabegron). Astellas Pharma US, Inc, Deerfield, IL.
20	Product Information. Stribild (cobicistat/elvitegravir/emtricitabine/tenofov). Gilead Sciences, Foster City, CA.
21	Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
22	Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
23	Product Information. Xalkori (crizotinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
24	Product Information. Xenazine (tetrabenazine). Prestwick Pharmaceuticals Inc, Washington DC, VA.
25	Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
26	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
27	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
28	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
29	Product Information. Farydak (panobinostat). Novartis Pharmaceuticals, East Hanover, NJ.
30	Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
31	Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ.
32	Product Information. Macrilen (macimorelin). Aeterna Zentaris, Charleston, SC.
33	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.