mesoridazine   Click here for help

GtoPdb Ligand ID: 7227

Synonyms: NC-123 | Serentil® | TPS-23
Approved drug
mesoridazine is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: The approved drug contains a racemic mixture of enantiomers [1]. The four possible isomers are depicted in PubChem CID 76960490. We show the non-isomeric molecule to represent this mixture.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 68.06
Molecular weight 386.15
XLogP 3.92
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCCCC1CCN1c2ccccc2Sc2c1cc(cc2)S(=O)C
Isomeric SMILES CN1CCCCC1CCN1c2ccccc2Sc2c1cc(cc2)S(=O)C
InChI InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
Bioactivity Comments
Note that the affinity values in the table below were produced using a specific stereoisomer of the mesoridazine, referred to as isomer 2 in [1] (which has IUPAC name 2-[(R)-methanesulfinyl]-10-{2-[(2S)-1-methylpiperidin-2-yl]ethyl}-10H-phenothiazine).
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
D2 receptor Hs Antagonist Antagonist 8.7 pKi - 1
pKi 8.7 (Ki 2.2x10-9 M) [1]
D3 receptor Hs Antagonist Antagonist 7.6 pKi - 1
pKi 7.6 (Ki 2.3x10-8 M) [1]
5-HT2A receptor Hs Antagonist Antagonist 7.3 pKi - 1
pKi 7.3 (Ki 5.5x10-8 M) [1]
D1 receptor Hs Antagonist Antagonist 7.0 pKi - 1
pKi 7.0 (Ki 1.03x10-7 M) [1]
5-HT1A receptor Hs Antagonist Antagonist 7.0 pKi - 1
pKi 7.0 (Ki 1.05x10-7 M) [1]
5-HT2C receptor Hs Antagonist Antagonist 6.4 pKi - 1
pKi 6.4 (Ki 4.12x10-7 M) [1]