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Compound Detail

CHEMBL576222

DIHYDROTETRABENAZINE
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COc1cc2c(cc1OC)[C@H]1C[C@@H](O)[C@H](CC(C)C)CN1CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL576222
Name DIHYDROTETRABENAZINE
Phase Preclinical
Structure Type MOL
InChI Key WEQLWGNDNRARGE-DJIMGWMZSA-N

Known Names

(+)-dihydrotetrabenzaine Dihydrotetrabenazine
3
Targets
14
Activities
2
Assay Types
11
PK Parameters
20
Publications
2
Known Names

Molecular Properties

319.4
MW (Da)
3.03
ALogP
4
HBA
1
HBD
41.9
PSA (Ų)
0.93
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Extended Properties

Molecular Formula C19H29NO3
MW 319.45
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 1.19

Activity Summary

Ki 12 meas. best 8.99
IC50 2 meas. best 7.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Synaptic vesicular amine transporter
CHEMBL4828
 Ki 8.99 8.585 1.0 6
Unchecked
CHEMBL612545
 Ki 8.72 8.72 1.9 3
Synaptic vesicular amine transporter
CHEMBL1893
 Ki 8.59 8.59 2.6 3
Synaptic vesicular amine transporter
CHEMBL4828
 IC50 7.83 7.765 14.7 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 736.33 ng.hr.mL-1 Rattus norvegicus
CL 53.7 mL.min-1.kg-1 Macaca mulatta
CL 1148.0 mL.min-1.kg-1 Mus musculus
CL 20.9 mL.min-1.kg-1 Homo sapiens
CL 74.5 mL.min-1.kg-1 Rattus norvegicus
Cmax 1211.9 nM Rattus norvegicus
T1/2 1.992 hr Homo sapiens
T1/2 0.08 hr Mus musculus
T1/2 0.58 hr Macaca mulatta
T1/2 1.61 hr Rattus norvegicus
Tmax 0.38 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Synaptic vesicular amine transporter Ki = 1.03 nM 8.99 Displacement of [125I]-iodovinyl-TBZ from VMAT2 in rat striatal homogenate after... 21531556
Unchecked Ki = 1.9 nM 8.72 Determining Vmat2 Inhibitory Activity of a Compound: Examples of techniques for ... -
Unchecked Ki = 1.9 nM 8.72 Determining Vmat2 Inhibitory Activity of a Compound: Examples of techniques for ... -
Unchecked Ki = 1.9 nM 8.72 Determining Vmat2 Inhibitory Activity of a Compound: Examples of techniques for ... -
Synaptic vesicular amine transporter Ki = 1.98 nM 8.7 Inhibition of VMAT2 in rat brain 33214818
Synaptic vesicular amine transporter Ki = 2.45 nM 8.61 Displacement of [125I]-iodovinyl-TBZ from VMAT2 in rat striatal membrane homogen... 19632829
Synaptic vesicular amine transporter Ki = 2.6 nM 8.59 Determining Vmat2 Inhibitory Activity of a Compound: Examples of techniques for ... -
Synaptic vesicular amine transporter Ki = 2.6 nM 8.59 Determining Vmat2 Inhibitory Activity of a Compound: Examples of techniques for ... -
Synaptic vesicular amine transporter Ki = 2.6 nM 8.59 Determining Vmat2 Inhibitory Activity of a Compound: Examples of techniques for ... -
Synaptic vesicular amine transporter Ki = 3.75 nM 8.43 Displacement of [3H]-DTBZ from VMAT2 in rat striatal membrane homogenates 19632829
Synaptic vesicular amine transporter Ki = 3.96 nM 8.4 Displacement of [3H]DHTBZ from Sprague-Dawley rat striatum VMAT2 after 1 hr by l... 21396745
Synaptic vesicular amine transporter Ki = 4.2 nM 8.38 Inhibition of [3H]-DHTBZ binding to VMAT2 from rat forebrain membranes 31774679
Synaptic vesicular amine transporter IC50 = 14.74 nM 7.83 Inhibition of [3H]DTBZ binding to VMAT2 in rat brain incubated for 30 mins by li... 34329999
Synaptic vesicular amine transporter IC50 = 20.01 nM 7.7 Inhibition of [3H]DA uptake at VMAT2 in rat striatal synaptosome incubated for 1... 34329999

Literature References

PubMed DOI Target Context # Activities
34329999 10.1016/j.ejmech.2021.113718 ADMET 16
34329999 10.1016/j.ejmech.2021.113718 Synaptic vesicular amine transporter 2
34329999 10.1016/j.ejmech.2021.113718 Rattus norvegicus 2
19632829 10.1016/j.bmcl.2009.07.048 Synaptic vesicular amine transporter 2
34329999 10.1016/j.ejmech.2021.113718 Cytochrome P450 2D6 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5724796 Fibroblast growth factor receptor 2 1
- 10.6019/CHEMBL5724796 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5724796 Aurora kinase A 1
- 10.6019/CHEMBL5724796 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5724796 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5724796 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5724796 Casein kinase I isoform delta 1
34329999 10.1016/j.ejmech.2021.113718 Cytochrome P450 2B6 1
34329999 10.1016/j.ejmech.2021.113718 Cytochrome P450 2C19 1
34329999 10.1016/j.ejmech.2021.113718 Cytochrome P450 2C9 1
34329999 10.1016/j.ejmech.2021.113718 Cytochrome P450 3A4 1
33214818 10.1021/acsmedchemlett.0c00202 Synaptic vesicular amine transporter 1
31774679 10.1021/acs.jmedchem.9b01237 Synaptic vesicular amine transporter 1
21531556 10.1016/j.bmcl.2011.03.113 Synaptic vesicular amine transporter 1

Data from ChEMBL 36 via Core Engine