darigabat   Click here for help

GtoPdb Ligand ID: 9798

Synonyms: example 4 [WO2014091368] | PF-06372865 | PF06372865
Compound class: Synthetic organic
Comment: Darigabat (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 this compound 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
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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
11498 darigabat
Synonyms Click here for help
example 4 [WO2014091368] | PF-06372865 | PF06372865
Database Links Click here for help
BindingDB Ligand 144227
ChEMBL Ligand CHEMBL3647536
GtoPdb PubChem SID 354702270
PubChem CID 76287260
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UniChem Compound Search for chemical match using the InChIKey PTTQXDBPTFOCMT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PTTQXDBPTFOCMT-UHFFFAOYSA-N