Details of the Drug

General Information of Drug (ID: DMT3KB4)

Drug Name

Lobeline

Synonyms

lobeline; Lobelin; Inflatine; Lobeline [INN]; Lobelinum [INN-Latin]; Lobelina [INN-Spanish]; EINECS 202-012-3; BRN 0091533; AC1LEL62; ZINC56446; Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2R-(2alpha,6alpha(S*)))-; LS-88107

Indication

Disease Entry	ICD 11	Status	REF
Substance use disorder	6C4Z	Phase 2	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

337.5

Topological Polar Surface Area (xlogp)

3.8

Rotatable Bond Count (rotbonds)

6

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C22H27NO2
IUPAC Name: 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
Canonical SMILES: CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O
InChI: InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
InChIKey: MXYUKLILVYORSK-HBMCJLEFSA-N

Cross-matching ID

PubChem CID: 101616
ChEBI ID: CHEBI:48723
CAS Number: 90-69-7
DrugBank ID: DB05137
TTD ID: D01IVE
VARIDT ID: DR01063

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	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Substance use disorder

ICD Disease Classification

6C4Z

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

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Effects of VMAT2 inhibitors lobeline and GZ-793A on methamphetamine-induced changes in dopamine release, metabolism and synthesis in vivo. J Neurochem. 2013 Oct;127(2):187-98.
2	Design, synthesis and interaction at the vesicular monoamine transporter-2 of lobeline analogs: potential pharmacotherapies for the treatment of psychostimulant abuse. Curr Top Med Chem. 2011;11(9):1103-27.
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
4	Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8.
5	Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
6	VMAT2 Inhibitors and the Path to Ingrezza (Valbenazine). Prog Med Chem. 2018;57(1):87-111.
7	NBI-98854, a selective monoamine transport inhibitor for the treatment of tardive dyskinesia: A randomized, double-blind, placebo-controlled study. Mov Disord. 2015 Oct;30(12):1681-7.
8	Brain imaging of vesicular monoamine transporter type 2 in healthy aging subjects by 18F-FP-(+)-DTBZ PET. PLoS One. 2013 Sep 30;8(9):e75952.
9	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)