CL 316243 disodium salt

• CAT Number: I013984
• CAS Number: 151126-84-0
• Molecular Formula: C20H18ClNNa2O7
• Molecular Weight: 465.8
• Purity: ≥95%
• Target: Adrenergic Receptor
• Solubility: Soluble to 100 mM in sterile water
• Storage: Desiccate at -20C
• IUPAC Name: disodium;5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate
• InChI: InChI=1S/C20H20ClNO7.2Na/c1-11(22-10-15(23)13-3-2-4-14(21)9-13)7-12-5-6-16-17(8-12)29-20(28-16,18(24)25)19(26)27;;/h2-6,8-9,11,15,22-23H,7,10H2,1H3,(H,24,25)(H,26,27);;/q;2*+1/p-2
• InChIKey: FUZBPOHHSBDTJQ-UHFFFAOYSA-L
• SMILES: CC(CC1=CC2=C(C=C1)OC(O2)(C(=O)[O-])C(=O)[O-])NCC(C3=CC(=CC=C3)Cl)O.[Na+].[Na+]

CL 316243 disodium salt(151126-84-0) is a potent and highly selective β3-adrenoceptor agonist (EC50 = 3 nM); > 10000-fold selective over β1 and β2 receptors. Increases brown adipose tissue thermogenesis and metabolic rate, and decreases blood insulin and glucose levels following oral administration in vivo.

Reference

1: Kaya T, Karadas B, Altun A, Sarac İ, Bagcivan I. Effects and selectivity of CL 316243, beta-3-adrenoceptor agonist, in term-pregnant rat myometrium. Gynecol Obstet Invest. 2012;73(1):63-9. doi: 10.1159/000332393. Epub 2011 Dec 22. PubMed PMID: 22189156.
2: Wanajo I, Tomiyama Y, Yamazaki Y, Kojima M. Ureteral selectivity of intravenous β-adrenoceptor agonists in pig model of acute ureteral obstruction: comparison of KUL-7211, a selective β2/β3 agonist, with isoproterenol, terbutaline, and CL-316243. Urology. 2011 May;77(5):1266.e1-6. doi: 10.1016/j.urology.2010.12.045. Epub 2011 Mar 12. PubMed PMID: 21397304.
3: Pedzinska-Betiuk A, Modzelewska B, Kostrzewska A, Jozwik M. Influence of potent and selective beta-adrenoceptor agonist, CL 316243, on the contractile response of non-pregnant human myometrium. J Physiol Pharmacol. 2008 Dec;59 Suppl 9:43-54. PubMed PMID: 19261970.
4: Leon LA, Hoffman BE, Gardner SD, Laping NJ, Evans C, Lashinger ES, Su X. Effects of the beta 3-adrenergic receptor agonist disodium 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole -2,2-dicarboxylate (CL-316243) on bladder micturition reflex in spontaneously hypertensive rats. J Pharmacol Exp Ther. 2008 Jul;326(1):178-85. doi: 10.1124/jpet.108.138651. Epub 2008 Apr 15. PubMed PMID: 18413856.
5: Conley RK, Li J, Ivarsson M, Hutson PH. Effect of the beta3 adrenoceptor agonist CL 316243 on hypothalamic 5-HT synthesis and suppression of REM sleep in the rat. J Psychopharmacol. 2007 Aug;21(6):597-602. Epub 2006 Nov 8. PubMed PMID: 17092981.
6: Duffaut C, Bour S, Prévot D, Marti L, Testar X, Zorzano A, Carpéné C. Prolonged treatment with the beta3-adrenergic agonist CL 316243 induces adipose tissue remodeling in rat but not in guinea pig: 2) modulation of glucose uptake and monoamine oxidase activity. J Physiol Biochem. 2006 Jun;62(2):101-11. PubMed PMID: 17217164.
7: Ferrand C, Redonnet A, Prévot D, Carpéné C, Atgié C. Prolonged treatment with the beta3-adrenergic agonist CL 316243 induces adipose tissue remodeling in rat but not in guinea pig: 1) fat store depletion and desensitization of beta-adrenergic responses. J Physiol Biochem. 2006 Jun;62(2):89-99. PubMed PMID: 17217163.
8: Tomiyama Y, Murakami M, Yamazaki Y, Kojima M, Akahane M. Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter. Pharmacology. 2003 Jul;68(3):140-6. PubMed PMID: 12784085.
9: Tomiyama Y, Murakami M, Akiyama K, Kojima M, Akahane M, Park YC, Kurita T. Modification of ureteral motility and promotion of urine flow around an intraureteral obstruction by CL-316243, phenylephrine, and furosemide in dogs. Neurourol Urodyn. 2002;21(3):251-7. PubMed PMID: 11948718.
10: Woods M, Carson N, Norton NW, Sheldon JH, Argentieri TM. Efficacy of the beta3-adrenergic receptor agonist CL-316243 on experimental bladder hyperreflexia and detrusor instability in the rat. J Urol. 2001 Sep;166(3):1142-7. PubMed PMID: 11490313.
11: Blachère JC, Pérusse F, Bukowiecki LJ. Lowering plasma free fatty acids with Acipimox mimics the antidiabetic effects of the beta 3-adrenergic agonist CL-316243 in obese Zucker diabetic fatty rats. Metabolism. 2001 Aug;50(8):945-51. PubMed PMID: 11474483.
12: Himms-Hagen J, Melnyk A, Zingaretti MC, Ceresi E, Barbatelli G, Cinti S. Multilocular fat cells in WAT of CL-316243-treated rats derive directly from white adipocytes. Am J Physiol Cell Physiol. 2000 Sep;279(3):C670-81. PubMed PMID: 10942717.
13: Castillo-Meléndez M, McKinley MJ, Summers RJ. Intracerebroventricular administration of the beta(3)-adrenoceptor agonist CL 316243 causes Fos immunoreactivity in discrete regions of rat hypothalamus. Neurosci Lett. 2000 Sep 1;290(3):161-4. PubMed PMID: 10963888.
14: Liu X, Pérusse F, Bukowiecki LJ. Mechanisms of the antidiabetic effects of the beta 3-adrenergic agonist CL-316243 in obese Zucker-ZDF rats. Am J Physiol. 1998 May;274(5 Pt 2):R1212-9. PubMed PMID: 9644032.