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
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
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15684518 | https://www.rndsystems.com/products/brl-37344-sodium-salt_0948 | https://www.ncbi.nlm.nih.gov/pubmed/23955701 | https://www.ncbi.nlm.nih.gov/pubmed/25462854 | https://www.ncbi.nlm.nih.gov/pubmed/1345889 |https://www.ncbi.nlm.nih.gov/pubmed/23890664 | http://adisinsight.springer.com/drugs/800006890 | https://www.ncbi.nlm.nih.gov/pubmed/12237641 | https://www.ncbi.nlm.nih.gov/pubmed/8773403 | https://www.ncbi.nlm.nih.gov/pubmed/20930473
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15684518 | https://www.rndsystems.com/products/brl-37344-sodium-salt_0948 | https://www.ncbi.nlm.nih.gov/pubmed/23955701 | https://www.ncbi.nlm.nih.gov/pubmed/25462854 | https://www.ncbi.nlm.nih.gov/pubmed/1345889 |https://www.ncbi.nlm.nih.gov/pubmed/23890664 | http://adisinsight.springer.com/drugs/800006890 | https://www.ncbi.nlm.nih.gov/pubmed/12237641 | https://www.ncbi.nlm.nih.gov/pubmed/8773403 | https://www.ncbi.nlm.nih.gov/pubmed/20930473
BRL-37344 is a selective β3-adrenergic receptor agonist originated by GlaxoSmithKline. Ki value is 287 nM for β3 receptor, 1750 nM for β1 receptor and 1120 nM for β2 receptor. BRL-37344 can decrease nerve-evoked contractions in human detrusor smooth muscle isolated strips, it can also stimulate fuel oxidation by soleus muscle in vitro. In fasted rabbits, BRL-37344 significantly increased plasma nonesterified fatty acids (NEFA) levels through β3-adrenoceptor. However, BRL-37344 had no effect on plasma glucose levels. In mice, BRL-37344 increased circulating transaminase levels through activation of β3-adrenoceptor. BRL-37344 increases glucose transport into L6 myocytes through a mechanism different from that of insulin. But preclinical for Diabetes mellitus was discontinued.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 430.0 nM [Ki] | |||
Target ID: P13945 Gene ID: 155.0 Gene Symbol: ADRB3 Target Organism: Homo sapiens (Human) |
17.0 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Atypical beta-adrenergic receptor in 3T3-F442A adipocytes. Pharmacological and molecular relationship with the human beta 3-adrenergic receptor. | 1991 Oct 25 |
|
| Effects of beta-adrenoceptor subtype stimulation on obese gene messenger ribonucleic acid and on leptin secretion in mouse brown adipocytes differentiated in culture. | 1997 Feb |
|
| Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors. | 1997 Feb 1 |
|
| Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells. | 1999 Apr |
|
| 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 Sep |
|
| 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 May 5 |
|
| Enhancement of memory consolidation in chicks by beta(3)-adrenoceptor agonists. | 2001 Feb 16 |
|
| Beta2-adrenoceptor-mediated inhibition of field stimulation induced contractile responses of the smooth muscle of the rat prostate gland. | 2001 Nov 9 |
|
| Induction of beta3-adrenergic receptor functional expression following chronic stimulation with noradrenaline in neonatal rat cardiomyocytes. | 2006 Jan |
|
| Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. | 2007 |
|
| The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder. | 2007 Nov 14 |
|
| Metabolic responses to BRL37344 and clenbuterol in soleus muscle and C2C12 cells via different atypical pharmacologies and beta2-adrenoceptor mechanisms. | 2008 Oct |
|
| β3-adrenoceptor-mediated increased circulating transaminase levels in mice treated with its agonist BRL 37344. | 2010 Oct |
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
The effect of SB-206606 on the liver uptake of Brown Adipose Tissue in the Liver (BAT/L) was examined in mice. Obese mice and mice with Diabetes Mellitus (DM) received an intraperitoneal injection of SB-206606 (2.5 mg/kg) three times per week for two weeks. After two weeks of treatment with SB-206606, there was a significant increase in BAT/L for both obese mice (6.64±1.97) and DM mice (5.25±1.50) compared with the controls without SB-206606 treatment (4.20±1.13 in obese control mice, P = 0.010; 2.32±1.01 in DM control mice, P = 0.004). In normal control mice, even a single-dose of SB-206606 would significantly increase BAT/L compared with the untreated controls (31.74±21.39 versus 7.61±1.44, P = 0.002).
Route of Administration:
Intraperitoneal
Human B3-AR cDNA was cloned from total RNA extracted from human neuroblastoma cell SK-N-MC (ATCC HTB 10), and inserted into a pKCN1 plasmid, which was subsequently transformed into Chinese Hamster Ovary Cell line (CHO-K1). B3-AR agonistic activity was assessed by measurement of cAMP accumulation level in CHO cells expressing human b3-AR. Cells were treated with varying concentrations of SB-206606 and the EC50 value was determined as the concentration required to achieve 50% of cAMP accumulation. BRL 37344 exhibited agonistic activity with EC50 17 nM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:01:17 GMT 2023
by
admin
on
Sat Dec 16 11:01:17 GMT 2023
|
| Record UNII |
H7P384313Z
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
H7P384313Z
Created by
admin on Sat Dec 16 11:01:18 GMT 2023 , Edited by admin on Sat Dec 16 11:01:18 GMT 2023
|
PRIMARY | |||
|
1017795-27-5
Created by
admin on Sat Dec 16 11:01:18 GMT 2023 , Edited by admin on Sat Dec 16 11:01:18 GMT 2023
|
ALTERNATIVE | |||
|
DTXSID80274368
Created by
admin on Sat Dec 16 11:01:18 GMT 2023 , Edited by admin on Sat Dec 16 11:01:18 GMT 2023
|
PRIMARY | |||
|
127299-93-8
Created by
admin on Sat Dec 16 11:01:18 GMT 2023 , Edited by admin on Sat Dec 16 11:01:18 GMT 2023
|
PRIMARY | |||
|
16219010
Created by
admin on Sat Dec 16 11:01:18 GMT 2023 , Edited by admin on Sat Dec 16 11:01:18 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |