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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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Maria Antonietta Maselli et al.
European journal of pharmacology, 723, 62-66 (2013-11-28)
The effect of two novel β3-adrenoceptor (β3-AR) agonists SP-1f and SP-1h on human colon circular smooth muscle contractility and β3-AR mRNA expression have been determined. β3-AR is ascertained co-participates to the control of the gut motility. Isometric tension on human
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
Martin Kulzer et al.
Biochemical and biophysical research communications, 424(2), 315-320 (2012-07-04)
Kir2.x channels form the molecular basis of cardiac I(K1) current and play a major role in cardiac electrophysiology. However, there is a substantial lack of selective Kir2 antagonists. We found the β(3)-adrenoceptor antagonist SR59230A to be an inhibitor of Kir2.x
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
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