Synonym
SR-59230A oxalate; SR-59230A; SR 59230A; SR59230A;
IUPAC/Chemical Name
1-(2-Ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-(2S)-2-propanol oxalate
InChi Key
XTBQNQMNFXNGLR-MKSBGGEFSA-N
InChi Code
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
SMILES Code
O[C@@H](CN[C@H]1CCCC2=C1C=CC=C2)COC3=CC=CC=C3CC.O=C(O)C(O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
SR59230A is a β3-adrenergic receptor antagonist with IC50s of 40, 408, and 648 nM for β3, β1, and β2 receptors, respectively.
In vitro activity:
SR-59230A displayed partial agonist properties in some cells and acted as a full agonist in others. It antagonized cAMP increases in adipocytes but showed agonist effects in a microphysiometer. In mouse ileum, it relaxed smooth muscle independently of cAMP levels. These results suggest SR-59230A exhibits dual agonist and antagonist actions at mouse beta(3)-adrenoceptors, possibly through cAMP-independent pathways.
Reference: J Pharmacol Exp Ther. 2005 Mar;312(3):1064-74. https://pubmed.ncbi.nlm.nih.gov/15574684/
In vivo activity:
SR-59230A exerts beneficial effects on right ventricular performance in rats with monocrotaline (MCT)-induced pulmonary arterial hypertension (PAH). Blocking β3-AR with SR-59230A may alleviate the structural changes and inflammatory infiltration to the lung as a result of reduced oxidative stress. SR-59230A suppressed the elevated expression of endothelial nitric oxide and alleviated inflammatory infiltration to the lung under PAH conditions.
Reference: Exp Ther Med. 2020 Jan;19(1):489-498. https://pubmed.ncbi.nlm.nih.gov/31853320/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
31.3 |
75.21 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
415.49
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Pettersson US, Sandberg M, Jansson L. Two-week treatment with the β₃-adrenoceptor antagonist SR59230A normalizes the increased pancreatic islet blood flow in type 2 diabetic GK rats. Diabetes Obes Metab. 2012 Oct;14(10):960-2. doi: 10.1111/j.1463-1326.2012.01616.x. Epub 2012 May 28. PMID: 22564532.
2. Hutchinson DS, Sato M, Evans BA, Christopoulos A, Summers RJ. Evidence for pleiotropic signaling at the mouse beta3-adrenoceptor revealed by SR59230A [3-(2-Ethylphenoxy)-1-[(1,S)-1,2,3,4-tetrahydronapth-1-ylamino]-2S-2-propanol oxalate]. J Pharmacol Exp Ther. 2005 Mar;312(3):1064-74. doi: 10.1124/jpet.104.076901. Epub 2004 Dec 1. PMID: 15574684.
3. Sun J, Cheng J, Ding X, Chi J, Yang J, Li W. β3 adrenergic receptor antagonist SR59230A exerts beneficial effects on right ventricular performance in monocrotaline-induced pulmonary arterial hypertension. Exp Ther Med. 2020 Jan;19(1):489-498. doi: 10.3892/etm.2019.8236. Epub 2019 Nov 22. PMID: 31853320; PMCID: PMC6909721.
4. Zhao QQ, Jing JN, Li HQ, Liu R, Li XP, Cui XL. [Effect of β3-AR antagonist SR59230A on the tension and microRNA expression of rat thoracic aorta]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2017 Jan 8;33(1):6-10. Chinese. doi: 10.12047/j.cjap.5448.2017.002. PMID: 29926599.
In vitro protocol:
1. Pettersson US, Sandberg M, Jansson L. Two-week treatment with the β₃-adrenoceptor antagonist SR59230A normalizes the increased pancreatic islet blood flow in type 2 diabetic GK rats. Diabetes Obes Metab. 2012 Oct;14(10):960-2. doi: 10.1111/j.1463-1326.2012.01616.x. Epub 2012 May 28. PMID: 22564532.
2. Hutchinson DS, Sato M, Evans BA, Christopoulos A, Summers RJ. Evidence for pleiotropic signaling at the mouse beta3-adrenoceptor revealed by SR59230A [3-(2-Ethylphenoxy)-1-[(1,S)-1,2,3,4-tetrahydronapth-1-ylamino]-2S-2-propanol oxalate]. J Pharmacol Exp Ther. 2005 Mar;312(3):1064-74. doi: 10.1124/jpet.104.076901. Epub 2004 Dec 1. PMID: 15574684.
In vivo protocol:
1. Sun J, Cheng J, Ding X, Chi J, Yang J, Li W. β3 adrenergic receptor antagonist SR59230A exerts beneficial effects on right ventricular performance in monocrotaline-induced pulmonary arterial hypertension. Exp Ther Med. 2020 Jan;19(1):489-498. doi: 10.3892/etm.2019.8236. Epub 2019 Nov 22. PMID: 31853320; PMCID: PMC6909721.
2. Zhao QQ, Jing JN, Li HQ, Liu R, Li XP, Cui XL. [Effect of β3-AR antagonist SR59230A on the tension and microRNA expression of rat thoracic aorta]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2017 Jan 8;33(1):6-10. Chinese. doi: 10.12047/j.cjap.5448.2017.002. PMID: 29926599.
1: Jing JN, Li FL, Wang X, Wan X, Zhao QQ, Cui XL. [SR 59230A on the expression of MicroRNAs in myocardium of heart failure rats]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2017 May 8;33(5):456-460. Chinese. doi: 10.12047/j.cjap.5561.2017.109. PMID: 29926593.
2: Kulzer M, Seyler C, Welke F, Scherer D, Xynogalos P, Scholz EP, Thomas D, Becker R, Karle CA, Katus HA, Zitron E. Inhibition of cardiac Kir2.1-2.3 channels by beta3 adrenoreceptor antagonist SR 59230A. Biochem Biophys Res Commun. 2012 Jul 27;424(2):315-20. doi: 10.1016/j.bbrc.2012.06.114. Epub 2012 Jun 27. PMID: 22749993.
3: Pettersson US, Henriksnäs J, Jansson L. Reversal of high pancreatic islet and white adipose tissue blood flow in type 2 diabetic GK rats by administration of the beta3-adrenoceptor inhibitor SR-59230A. Am J Physiol Endocrinol Metab. 2009 Aug;297(2):E490-4. doi: 10.1152/ajpendo.00140.2009. Epub 2009 Jun 2. PMID: 19491297.
4: Leblais V, Pourageaud F, Ivorra MD, Guibert C, Marthan R, Muller B. Role of alpha-adrenergic receptors in the effect of the beta-adrenergic receptor ligands, CGP 12177, bupranolol, and SR 59230A, on the contraction of rat intrapulmonary artery. J Pharmacol Exp Ther. 2004 Apr;309(1):137-45. doi: 10.1124/jpet.103.061192. Epub 2004 Jan 12. PMID: 14718590.
5: MacDonald A, Watt K. Characterisation of the atypical beta-adrenoceptor in rabbit isolated jejunum using BRL 37344, cyanopindolol and SR 59230A. J Auton Pharmacol. 1999 Apr;19(2):91-5. doi: 10.1046/j.1365-2680.1999.00121.x. PMID: 10466941.
6: Dumas M, Dumas JP, Bardou M, Rochette L, Advenier C, Giudicelli JF. Influence of beta-adrenoceptor agonists on the pulmonary circulation. Effects of a beta3-adrenoceptor antagonist, SR 59230A. Eur J Pharmacol. 1998 May 8;348(2-3):223-8. doi: 10.1016/s0014-2999(98)00146-0. PMID: 9652337.
7: De Ponti F, Gibelli G, Croci T, Arcidiaco M, Crema F, Manara L. Functional evidence of atypical beta 3-adrenoceptors in the human colon using the beta 3-selective adrenoceptor antagonist, SR 59230A. Br J Pharmacol. 1996 Apr;117(7):1374-6. doi: 10.1111/j.1476-5381.1996.tb15294.x. PMID: 8730727; PMCID: PMC1909449.
8: Nisoli E, Tonello C, Landi M, Carruba MO. Functional studies of the first selective beta 3-adrenergic receptor antagonist SR 59230A in rat brown adipocytes. Mol Pharmacol. 1996 Jan;49(1):7-14. PMID: 8569714.
