SOLABEGRON HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H23ClN2O3.ClH
Molecular Weight	447.354
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.O[C@@H](CNCCNC1=CC=CC(=C1)C2=CC=CC(=C2)C(O)=O)C3=CC=CC(Cl)=C3

InChI

InChIKey=PMXCGBVBIRYFPR-FTBISJDPSA-N

InChI=1S/C23H23ClN2O3.ClH/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);1H/t22-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C23H23ClN2O3
Molecular Weight	410.893
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800013293 | http://www.velicept.com/pipeline/

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
GW427353 (solabegron), a novel, selective beta3-adrenergic receptor agonist, evokes bladder relaxation and increases micturition reflex threshold in the dog.	2007 Oct	17626794
A multicenter, double-blind, randomized, placebo-controlled trial of the β3-adrenoceptor agonist solabegron for overactive bladder.	2012 Nov	22695239

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Fri Dec 15 18:30:01 GMT 2023` Edited by `admin` on `Fri Dec 15 18:30:01 GMT 2023`
Record UNII	GU14FR8D4A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SOLABEGRON HYDROCHLORIDE

Official Name

English

Solabegron hydrochloride [WHO-DD]

Common Name

English

3'-((2-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)ETHYL)AMINO)BIPHENYL-3-CARBOXYLIC ACID HYDROCHLORIDE

Systematic Name

English

GW427353B

Code

English

(1,1'-BIPHENYL)-3-CARBOXYLIC ACID, 3'-((2-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)ETHYL)AMINO)-, HYDROCHLORIDE

Common Name

English

SOLABEGRON HYDROCHLORIDE [USAN]

Common Name

English

GW-427353B

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C48149