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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H23ClN2O3
Molecular Weight 410.8941
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOLABEGRON

SMILES

c1cc(cc(c1)C(=O)O)-c2cccc(c2)NCCNC[C@@]([H])(c3cccc(c3)Cl)O

InChI

InChIKey=LLDXOPKUNJTIRF-QFIPXVFZSA-N
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

HIDE SMILES / InChI

Molecular Formula C23H23ClN2O3
Molecular Weight 410.8941
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Solabegron (GW427353), a beta-3 adrenoceptor agonist, is in development with AltheRx (now Velicept Therapeutics) for the treatment of irritable bowel syndrome (IBS) and overactive bladder (OAB). Solabegron was discovered and first developed by GlaxoSmithKline. It was acquired by AltheRx, which merged with Velicept in 2015 to continue development of the program. Solabegron has been tested in over 800 study subjects in a twice-a-day formulation and demonstrated efficacy in the treatment of OAB as well as IBS. A once daily formulation designed to optimize patient convenience as well as efficacy has been developed and is currently being evaluated in a phase 2b dose ranging clinical trial. A Phase 2b dose ranging study with the twice daily formulation also began enrollment in Q1 2018.

Approval Year

PubMed

PubMed

TitleDatePubMed
GW427353 (solabegron), a novel, selective beta3-adrenergic receptor agonist, evokes bladder relaxation and increases micturition reflex threshold in the dog.
2007 Oct
A multicenter, double-blind, randomized, placebo-controlled trial of the β3-adrenoceptor agonist solabegron for overactive bladder.
2012 Nov
Patents

Sample Use Guides

Women with OAB: Solabegron 50 mg (n=88), solabegron 125 mg (n=85), or placebo (n=85)-all twice daily-were administered. Solabegron 125 mg produced a statistically significant difference in percent change from baseline to week 8 in incontinence episodes over 24h when compared with placebo. Solabegron 125 mg treatment also showed statistically significant reductions from baseline to weeks 4 and 8 in micturitions over 24 h and a statistically significant increase from baseline to week 8 in urine volume voided.
Route of Administration: Oral
Solabegron (GW427353) stimulated cAMP accumulation in Chinese hamster ovary cells expressing the human beta3-AR, with an EC50 value of 22 +/- 6 nM and an intrinsic activity 90% of isoproterenol. At concentrations of 10,000 nM, GW427353 produced a minimal response in cells expressing either beta1-ARs or beta2-ARs (maximum response <10% of that to isoproterenol).
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:53:31 UTC 2021
Edited
by admin
on Sat Jun 26 08:53:31 UTC 2021
Record UNII
55P6YH9O6N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SOLABEGRON
INN   WHO-DD  
INN  
Official Name English
(1,1'-BIPHENYL)-3-CARBOXYLIC ACID, 3'-((2-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)ETHYL)AMINO)-
Common Name English
SOLABEGRON [INN]
Common Name English
3'-((2-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)ETHYL)AMINO)BIPHENYL-3-CARBOXYLIC ACID
Systematic Name English
SOLABEGRON [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL208427
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
FDA UNII
55P6YH9O6N
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
WIKIPEDIA
SOLABEGRON
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
EPA CompTox
252920-94-8
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
MESH
C523977
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
INN
8424
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
PUBCHEM
9887812
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
NCI_THESAURUS
C96754
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
DRUG BANK
DB06190
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
CAS
252920-94-8
Created by admin on Sat Jun 26 08:53:31 UTC 2021 , Edited by admin on Sat Jun 26 08:53:31 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY