TETRABENAZINE

/static/temp/default.svg

Search structure


Trade Names	TETRABENAZINE XENAZINE
Synonyms	NSC-169886 Nitoman RO 1-9569 RO-1-9569 RO-19569 Revocon Tetmodis Tetrabenazine Xenazine Xenazine 25
Status
Molecule Category	UNKNOWN
ATC	N07XX06
UNII	Z9O08YRN8O
EPA CompTox	DTXSID0042614


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	MKJIEFSOBYUXJB-UHFFFAOYSA-N
Smiles	COc1cc2c(cc1OC)C1CC(=O)C(CC(C)C)CN1CC2
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H27NO3
Molecular Weight	317.43
AlogP	3.24
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	4.0
Polar Surface Area	38.77
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Synaptic vesicular amine transporter inhibitor	INHIBITOR	DailyMed


Protein: Synaptic vesicular amine transporter Description: Synaptic vesicular amine transporter Organism : Homo sapiens Q05940 ENSG00000165646

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Voltage-gated ion channel Voltage-gated sodium channel	-	85000	-	-	7-55
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC18 family of vesicular amine transporters	-	-	-	8-54	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM	Cavia porcellus	7.0 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high-affinity sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 100 uM	Cavia porcellus	55.0 %
Inhibition of dopamine uptake at VMAT in bovine chromaffin granule ghosts	Bos taurus	4.0 nM
Displacement of [3H]DTBZ from VMAT2 dihydrotetrabenazine binding site in rat brain synaptic vesicle by scintillation counting	Rattus norvegicus	13.0 nM
Inhibition of [3H]dopamine uptake at VMAT2 in rat brain synaptic vesicle by liquid scintillation spectroscopy	Rattus norvegicus	54.0 nM
Displacement of [3H]MTBZ from VMAT2 in rat whole brain vesicles by liquid scintillation spectrophotometry	Rattus norvegicus	13.0 nM
Displacement of [3H]DHTBZ from Sprague-Dawley rat striatum VMAT2 after 1 hr by liquid scintillation counting	Rattus norvegicus	7.62 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	38.3 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.19 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.16 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.16 %

Related Entries

Cross References

Resources	Reference
ChEBI	64028
ChEMBL	CHEMBL117785
DrugBank	DB04844
FDA SRS	Z9O08YRN8O
Human Metabolome Database	HMDB0015592
Guide to Pharmacology	4834
KEGG	C11168
PharmGKB	PA140222719
SureChEMBL	SCHEMBL62026
ZINC	ZINC03875393

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).