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S8688

Sigma-Aldrich

SR 59230A

≥98% (HPLC), powder, β3-Adrenoceptor antagonist

Synonym(s):

3-(2-Ethylphenoxy)-1-[[(1S)-1,2,3,4-tetrahydronaphth-1-yl]amino]-(2S)-2-propanol oxalate salt

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About This Item

Empirical Formula (Hill Notation):
C21H27NO2 · C2H2O4
CAS Number:
174689-39-5
Molecular Weight:
415.48
MDL number:
MFCD00940163
UNSPSC Code:
12352200
PubChem Substance ID:
24278715
NACRES:
NA.77
Pricing and availability is not currently available.

Product Name

SR 59230A, ≥98% (HPLC), powder

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: >10 mg/mL
H2O: insoluble

originator

Sanofi Aventis

SMILES string

OC(=O)C(O)=O.CCc1ccccc1OC[C@@H](O)CN[C@H]2CCCc3ccccc23

InChI

1S/C21H27NO2.C2H2O4/c1-2-16-8-4-6-13-21(16)24-15-18(23)14-22-20-12-7-10-17-9-3-5-11-19(17)20;3-1(4)2(5)6/h3-6,8-9,11,13,18,20,22-23H,2,7,10,12,14-15H2,1H3;(H,3,4)(H,5,6)/t18-,20-;/m0./s1

InChI key

XTBQNQMNFXNGLR-MKSBGGEFSA-N

Gene Information

human ... ADRB3(155)

Application

SR 59230A was used in the identification of β-adrenoceptors in rat aorta.3 It was tested as a potential therapeutic agent in improving cardiac function in rat model of heart failure.4

Biochem/physiol Actions

SR 59230A is a β3-adrenoceptor antagonist. It has high affinity for the β3 adrenoceptors occurring in human gut that affect the function of human colonic circular smooth muscle.1 It is reported that SR 59230A inhibits the Kir2.1-2.3 cardiac potassium channels.2

Features and Benefits

This compound is featured on the β-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000277830
0000244751
0000277830
0000244751
0000148562

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Maura Calvani et al.
Frontiers in immunology, 11, 2098-2098 (2020-09-29)
Understanding the mechanisms of immune tolerance is currently one of the most important challenges of scientific research. Pregnancy affects the immune system balance, leading the host to tolerate embryo alloantigens. Previous reports demonstrated that β-adrenergic receptor (β-AR) signaling promotes immune
F De Ponti et al.
British journal of pharmacology, 117(7), 1374-1376 (1996-04-01)
The role of beta 3-adrenoceptors in human colonic circular smooth muscle was assessed in vitro by use of the beta 3-selective antagonist SR 59230A. Isoprenaline, in the presence of the selective beta-adrenoceptor antagonists CGP 20712A (beta 1) and ICI 118551
Maura Calvani et al.
British journal of pharmacology, 176(14), 2509-2524 (2019-03-16)
Stress-related catecholamines have a role in cancer and β-adrenoceptors; specifically, β2 -adrenoceptors have been identified as new targets in treating melanoma. Recently, β3 -adrenoceptors have shown a pleiotropic effect on melanoma micro-environment leading to cancer progression. However, the mechanisms by
Run-tao Gan et al.
Chinese medical journal, 120(24), 2250-2255 (2008-01-03)
Stimulation of the heart beta 3-adrenoceptor (AR) may result in a negative inotropic effect. Being up-regulated, beta 3-AR plays a more important role in the regulation of cardiac function during heart failure. However, the effect of chronic blocking of beta
Nataraj Brahmadevara et al.
British journal of pharmacology, 142(4), 781-787 (2004-06-19)
1. The alpha(1)-adrenoceptor antagonist properties of the beta-adrenoceptor nonconventional partial agonist, CGP 12177A, was investigated in functional assays in rat aorta and in radioligand binding assays in rat cerebral cortical membranes. In addition, binding affinities of other beta-adrenoceptor ligands were
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