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138908-40-4,MFCD19053158
Catalog No.:AA001N16

138908-40-4 | CL316243 Disodium Salt

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1mg
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5mg
≥95%
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10mg
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA001N16
Chemical Name:
CL316243 Disodium Salt
CAS Number:
138908-40-4
Molecular Formula:
C20H18ClNNa2O7
Molecular Weight:
465.7920
MDL Number:
MFCD19053158
SMILES:
C[C@H](Cc1ccc2c(c1)OC(O2)(C(=O)[O-])C(=O)[O-])NC[C@@H](c1cccc(c1)Cl)O.[Na+].[Na+]
Properties
Computed Properties
 
Complexity:
578  
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
6  

Literature

Title: Protective effects of the β3-adrenoceptor agonist CL316243 against N-methyl-D-aspartate-induced retinal neurotoxicity.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20121101

Title: Anatomical and functional assessment of brown adipose tissue by magnetic resonance imaging.

Journal: Obesity (Silver Spring, Md.) 20120701

Title: Interaction with caveolin-1 modulates G protein coupling of mouse β3-adrenoceptor.

Journal: The Journal of biological chemistry 20120608

Title: Increased thermogenic capacity of brown adipose tissue under low temperature and its contribution to arousal from hibernation in Syrian hamsters.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20120101

Title: Effects and selectivity of CL 316243, beta-3-adrenoceptor agonist, in term-pregnant rat myometrium.

Journal: Gynecologic and obstetric investigation 20120101

Title: 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.

Journal: Urology 20110501

Title: Brown adipose tissue responds to cold and adrenergic stimulation by induction of FGF21.

Journal: Molecular medicine (Cambridge, Mass.) 20110101

Title: β(3) adrenergic stimulation of the cardiac Na+-K+ pump by reversal of an inhibitory oxidative modification.

Journal: Circulation 20101221

Title: GPR40 is partially required for insulin secretion following activation of beta3-adrenergic receptors.

Journal: Molecular and cellular endocrinology 20100830

Title: Correlation between pharmacologically-induced changes in cystometric parameters and spinal c-Fos expression in rats.

Journal: Autonomic neuroscience : basic & clinical 20100825

Title: Differential involvement of caveolin-1 in brown adipocyte signaling: impaired beta3-adrenergic, but unaffected LPA, PDGF and EGF receptor signaling.

Journal: Biochimica et biophysica acta 20100801

Title: Pharmacological evidence for the presence of functional beta(3)-adrenoceptors in rat retinal blood vessels.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20100801

Title: Effects of CL316,243, a beta 3-adrenoceptor agonist, and intravesical prostaglandin E2 on the primary bladder afferent activity of the rat.

Journal: Neurourology and urodynamics 20100601

Title: The emergence of cold-induced brown adipocytes in mouse white fat depots is determined predominantly by white to brown adipocyte transdifferentiation.

Journal: American journal of physiology. Endocrinology and metabolism 20100601

Title: Beta(3)-adrenergic signaling acutely down regulates adipose triglyceride lipase in brown adipocytes.

Journal: Lipids 20100601

Title: Cyclooxygenase-2 controls energy homeostasis in mice by de novo recruitment of brown adipocytes.

Journal: Science (New York, N.Y.) 20100528

Title: Memory loss caused by beta-amyloid protein is rescued by a beta(3)-adrenoceptor agonist.

Journal: Neurobiology of aging 20100401

Title: Insulin-sensitizing therapy attenuates type 2 diabetes-mediated mammary tumor progression.

Journal: Diabetes 20100301

Title: 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.

Journal: Nutrition & metabolism 20100101

Title: Various emetogens increase the secretion of salivary amylase in rats: a potential model in emesis research.

Journal: Journal of pharmacological sciences 20100101

Title: 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.

Journal: The Biochemical journal 20091210

Title: Spatiotemporal regulation of early lipolytic signaling in adipocytes.

Journal: The Journal of biological chemistry 20091113

Title: The stoichiometry of protein phosphorylation in adipocyte lipid droplets: analysis by N-terminal isotope tagging and enzymatic dephosphorylation.

Journal: Proteomics 20091101

Title: Effects of a novel beta(3)-adrenoceptor agonist, AJ-9677, on relaxation of the detrusor muscle: an in vitro study.

Journal: International journal of urology : official journal of the Japanese Urological Association 20081201

Title: Influence of potent and selective beta-adrenoceptor agonist, CL 316243, on the contractile response of non-pregnant human myometrium.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20081201

Title: 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: Journal of medicinal chemistry 20080814

Title: 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.

Journal: The Journal of pharmacology and experimental therapeutics 20080701

Title: 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.

Journal: European journal of pharmacology 20080414

Title: The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.

Journal: European journal of pharmacology 20071114

Title: Beta2- and beta3-adrenoceptors activate glucose uptake in chick astrocytes by distinct mechanisms: a mechanism for memory enhancement?

Journal: Journal of neurochemistry 20071101

Title: 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.

Journal: Molecular pharmacology 20071101

Title: Effect of the beta3 adrenoceptor agonist CL 316243 on hypothalamic 5-HT synthesis and suppression of REM sleep in the rat.

Journal: Journal of psychopharmacology (Oxford, England) 20070801

Title: 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.

Journal: Endocrinology 20070701

Title: Requirement of vimentin filament assembly for beta3-adrenergic receptor activation of ERK MAP kinase and lipolysis.

Journal: The Journal of biological chemistry 20070323

Title: Long-term regulation of cyclic nucleotide phosphodiesterase type 3B and 4 in 3T3-L1 adipocytes.

Journal: Biochemical and biophysical research communications 20070223

Title: Vagal afferents mediate the feeding response to mercaptoacetate but not to the beta (3) adrenergic receptor agonist CL 316,243.

Journal: Neuroscience letters 20070110

Title: Novel mechanisms of the regulation of protein kinase B in adipocytes; implications for protein kinase A, Epac, phosphodiesterases 3 and 4.

Journal: Cellular signalling 20070101

Title: Maximal beta3-adrenergic regulation of lipolysis involves Src and epidermal growth factor receptor-dependent ERK1/2 activation.

Journal: The Journal of biological chemistry 20061208

Title: Functional beta-adrenergic receptor signalling on nuclear membranes in adult rat and mouse ventricular cardiomyocytes.

Journal: Cardiovascular research 20060701

Title: Effect of adipocyte beta3-adrenergic receptor activation on the type 2 diabetic MKR mice.

Journal: American journal of physiology. Endocrinology and metabolism 20060601

Title: 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: Journal of physiology and biochemistry 20060601

Title: 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: Journal of physiology and biochemistry 20060601

Title: Leptin biosynthetic pathway in white adipocytes.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20060401

Title: Role of PDE3B in insulin-induced glucose uptake, GLUT-4 translocation and lipogenesis in primary rat adipocytes.

Journal: Cellular signalling 20060301

Title: CL 316,243, a selective beta3-adrenergic agonist, inhibits protein breakdown in rat skeletal muscle.

Journal: Pflugers Archiv : European journal of physiology 20060201

Title: The full expression of fasting-induced torpor requires beta 3-adrenergic receptor signaling.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20060104

Title: Functional domains of the mouse beta3-adrenoceptor associated with differential G protein coupling.

Journal: The Journal of pharmacology and experimental therapeutics 20051201

Title: Direct demonstration of beta1- and evidence against beta2- and beta3-adrenoceptors, in smooth muscle cells of rat small mesenteric arteries.

Journal: British journal of pharmacology 20051101

Title: Relaxant effects of beta-adrenergic agonists on porcine and human detrusor muscle.

Journal: Acta physiologica Scandinavica 20051001

Title: Combined effects of oleoyl-estrone and a beta3-adrenergic agonist (CL316,243) on lipid stores of diet-induced overweight male Wistar rats.

Journal: Life sciences 20050902

Title: The beta3-adrenergic agonist CL316,243 inhibits insulin signaling but not glucose uptake in primary human adipocytes.

Journal: Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20050901

Title: Adiponectin receptor 2 expression in liver and insulin resistance in db/db mice given a beta3-adrenoceptor agonist.

Journal: European journal of pharmacology 20050725

Title: Inhibition of ultrasonic vocalizations by beta-adrenoceptor agonists.

Journal: Developmental psychobiology 20050701

Title: Comparison of the alpha-adrenoceptor-mediated effects of beta3-adrenoceptor ligands in rat pulmonary artery.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20050601

Title: A search for presynaptic beta3-adrenoceptors in the rat.

Journal: Fundamental & clinical pharmacology 20050401

Title: 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].

Journal: The Journal of pharmacology and experimental therapeutics 20050301

Title: The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.

Journal: British journal of pharmacology 20050201

Title: Potential role for nonesterified fatty acids in beta-adrenoceptor-induced increases in brain tryptophan.

Journal: Neurochemistry international 20050101

Title: Effect of a beta-3 agonist on food intake in two strains of rats that differ in susceptibility to obesity.

Journal: Physiology & behavior 20040915

Title: Contributions of dysregulated energy metabolism to type 2 diabetes development in NZO/H1Lt mice with polygenic obesity.

Journal: Metabolism: clinical and experimental 20040601

Title: White adipose tissue contributes to UCP1-independent thermogenesis.

Journal: American journal of physiology. Endocrinology and metabolism 20031201

Title: Role of nitric oxide in beta3-adrenoceptor activation on basal tone of internal anal sphincter.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20030901

Title: Functional characterization of beta-adrenoceptor subtypes in the canine and rat lower urinary tract.

Journal: The Journal of urology 20030801

Title: beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor.

Journal: Cardiovascular research 20030801

Title: Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter.

Journal: Pharmacology 20030701

Title: Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20030601

Title: Inhibitory effect of beta3-adrenoceptor agonist in lower esophageal sphincter smooth muscle: in vitro studies.

Journal: The Journal of pharmacology and experimental therapeutics 20030101

Title: New series of N-substituted phenyl ketone oxime ethers: synthesis and bovine beta3-adrenergic agonistic activities.

Journal: Die Pharmazie 20030101

Title: Beta3 adrenergic stimulation inhibits the opossum lower esophageal sphincter.

Journal: Gastroenterology 20021101

Title: Regulation of adiponectin and leptin gene expression in white and brown adipose tissues: influence of beta3-adrenergic agonists, retinoic acid, leptin and fasting.

Journal: Biochimica et biophysica acta 20021010

Title: Effects of selective beta2 and beta3-adrenoceptor agonists on detrusor hyperreflexia in conscious cerebral infarcted rats.

Journal: The Journal of urology 20020901

Title: (123)I- or (125)I-metaiodobenzylguanidine visualization of brown adipose tissue.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20020901

Title: beta(3)-Adrenoceptor agonists: potential, pitfalls and progress.

Journal: European journal of pharmacology 20020412

Title: Mouse beta 3a- and beta 3b-adrenoceptors expressed in Chinese hamster ovary cells display identical pharmacology but utilize distinct signalling pathways.

Journal: British journal of pharmacology 20020401

Title: Modification of ureteral motility and promotion of urine flow around an intraureteral obstruction by CL-316243, phenylephrine, and furosemide in dogs.

Journal: Neurourology and urodynamics 20020101

Title: Effects of beta(3)-adrenoceptor stimulation on prostaglandin E(2)-induced bladder hyperactivity and on the cardiovascular system in conscious rats.

Journal: Neurourology and urodynamics 20020101

Title: beta-3 adrenergic agonist restores skeletal muscle insulin responsiveness in Sprague-Dawley rats.

Journal: Biochemical and biophysical research communications 20011221

Title: Beta 3 agonists. Part 1: evolution from inception to BMS-194449.

Journal: Bioorganic & medicinal chemistry letters 20011203

Title: beta-Adrenergic regulation of IL-6 release from adipose tissue: in vivo and in vitro studies.

Journal: The Journal of clinical endocrinology and metabolism 20011201

Title: The type 2 iodothyronine deiodinase is essential for adaptive thermogenesis in brown adipose tissue.

Journal: The Journal of clinical investigation 20011101

Title: Pancreatic beta-cells expressing the Arg64 variant of the beta(3)-adrenergic receptor exhibit abnormal insulin secretory activity.

Journal: Journal of molecular endocrinology 20011001

Title: Efficacy of the beta3-adrenergic receptor agonist CL-316243 on experimental bladder hyperreflexia and detrusor instability in the rat.

Journal: The Journal of urology 20010901

Title: 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.

Journal: Metabolism: clinical and experimental 20010801

Title: beta-Adrenergic activation of p38 MAP kinase in adipocytes: cAMP induction of the uncoupling protein 1 (UCP1) gene requires p38 MAP kinase.

Journal: The Journal of biological chemistry 20010720

Title: Effect of the beta(3)-adrenergic agonist Cl316,243 on functional differentiation of white and brown adipocytes in primary cell culture.

Journal: Biochimica et biophysica acta 20010528

Title: Discovery of novel N-phenylglycine derivatives as potent and selective beta(3)-adrenoceptor agonists for the treatment of frequent urination and urinary incontinence.

Journal: Journal of medicinal chemistry 20010426

Title: (4-Piperidin-1-yl)phenyl amides: potent and selective human beta(3) agonists.

Journal: Journal of medicinal chemistry 20010426

Title: 2,4-Thiazolidinediones as potent and selective human beta3 agonists.

Journal: Bioorganic & medicinal chemistry letters 20010326

Title: beta(1)- and beta(3)-adrenoceptor mediated smooth muscle relaxation in hypothyroid rat ileum.

Journal: European journal of pharmacology 20010301

Title: Beta 3-adrenergic agonist up-regulates uncoupling proteins 2 and 3 in skeletal muscle of the mouse.

Journal: The Journal of veterinary medical science 20010301

Title: CCAAT/enhancer-binding protein alpha is required for transcription of the beta 3-adrenergic receptor gene during adipogenesis.

Journal: The Journal of biological chemistry 20010105

Title: beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.

Journal: British journal of pharmacology 20010101

Title: Selectivity and potency of agonists for the three subtypes of cloned human beta-adrenoceptors expressed in Chinese hamster ovary cells.

Journal: The Tohoku journal of experimental medicine 20001101

Title: beta(3)-adrenoceptor regulation and relaxation responses in mouse ileum.

Journal: British journal of pharmacology 20000301

Title: Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19990401

Title: Is the 'atypical' beta-receptor in the rat stomach fundus the rat beta 3 receptor?

Journal: The Journal of pharmacology and experimental therapeutics 19950101

Title: Penicillin derived C2-symmetric dimers as novel inhibitors of HIV-1 proteinase.

Journal: Journal of medicinal chemistry 19920807

Title: Bloom JD, et al. Disodium (R,R)-5--[-(3-chlorophenyl)-2-hydroxyethyl-amino propyl-1,3-benzodioxole-2,2-dicarboxylate (CL 316,243). A potent beta-adrenergic agonist virtually specific for beta 3 receptors. A promising antidiabetic and antiobesity agent.J Med Chem. 1992 Aug 7;35(16):3081-4.

Title: Shin W, et al. Impaired adrenergic agonist-dependent beige adipocyte induction in obese mice.J Vet Med Sci. 2019 Jun 6;81(6):799-807.

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Tags:138908-40-4 Molecular Formula|138908-40-4 MDL|138908-40-4 SMILES|138908-40-4 CL316243 Disodium Salt