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Showing metabocard for Tetrabenazine (HMDB0015592)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-09-27 08:28:00 UTC
HMDB IDHMDB0015592
Secondary Accession Numbers
  • HMDB15592
Metabolite Identification
Common NameTetrabenazine
DescriptionA drug formerly used as an antipsychotic but now used primarily in the treatment of various movement disorders including tardive dyskinesia. Tetrabenazine blocks uptake into adrenergic storage vesicles and has been used as a high affinity label for the vesicle transport system. [PubChem]
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2,4,6,7,11b-hexahydro-3-Isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-oneChEBI
2-oxo-3-Isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11BH-benzo[a]quinolizineChEBI
2-oxo-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizineChEBI
ro 1-9569HMDB
TBZHMDB
Tetra benazinHMDB
TetrabenzaineHMDB
TetrabenzineHMDB
Tetrabenazine orphan brandMeSH
Cambridge laboratories brand OF tetrabenazineMeSH
Orphan brand OF tetrabenazineMeSH
Roche brand OF tetrabenazineMeSH
Shire brand OF tetrabenazineMeSH
XenazineMeSH
NitomanMeSH
Chemical FormulaC19H27NO3
Average Molecular Weight317.4226
Monoisotopic Molecular Weight317.199093735
IUPAC Name9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
Traditional Nametetrabenazine
CAS Registry Number58-46-8
SMILES
COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1
InChI Identifier
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
InChI KeyMKJIEFSOBYUXJB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrahydroisoquinolines
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • Piperidinone
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Cyclic ketone
  • Ether
  • Azacycle
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point128 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.36 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP3.23ALOGPS
logP3.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)18.24ChemAxon
pKa (Strongest Basic)7.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.31 m³·mol⁻¹ChemAxon
Polarizability36.59 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-02d6ea72dcc42a44288eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5269000000-f1240b2a09dcced1c899View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9430000000-cd11325cad96834bf22bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-484fd7bae49c0273c317View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-7059000000-cbb7a83dafd4d674e753View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uec-9270000000-5581f9758fcb31092e0cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04844 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04844 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04844
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5796
KEGG Compound IDC11168
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrabenazine
METLIN IDNot Available
PubChem Compound6018
PDB IDNot Available
ChEBI ID64028
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. [PubMed:9040721 ]
  2. Guay DR: Tetrabenazine, a monoamine-depleting drug used in the treatment of hyperkinetic movement disorders. Am J Geriatr Pharmacother. 2010 Aug;8(4):331-73. doi: 10.1016/j.amjopharm.2010.08.006. [PubMed:20869622 ]

Enzymes

Enzyme Details
1. Cytochrome P450 2D6
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Poon LH, Kang GA, Lee AJ: Role of tetrabenazine for Huntington's disease-associated chorea. Ann Pharmacother. 2010 Jun;44(6):1080-9. doi: 10.1345/aph.1M582. Epub 2010 May 4. [PubMed:20442355 ]
Enzyme Details
2. Synaptic vesicular amine transporter
General function:
Involved in transmembrane transport
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. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular weight:
55712.1
References
  1. Zheng G, Dwoskin LP, Crooks PA: Vesicular monoamine transporter 2: role as a novel target for drug development. AAPS J. 2006 Nov 10;8(4):E682-92. [PubMed:17233532 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Kim YS, Shin JH, Hall FS, Linden DJ: Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8. doi: 10.1523/JNEUROSCI.0468-09.2009. [PubMed:19571144 ]
  4. Goland R, Freeby M, Parsey R, Saisho Y, Kumar D, Simpson N, Hirsch J, Prince M, Maffei A, Mann JJ, Butler PC, Van Heertum R, Leibel RL, Ichise M, Harris PE: 11C-dihydrotetrabenazine PET of the pancreas in subjects with long-standing type 1 diabetes and in healthy controls. J Nucl Med. 2009 Mar;50(3):382-9. doi: 10.2967/jnumed.108.054866. Epub 2009 Feb 17. [PubMed:19223416 ]
  5. Gros Y, Schuldiner S: Directed evolution reveals hidden properties of VMAT, a neurotransmitter transporter. J Biol Chem. 2010 Feb 12;285(7):5076-84. doi: 10.1074/jbc.M109.081216. Epub 2009 Dec 10. [PubMed:20007701 ]
  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. [PubMed:20135628 ]