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Details

Stereochemistry RACEMIC
Molecular Formula C19H21ClNO4.Na
Molecular Weight 385.817
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRL-37344 SODIUM

SMILES

[Na+].C[C@H](CC1=CC=C(OCC([O-])=O)C=C1)NC[C@H](O)C2=CC(Cl)=CC=C2

InChI

InChIKey=SNJIJYKMYQRHRC-WJKBNZMCSA-M
InChI=1S/C19H22ClNO4.Na/c1-13(21-11-18(22)15-3-2-4-16(20)10-15)9-14-5-7-17(8-6-14)25-12-19(23)24;/h2-8,10,13,18,21-22H,9,11-12H2,1H3,(H,23,24);/q;+1/p-1/t13-,18+;/m1./s1

HIDE SMILES / InChI
Molecular Formula C19H21ClNO4
Molecular Weight 362.827
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

SB-206606 (better known as BRL-37344) was developed by Beecham Pharmaceuticals and is currently licensable from GlaxoSmithKline. SB-206606 is an agonist for the Beta-3 adrenergic receptor with an EC 50 value of 17 nM (human B3AR expressed in CHO cells). SB-206606 was in pre-clinical development as a potential treatment of Diabetes Mellitus, although such efforts have been discontinued. Recently it has also garnered some interest as a potential treatment for alcoholism.

CNS Activity

CNS Active
4002
Curator's Comment: BRL-37344 is systemically active and crosses the blood-brain barrier

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 430.0 nM [Ki]
Beta-3 adrenergic receptor
54
Target ID: P13945
Gene ID: 155.0
Gene Symbol: ADRB3
Target Organism: Homo sapiens (Human)
Agonist
2752
 17.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
β3-adrenoceptor-mediated increased circulating transaminase levels in mice treated with its agonist BRL 37344.
2010-10
Metabolic responses to BRL37344 and clenbuterol in soleus muscle and C2C12 cells via different atypical pharmacologies and beta2-adrenoceptor mechanisms.
2008-10
The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.
2007-11-14
Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats.
2007
Induction of beta3-adrenergic receptor functional expression following chronic stimulation with noradrenaline in neonatal rat cardiomyocytes.
2006-01
[Effect of beta3-adrenoreceptors agonist on beta3-adrenoreceptors expression and myocyte apoptosis in a rat model of heart failure].
2004-03
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
2004-02
5-HT(7) receptor and beta(2)-adrenoceptor share in the inhibition of porcine uterine contractility in a muscle layer-dependent manner.
2001-12-21
Beta2-adrenoceptor-mediated inhibition of field stimulation induced contractile responses of the smooth muscle of the rat prostate gland.
2001-11-09
Metabolic markers following beta-adrenoceptor agonist infusion in footshock-stressed rats.
2001-09
Enhancement of memory consolidation in chicks by beta(3)-adrenoceptor agonists.
2001-02-16
Norepinephrine induces vascular endothelial growth factor gene expression in brown adipocytes through a beta -adrenoreceptor/cAMP/protein kinase A pathway involving Src but independently of Erk1/2.
2000-05-05
beta1 to beta3 switch in control of cyclic adenosine monophosphate during brown adipocyte development explains distinct beta-adrenoceptor subtype mediation of proliferation and differentiation.
1999-09
Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells.
1999-04
Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors.
1997-02-01
Effects of beta-adrenoceptor subtype stimulation on obese gene messenger ribonucleic acid and on leptin secretion in mouse brown adipocytes differentiated in culture.
1997-02
Atypical beta-adrenergic receptor in 3T3-F442A adipocytes. Pharmacological and molecular relationship with the human beta 3-adrenergic receptor.
1991-10-25
Patents

Patents

20060019954
3
2620143
3
2891490
3
8906955
3
EP2620143B1
3
US20130197074
3
US20150374655
3
US9622996
3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In mice BRL-37344 has also being used i.p. https://www.ncbi.nlm.nih.gov/pubmed/20930473
Fasted rabbits: BRL-37344 was intravenously infused at 0.3 ugram.kg-1.min-1 (30 min)
Route of Administration: Intravenous
In Vitro Use Guide
BRL-37344 (10(-11)-10(-5) M) concentration-dependently decreased the amplitude of oxytocin-induced contractions of rat myometrial strips in vitro.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:34:40 GMT 2025
Edited
by admin
on Mon Mar 31 23:34:40 GMT 2025
Record UNII
H7P384313Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
B-169
Preferred Name English
BRL-37344 SODIUM
Common Name English
(R*,R*)-(±)-4-(2-((2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)PHENOXYACETIC ACID, SODIUM SALT
Systematic Name English
ACETIC ACID, (4-(2-((2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)PHENOXY)-, MONOSODIUM SALT, (R*,R*)-(±)-
Systematic Name English
SODIUM 2-(4-(2-((2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)PHENOXY)ACETATE
Systematic Name English
BRL-37344A
Code English
J830.645A
Code English
(±)-(R*,R*)-(4-(2-((2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)PHENOXY)-ACETIC ACID SODIUM
Systematic Name English
Code System Code Type Description
FDA UNII
H7P384313Z
Created by admin on Mon Mar 31 23:34:40 GMT 2025 , Edited by admin on Mon Mar 31 23:34:40 GMT 2025
PRIMARY
CAS
1017795-27-5
Created by admin on Mon Mar 31 23:34:40 GMT 2025 , Edited by admin on Mon Mar 31 23:34:40 GMT 2025
ALTERNATIVE
EPA CompTox
DTXSID80274368
Created by admin on Mon Mar 31 23:34:40 GMT 2025 , Edited by admin on Mon Mar 31 23:34:40 GMT 2025
PRIMARY
CAS
127299-93-8
Created by admin on Mon Mar 31 23:34:40 GMT 2025 , Edited by admin on Mon Mar 31 23:34:40 GMT 2025
PRIMARY
PUBCHEM
16219010
Created by admin on Mon Mar 31 23:34:40 GMT 2025 , Edited by admin on Mon Mar 31 23:34:40 GMT 2025
PRIMARY
Related Record Type Details
Structure of BRL-37344
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BRL-37344
ACTIVE MOIETY
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