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138908-40-4 | 1,3-Benzodioxole-2,2-dicarboxylic acid, 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-, sodium salt (1:2)
CAS No: 138908-40-4 Catalog No: AG001N3Y MDL No:
Product Description
Catalog Number:
AG001N3Y
Chemical Name:
1,3-Benzodioxole-2,2-dicarboxylic acid, 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-, sodium salt (1:2)
CAS Number:
138908-40-4
Molecular Formula:
C20H18ClNNa2O7
Molecular Weight:
465.7920
IUPAC Name:
disodium;5-[(2R)-2-[[(2R)-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/t11-,15+;;/m1../s1
InChI Key:
FUZBPOHHSBDTJQ-CFOQQKEYSA-L
SMILES:
C[C@H](Cc1ccc2c(c1)OC(O2)(C(=O)[O-])C(=O)[O-])NC[C@@H](c1cccc(c1)Cl)O.[Na+].[Na+]
UNII:
CF9MRO9QWW
Properties
Complexity:
578
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
465.057g/mol
Formal Charge:
0
Heavy Atom Count:
31
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
465.794g/mol
Monoisotopic Mass:
465.057g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
131A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Protective effects of the β3-adrenoceptor agonist CL316243 against N-methyl-D-aspartate-induced retinal neurotoxicity. | Naunyn-Schmiedeberg's archives of pharmacology 20121101 |
| Anatomical and functional assessment of brown adipose tissue by magnetic resonance imaging. | Obesity (Silver Spring, Md.) 20120701 |
| Interaction with caveolin-1 modulates G protein coupling of mouse β3-adrenoceptor. | The Journal of biological chemistry 20120608 |
| Increased thermogenic capacity of brown adipose tissue under low temperature and its contribution to arousal from hibernation in Syrian hamsters. | American journal of physiology. Regulatory, integrative and comparative physiology 20120101 |
| Effects and selectivity of CL 316243, beta-3-adrenoceptor agonist, in term-pregnant rat myometrium. | Gynecologic and obstetric investigation 20120101 |
| 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 20110501 |
| Brown adipose tissue responds to cold and adrenergic stimulation by induction of FGF21. | Molecular medicine (Cambridge, Mass.) 20110101 |
| β(3) adrenergic stimulation of the cardiac Na+-K+ pump by reversal of an inhibitory oxidative modification. | Circulation 20101221 |
| GPR40 is partially required for insulin secretion following activation of beta3-adrenergic receptors. | Molecular and cellular endocrinology 20100830 |
| Correlation between pharmacologically-induced changes in cystometric parameters and spinal c-Fos expression in rats. | Autonomic neuroscience : basic & clinical 20100825 |
| Differential involvement of caveolin-1 in brown adipocyte signaling: impaired beta3-adrenergic, but unaffected LPA, PDGF and EGF receptor signaling. | Biochimica et biophysica acta 20100801 |
| Pharmacological evidence for the presence of functional beta(3)-adrenoceptors in rat retinal blood vessels. | Naunyn-Schmiedeberg's archives of pharmacology 20100801 |
| Effects of CL316,243, a beta 3-adrenoceptor agonist, and intravesical prostaglandin E2 on the primary bladder afferent activity of the rat. | Neurourology and urodynamics 20100601 |
| The emergence of cold-induced brown adipocytes in mouse white fat depots is determined predominantly by white to brown adipocyte transdifferentiation. | American journal of physiology. Endocrinology and metabolism 20100601 |
| Beta(3)-adrenergic signaling acutely down regulates adipose triglyceride lipase in brown adipocytes. | Lipids 20100601 |
| Cyclooxygenase-2 controls energy homeostasis in mice by de novo recruitment of brown adipocytes. | Science (New York, N.Y.) 20100528 |
| Memory loss caused by beta-amyloid protein is rescued by a beta(3)-adrenoceptor agonist. | Neurobiology of aging 20100401 |
| Insulin-sensitizing therapy attenuates type 2 diabetes-mediated mammary tumor progression. | Diabetes 20100301 |
| Comparative effects of oleoyl-estrone and a specific beta3-adrenergic agonist (CL316, 243) on the expression of genes involved in energy metabolism of rat white adipose tissue. | Nutrition & metabolism 20100101 |
| Various emetogens increase the secretion of salivary amylase in rats: a potential model in emesis research. | Journal of pharmacological sciences 20100101 |
| Differential regulation of adipocyte PDE3B in distinct membrane compartments by insulin and the beta3-adrenergic receptor agonist CL316243: effects of caveolin-1 knockdown on formation/maintenance of macromolecular signalling complexes. | The Biochemical journal 20091210 |
| Spatiotemporal regulation of early lipolytic signaling in adipocytes. | The Journal of biological chemistry 20091113 |
| The stoichiometry of protein phosphorylation in adipocyte lipid droplets: analysis by N-terminal isotope tagging and enzymatic dephosphorylation. | Proteomics 20091101 |
| Effects of a novel beta(3)-adrenoceptor agonist, AJ-9677, on relaxation of the detrusor muscle: an in vitro study. | International journal of urology : official journal of the Japanese Urological Association 20081201 |
| Influence of potent and selective beta-adrenoceptor agonist, CL 316243, on the contractile response of non-pregnant human myometrium. | Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20081201 |
| Discovery of a novel series of benzoic acid derivatives as potent and selective human beta3 adrenergic receptor agonists with good oral bioavailability. 3. Phenylethanolaminotetraline (PEAT) skeleton containing biphenyl or biphenyl ether moiety. | Journal of medicinal chemistry 20080814 |
| 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. | The Journal of pharmacology and experimental therapeutics 20080701 |
| The effects of beta(3)-adrenoceptor agonist CL-316,243 on adiponectin, adiponectin receptors and tumor necrosis factor-alpha expressions in adipose tissues of obese diabetic KKAy mice. | European journal of pharmacology 20080414 |
| The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder. | European journal of pharmacology 20071114 |
| Beta2- and beta3-adrenoceptors activate glucose uptake in chick astrocytes by distinct mechanisms: a mechanism for memory enhancement? | Journal of neurochemistry 20071101 |
| Ligand-directed signaling at the beta3-adrenoceptor produced by 3-(2-Ethylphenoxy)-1-[(1,S)-1,2,3,4-tetrahydronapth-1-ylamino]-2S-2-propanol oxalate (SR59230A) relative to receptor agonists. | Molecular pharmacology 20071101 |
| Effect of the beta3 adrenoceptor agonist CL 316243 on hypothalamic 5-HT synthesis and suppression of REM sleep in the rat. | Journal of psychopharmacology (Oxford, England) 20070801 |
| An increase in murine skeletal muscle peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1alpha) mRNA in response to exercise is mediated by beta-adrenergic receptor activation. | Endocrinology 20070701 |
| Requirement of vimentin filament assembly for beta3-adrenergic receptor activation of ERK MAP kinase and lipolysis. | The Journal of biological chemistry 20070323 |
| Long-term regulation of cyclic nucleotide phosphodiesterase type 3B and 4 in 3T3-L1 adipocytes. | Biochemical and biophysical research communications 20070223 |
| Vagal afferents mediate the feeding response to mercaptoacetate but not to the beta (3) adrenergic receptor agonist CL 316,243. | Neuroscience letters 20070110 |
| Novel mechanisms of the regulation of protein kinase B in adipocytes; implications for protein kinase A, Epac, phosphodiesterases 3 and 4. | Cellular signalling 20070101 |
| Maximal beta3-adrenergic regulation of lipolysis involves Src and epidermal growth factor receptor-dependent ERK1/2 activation. | The Journal of biological chemistry 20061208 |
| Functional beta-adrenergic receptor signalling on nuclear membranes in adult rat and mouse ventricular cardiomyocytes. | Cardiovascular research 20060701 |
| Effect of adipocyte beta3-adrenergic receptor activation on the type 2 diabetic MKR mice. | American journal of physiology. Endocrinology and metabolism 20060601 |
| 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. | Journal of physiology and biochemistry 20060601 |
| 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. | Journal of physiology and biochemistry 20060601 |
| Leptin biosynthetic pathway in white adipocytes. | Biochemistry and cell biology = Biochimie et biologie cellulaire 20060401 |
| Role of PDE3B in insulin-induced glucose uptake, GLUT-4 translocation and lipogenesis in primary rat adipocytes. | Cellular signalling 20060301 |
| CL 316,243, a selective beta3-adrenergic agonist, inhibits protein breakdown in rat skeletal muscle. | Pflugers Archiv : European journal of physiology 20060201 |
| The full expression of fasting-induced torpor requires beta 3-adrenergic receptor signaling. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20060104 |
| Functional domains of the mouse beta3-adrenoceptor associated with differential G protein coupling. | The Journal of pharmacology and experimental therapeutics 20051201 |
| Direct demonstration of beta1- and evidence against beta2- and beta3-adrenoceptors, in smooth muscle cells of rat small mesenteric arteries. | British journal of pharmacology 20051101 |
| Relaxant effects of beta-adrenergic agonists on porcine and human detrusor muscle. | Acta physiologica Scandinavica 20051001 |
| Combined effects of oleoyl-estrone and a beta3-adrenergic agonist (CL316,243) on lipid stores of diet-induced overweight male Wistar rats. | Life sciences 20050902 |
| The beta3-adrenergic agonist CL316,243 inhibits insulin signaling but not glucose uptake in primary human adipocytes. | Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20050901 |
| Adiponectin receptor 2 expression in liver and insulin resistance in db/db mice given a beta3-adrenoceptor agonist. | European journal of pharmacology 20050725 |
| Inhibition of ultrasonic vocalizations by beta-adrenoceptor agonists. | Developmental psychobiology 20050701 |
| Comparison of the alpha-adrenoceptor-mediated effects of beta3-adrenoceptor ligands in rat pulmonary artery. | Naunyn-Schmiedeberg's archives of pharmacology 20050601 |
| A search for presynaptic beta3-adrenoceptors in the rat. | Fundamental & clinical pharmacology 20050401 |
| 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]. | The Journal of pharmacology and experimental therapeutics 20050301 |
| The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors. | British journal of pharmacology 20050201 |
| Potential role for nonesterified fatty acids in beta-adrenoceptor-induced increases in brain tryptophan. | Neurochemistry international 20050101 |
| Effect of a beta-3 agonist on food intake in two strains of rats that differ in susceptibility to obesity. | Physiology & behavior 20040915 |
| Contributions of dysregulated energy metabolism to type 2 diabetes development in NZO/H1Lt mice with polygenic obesity. | Metabolism: clinical and experimental 20040601 |
| White adipose tissue contributes to UCP1-independent thermogenesis. | American journal of physiology. Endocrinology and metabolism 20031201 |
| Role of nitric oxide in beta3-adrenoceptor activation on basal tone of internal anal sphincter. | American journal of physiology. Gastrointestinal and liver physiology 20030901 |
| Functional characterization of beta-adrenoceptor subtypes in the canine and rat lower urinary tract. | The Journal of urology 20030801 |
| beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor. | Cardiovascular research 20030801 |
| Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter. | Pharmacology 20030701 |
| Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system. | American journal of physiology. Regulatory, integrative and comparative physiology 20030601 |
| Inhibitory effect of beta3-adrenoceptor agonist in lower esophageal sphincter smooth muscle: in vitro studies. | The Journal of pharmacology and experimental therapeutics 20030101 |
| New series of N-substituted phenyl ketone oxime ethers: synthesis and bovine beta3-adrenergic agonistic activities. | Die Pharmazie 20030101 |
| Beta3 adrenergic stimulation inhibits the opossum lower esophageal sphincter. | Gastroenterology 20021101 |
| Regulation of adiponectin and leptin gene expression in white and brown adipose tissues: influence of beta3-adrenergic agonists, retinoic acid, leptin and fasting. | Biochimica et biophysica acta 20021010 |
| Effects of selective beta2 and beta3-adrenoceptor agonists on detrusor hyperreflexia in conscious cerebral infarcted rats. | The Journal of urology 20020901 |
| (123)I- or (125)I-metaiodobenzylguanidine visualization of brown adipose tissue. | Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20020901 |
| beta(3)-Adrenoceptor agonists: potential, pitfalls and progress. | European journal of pharmacology 20020412 |
| Mouse beta 3a- and beta 3b-adrenoceptors expressed in Chinese hamster ovary cells display identical pharmacology but utilize distinct signalling pathways. | British journal of pharmacology 20020401 |
| Modification of ureteral motility and promotion of urine flow around an intraureteral obstruction by CL-316243, phenylephrine, and furosemide in dogs. | Neurourology and urodynamics 20020101 |
| Effects of beta(3)-adrenoceptor stimulation on prostaglandin E(2)-induced bladder hyperactivity and on the cardiovascular system in conscious rats. | Neurourology and urodynamics 20020101 |
| beta-3 adrenergic agonist restores skeletal muscle insulin responsiveness in Sprague-Dawley rats. | Biochemical and biophysical research communications 20011221 |
| Beta 3 agonists. Part 1: evolution from inception to BMS-194449. | Bioorganic & medicinal chemistry letters 20011203 |
| beta-Adrenergic regulation of IL-6 release from adipose tissue: in vivo and in vitro studies. | The Journal of clinical endocrinology and metabolism 20011201 |
| The type 2 iodothyronine deiodinase is essential for adaptive thermogenesis in brown adipose tissue. | The Journal of clinical investigation 20011101 |
| Pancreatic beta-cells expressing the Arg64 variant of the beta(3)-adrenergic receptor exhibit abnormal insulin secretory activity. | Journal of molecular endocrinology 20011001 |
| Efficacy of the beta3-adrenergic receptor agonist CL-316243 on experimental bladder hyperreflexia and detrusor instability in the rat. | The Journal of urology 20010901 |
| 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: clinical and experimental 20010801 |
| beta-Adrenergic activation of p38 MAP kinase in adipocytes: cAMP induction of the uncoupling protein 1 (UCP1) gene requires p38 MAP kinase. | The Journal of biological chemistry 20010720 |
| Effect of the beta(3)-adrenergic agonist Cl316,243 on functional differentiation of white and brown adipocytes in primary cell culture. | Biochimica et biophysica acta 20010528 |
| Discovery of novel N-phenylglycine derivatives as potent and selective beta(3)-adrenoceptor agonists for the treatment of frequent urination and urinary incontinence. | Journal of medicinal chemistry 20010426 |
| (4-Piperidin-1-yl)phenyl amides: potent and selective human beta(3) agonists. | Journal of medicinal chemistry 20010426 |
| 2,4-Thiazolidinediones as potent and selective human beta3 agonists. | Bioorganic & medicinal chemistry letters 20010326 |
| beta(1)- and beta(3)-adrenoceptor mediated smooth muscle relaxation in hypothyroid rat ileum. | European journal of pharmacology 20010301 |
| Beta 3-adrenergic agonist up-regulates uncoupling proteins 2 and 3 in skeletal muscle of the mouse. | The Journal of veterinary medical science 20010301 |
| CCAAT/enhancer-binding protein alpha is required for transcription of the beta 3-adrenergic receptor gene during adipogenesis. | The Journal of biological chemistry 20010105 |
| beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice. | British journal of pharmacology 20010101 |
| Selectivity and potency of agonists for the three subtypes of cloned human beta-adrenoceptors expressed in Chinese hamster ovary cells. | The Tohoku journal of experimental medicine 20001101 |
| beta(3)-adrenoceptor regulation and relaxation responses in mouse ileum. | British journal of pharmacology 20000301 |
| Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells. | Naunyn-Schmiedeberg's archives of pharmacology 19990401 |
| Is the 'atypical' beta-receptor in the rat stomach fundus the rat beta 3 receptor? | The Journal of pharmacology and experimental therapeutics 19950101 |
| Penicillin derived C2-symmetric dimers as novel inhibitors of HIV-1 proteinase. | Journal of medicinal chemistry 19920807 |
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