PF-06372865   Click here for help

GtoPdb Ligand ID: 9798

Synonyms: darigabat (proposed INN) | example 4 [WO2014091368] | PF06372865
Compound class: Synthetic organic
Comment: PF-06372865 is an orally active, GABAA receptor positive allosteric modulator, that selectively targets GABAA receptors containing α2/3/5 subunits over receptors containing α1 subunits [1,3]. The α1 subunit is associated with the (undesirable) sedative effects of benzodiazepine drugs, whilst the α2/3 subunits contribute to their anxiolytic and analgesic activities and the α5 subunit to effects on memory function. The chemical structure of PF-06372865 is claimed as 'Example 4' in patent WO2014091368 [2]. Pfizer are developing PF-06372865 for clinical potential in the treatment of chronic pain [4] and photosensitive epilepsy, but have terminated development in generalized anxiety disorder.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 95.35
Molecular weight 440.13
XLogP 4.53
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(ccc1c1cc(ccc1F)c1cnnc2c1ncn2CC)S(=O)(=O)CC
Isomeric SMILES COc1cc(ccc1c1cc(ccc1F)c1cnnc2c1ncn2CC)S(=O)(=O)CC
InChI InChI=1S/C22H21FN4O3S/c1-4-27-13-24-21-18(12-25-26-22(21)27)14-6-9-19(23)17(10-14)16-8-7-15(11-20(16)30-3)31(28,29)5-2/h6-13H,4-5H2,1-3H3
InChI Key PTTQXDBPTFOCMT-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
7-ethyl-4-[3-(4-ethylsulfonyl-2-methoxyphenyl)-4-fluorophenyl]imidazo[4,5-c]pyridazine
Synonyms Click here for help
darigabat (proposed INN) | example 4 [WO2014091368] | PF06372865
Database Links Click here for help
BindingDB Ligand 144227
ChEMBL Ligand CHEMBL3647536
GtoPdb PubChem SID 354702270
PubChem CID 76287260
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