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C5976

Sigma-Aldrich

CL 316,243 hydrate

≥98% (HPLC), powder

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Synonym(s):
Disodium 5-[(2R)-2-[[(2R)-2-(3-Chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate hydrate
Empirical Formula (Hill Notation):
C20H18ClNNa2O7 · xH2O
CAS Number:
138908-40-4
Molecular Weight:
465.79 (anhydrous basis)
MDL number:
MFCD19053158
UNSPSC Code:
12352200
PubChem Substance ID:
24278325
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 10 mg/mL, clear

originator

Wyeth

storage temp.

room temp

SMILES string

O.[Na+].[Na+].C[C@H](Cc1ccc2OC(Oc2c1)(C([O-])=O)C([O-])=O)NC[C@H](O)c3cccc(Cl)c3

InChI

1S/C20H20ClNO7.2Na.H2O/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);;;1H2/q;2*+1;/p-2/t11-,15+;;;/m1.../s1

InChI key

BFEWLXURNRQQLY-BELDDISZSA-L

Gene Information

human ... ADRB3(155)

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Application

CL 316,243 hydrate has been used:
  • as a β-agonists to inject mice and study its effect on the expression of mammalian major facilitator superfamily domain-containing protein (Mfsd2a)
  • as an adrenergic agonist to stimulate adrenergic response in order to study the metabolic activity of brown, beige and white adipose tissues in mice
  • as a β3-adrenergic agonist to inject mice for in vivo lipolytic challenge

Biochem/physiol Actions

β Adrenoceptor is expressed in a number of tissues such as heart, adipose tissue, colon and other tissues. It is associated with many different biological functions. β Adrenoceptor fills in as an objective for treating type 2 diabetes, heart failure, cachexia, obesity, metabolic disorder, issues related with bladder, colon and malignant tumor growth. Depression and anxiety can also be treated via β adrenoceptor. CL 316,243 is known to have antidiabetic action via β adrenoceptor. It is a potent stimulator of lipolysis. It also activates β3- adrenoceptors on neurons in hypothalamic areas that are important in the central regulation of appetite.
CL 316,243 is a β3 adrenoceptor agonist; anti-obesity agent.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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 Wyeth. 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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beta3-Adrenoceptor agonists and (antagonists as) inverse agonists: history, perspective, constitutive activity, and stereospecific binding
Methods in Enzymology, 484, 197-230 (2010)
Intracerebroventricular administration of the beta3-adrenoceptor agonist CL 316243 causes Fos immunoreactivity in discrete regions of rat hypothalamus
Castillo-Melendez M, et al.
Neuroscience Letters, 290(3), 161-164 (2000)
Mfsd2a encodes a novel major facilitator superfamily domain-containing protein highly induced in brown adipose tissue during fasting and adaptive thermogenesis
Angers M, et al.
The Biochemical Journal, 416(3), 347-355 (2008)
Metabolic activity of brown,?beige,? and white adipose tissues in response to chronic adrenergic stimulation in male mice
Labbe SM, et al.
American Journal of Physiology. Endocrinology and Metabolism, 311(1), E260-E268 (2016)
Y Igawa et al.
British journal of pharmacology, 126(3), 819-825 (1999-04-03)
The possible existence of a beta3-adrenergic receptor (beta3-AR) in the human detrusor muscle was investigated by in vitro functional studies and analysis of mRNA expression. Isoprenaline, noradrenaline and adrenaline each produced a concentration-dependent relaxation of the human detrusor. The rank
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