9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

• ChemBase ID: 4388
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: O=C1C(CN2C(C1)c1c(CC2)cc(OC)c(OC)c1)CC(C)C
• Canonical SMILES: COc1cc2c(cc1OC)CCN1C2CC(=O)C(C1)CC(C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
• IUPAC Traditional name: tetrabenazine
• Brand Name: Nitoman; Regulin; Rubigen; Xenazine
• Synonyms: Tetra benazin; Tetrabenazina [inn-spanish]; Tetrabenazinum [inn-latin]; Tetrabenzaine; Tetrabenzine; Tetrabenazine; (3R,11bR)-rel-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one; cis-2-Oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine; (+/-)-Tetrabenazine; NSC 169886; NSC 172187; Ro 1-9569; Rubigen

Database IDs

• CAS Number: 58-46-8
• PubChem SID: 160967820; 46506426
• PubChem CID: 6018

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.239992
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.4955962
• LogD (pH = 7.4): 3.094543
• Log P: 3.4010618
• Molar Refractivity: 91.3074 cm^3
• Polarizability: 35.678963 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.23
• LOG S: -2.94
• Solubility (Water): 3.61e-01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 128-130°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB04844

• Drug Groups: approved
• Description: A 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]
• Indication: For the symptomatical treatment of hyperkinetic movement disorder.
• Affected Organisms: Humans and other mammals
• Biotransformation: CYP2D6 mediated hepatic metabolism.
• Protein Binding: 82-85%
• Elimination: After oral administration, tetrabenazine is extensively hepatically metabolized, and the metabolites are primarily renally eliminated. In a mass balance study in 6 healthy volunteers, approximately 75% of the dose was excreted in the urine and fecal recovery accounted for approximately 7-16% of the dose. Urinary excretion of α-HTBZ or β-HTBZ (the major metabolites)accounted for less than 10% of the administered dose.
• Clearance: Tetrabenazine is cleared renally and fecally.
• References: Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. [Pubmed]
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - T284000

Dopamine depleting agent. An antidyskinetic; antipsychotic.

REFERENCES

• Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. Pubmed
• Schwartz, et al.: Biochem. Pharmacol., 15, 645 (1966)
• Janovic, J., et al.: Ann. Neurol., 11, 41 (1966)
• Janovic, J., et al.: Neurology, 38, 391 (1966)