solabegron   Click here for help

GtoPdb Ligand ID: 9512

Synonyms: compound 38 [PMID: 16640337] | GW427353
Compound class: Synthetic organic
Comment: Solabegron (GW427353) is a highly potent and selective β3-adrenoceptor agonist [4]. β3 agonists (e.g. mirabegron and solabegron) failed to show efficacy for their original clinical indication, obesity/type 2 diabetes, but have been repurposed/repositioned for the treatment of the overactive bladder syndrome [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 81.59
Molecular weight 410.14
XLogP 4.56
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1cccc(c1)C(CNCCNc1cccc(c1)c1cccc(c1)C(=O)O)O
Isomeric SMILES Clc1cccc(c1)[C@H](CNCCNc1cccc(c1)c1cccc(c1)C(=O)O)O
InChI InChI=1S/C23H23ClN2O3/c24-20-8-2-6-18(13-20)22(27)15-25-10-11-26-21-9-3-5-17(14-21)16-4-1-7-19(12-16)23(28)29/h1-9,12-14,22,25-27H,10-11,15H2,(H,28,29)/t22-/m0/s1
InChI Key LLDXOPKUNJTIRF-QFIPXVFZSA-N
References
1. Biers SM, Reynard JM, Brading AF. (2006)
The effects of a new selective beta3-adrenoceptor agonist (GW427353) on spontaneous activity and detrusor relaxation in human bladder.
BJU Int, 98 (6): 1310-4. [PMID:17026593]
2. Michel MC, Korstanje C. (2016)
β3-Adrenoceptor agonists for overactive bladder syndrome: Role of translational pharmacology in a repositioning clinical drug development project.
Pharmacol Ther, 159: 66-82. [PMID:26808167]
3. Schemann M, Hafsi N, Michel K, Kober OI, Wollmann J, Li Q, Zeller F, Langer R, Lee K, Cellek S. (2010)
The beta3-adrenoceptor agonist GW427353 (Solabegron) decreases excitability of human enteric neurons via release of somatostatin.
Gastroenterology, 138 (1): 266-74. [PMID:19786030]
4. Uehling DE, Shearer BG, Donaldson KH, Chao EY, Deaton DN, Adkison KK, Brown KK, Cariello NF, Faison WL, Lancaster ME et al.. (2006)
Biarylaniline phenethanolamines as potent and selective beta3 adrenergic receptor agonists.
J Med Chem, 49 (9): 2758-71. [PMID:16640337]