NAV

Solabegron

Identification

Generic Name
Solabegron
DrugBank Accession Number
DB06190
Background

Solabegron (GW-427,353) is a selective β3 adrenoceptor agonist being developed for the treatment of overactive bladder and irritable bowel syndrome.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 410.9
Monoisotopic: 410.1397203
Chemical Formula
C23H23ClN2O3
Synonyms
  • Solabegron
External IDs
  • GW 427353
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Pharmacology

Indication

Investigated for use/treatment in diabetes mellitus type 2, irritable bowel syndrome (IBS), and urinary incontinence.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-3 adrenergic receptor
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcebutololThe therapeutic efficacy of Solabegron can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Solabegron is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Solabegron is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Solabegron.
AclidiniumThe risk or severity of Tachycardia can be increased when Solabegron is combined with Aclidinium.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Solabegron hydrochlorideGU14FR8D4A451470-34-1PMXCGBVBIRYFPR-FTBISJDPSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Benzoic acids / Phenylalkylamines / Aniline and substituted anilines / Benzoyl derivatives / Secondary alkylarylamines / Chlorobenzenes / Aryl chlorides / Secondary alcohols / 1,2-aminoalcohols / Amino acids
show 8 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Amino acid / Amino acid or derivatives / Aniline or substituted anilines / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Aryl chloride
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
55P6YH9O6N
CAS number
252920-94-8
InChI Key
LLDXOPKUNJTIRF-QFIPXVFZSA-N
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
IUPAC Name
3'-[(2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino]-[1,1'-biphenyl]-3-carboxylic acid
SMILES
[H][C@](O)(CNCCNC1=CC(=CC=C1)C1=CC(=CC=C1)C(O)=O)C1=CC=CC(Cl)=C1

References

General References
  1. Grudell AB, Camilleri M, Jensen KL, Foxx-Orenstein AE, Burton DD, Ryks MD, Baxter KL, Cox DS, Dukes GE, Kelleher DL, Zinsmeister AR: Dose-response effect of a beta3-adrenergic receptor agonist, solabegron, on gastrointestinal transit, bowel function, and somatostatin levels in health. Am J Physiol Gastrointest Liver Physiol. 2008 May;294(5):G1114-9. doi: 10.1152/ajpgi.00051.2008. Epub 2008 Mar 27. [Article]
  2. Hicks A, McCafferty GP, Riedel E, Aiyar N, Pullen M, Evans C, Luce TD, Coatney RW, Rivera GC, Westfall TD, Hieble JP: GW427353 (solabegron), a novel, selective beta3-adrenergic receptor agonist, evokes bladder relaxation and increases micturition reflex threshold in the dog. J Pharmacol Exp Ther. 2007 Oct;323(1):202-9. Epub 2007 Jul 12. [Article]
PubChem Compound
9887812
PubChem Substance
347827760
ChemSpider
8063484
BindingDB
50002595
ChEBI
141346
ChEMBL
CHEMBL208427
ZINC
ZINC000001547346
Wikipedia
Solabegron

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedDiagnosticIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentOveractive Bladder Syndrome (OABS)3
1CompletedDiagnosticIrritable Bowel Syndrome (IBS)1
1CompletedTreatmentHealthy Subjects, Overactive Bladder1
1CompletedTreatmentOveractive Bladder Syndrome (OABS)2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00167 mg/mLALOGPS
logP3.67ALOGPS
logP1.61Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.01Chemaxon
pKa (Strongest Basic)9.02Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area81.59 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity116.75 m3·mol-1Chemaxon
Polarizability45.24 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9399
Blood Brain Barrier+0.7481
Caco-2 permeable-0.5411
P-glycoprotein substrateSubstrate0.7467
P-glycoprotein inhibitor INon-inhibitor0.8542
P-glycoprotein inhibitor IINon-inhibitor0.8907
Renal organic cation transporterNon-inhibitor0.7937
CYP450 2C9 substrateNon-substrate0.7838
CYP450 2D6 substrateNon-substrate0.8299
CYP450 3A4 substrateNon-substrate0.6663
CYP450 1A2 substrateInhibitor0.5132
CYP450 2C9 inhibitorNon-inhibitor0.6705
CYP450 2D6 inhibitorNon-inhibitor0.6447
CYP450 2C19 inhibitorNon-inhibitor0.6671
CYP450 3A4 inhibitorNon-inhibitor0.8394
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7415
Ames testNon AMES toxic0.5071
CarcinogenicityNon-carcinogens0.7194
BiodegradationNot ready biodegradable0.9856
Rat acute toxicity2.5218 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7658
hERG inhibition (predictor II)Inhibitor0.5771
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xv-0019400000-f6d9237a3c6e5dd4200c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-3039800000-ce84706df025d42fabc9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0035-0439100000-c75e97bc55e92d0e94f8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-5092100000-2c7302b5408bc42115eb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01po-0942100000-d81d8326f4847de7a100
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-868497d5cda003e83499
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.37323
predicted
DeepCCS 1.0 (2019)
[M+H]+195.73122
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.04347
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-3 adrenergic receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da
References
  1. Grudell AB, Camilleri M, Jensen KL, Foxx-Orenstein AE, Burton DD, Ryks MD, Baxter KL, Cox DS, Dukes GE, Kelleher DL, Zinsmeister AR: Dose-response effect of a beta3-adrenergic receptor agonist, solabegron, on gastrointestinal transit, bowel function, and somatostatin levels in health. Am J Physiol Gastrointest Liver Physiol. 2008 May;294(5):G1114-9. doi: 10.1152/ajpgi.00051.2008. Epub 2008 Mar 27. [Article]

Drug created at March 19, 2008 16:16 / Updated at February 21, 2021 18:52