BF-1   Click here for help

GtoPdb Ligand ID: 8424

Compound class: Synthetic organic
Comment: BF-1 is a selective antagonist of the 5-HT2B receptor, being investigated preclinically as an anti-migraine therapeutic [1]. Because this compound lacks high affinities for other monoamine receptors it should have fewer monoanimergic side effects than reported for previously used and withdrawn 5-HT2B antagonists such as methysergide and pizotifen. BF-1 is the result of structural modification of the chemical scaffold of methixene, a compound with high affinity for 5-HT2A, 2B, 2C, histamine H1, adrenaline α1A and muscarinic M2 receptors [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 47
Molecular weight 367.16
XLogP 4.29
No. Lipinski's rules broken 0
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Canonical SMILES CCOc1ccc2c(c1)Sc1c(C2=C2CCN(CC2)C)c(OC)ccc1
Isomeric SMILES CCOc1ccc2c(c1)Sc1c(C2=C2CCN(CC2)C)c(OC)ccc1
InChI InChI=1S/C22H25NO2S/c1-4-25-16-8-9-17-20(14-16)26-19-7-5-6-18(24-3)22(19)21(17)15-10-12-23(2)13-11-15/h5-9,14H,4,10-13H2,1-3H3
Bioactivity Comments
Binding affinities for BF-1 across the serotinin receptor family and a range of non-serotonin monoaminergic receptors are reported in [1]. We show the affinity for the 2A subtype as the next closest affinity to the 2B receptor in the table below. All other receptors tested had lower affinities for BF-1.
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2B receptor Primary target of this compound Hs Antagonist Antagonist 10.1 pKi - 1
pKi 10.1 [1]
5-HT2A receptor Hs Antagonist Antagonist 8.6 pKi - 1
pKi 8.6 [1]