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
Logarithm of the Partition Coefficient (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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Neuronal acetylcholine receptor subunit alpha-7 (CHRNA7) OTBUSUTE ACHA7_HUMAN Drug Response [3]
Potassium voltage-gated channel subfamily H member 2 (KCNH2) OTZX881H KCNH2_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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) 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 Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant. Eur J Pharmacol. 1999 Feb 5;366(2-3):301-8. doi: 10.1016/s0014-2999(98)00909-1.
4 Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.