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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H20ClNO7
Molecular Weight 421.828
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CL-316243 FREE DIACID

SMILES

C[C@H](CC1=CC=C2OC(OC2=C1)(C(O)=O)C(O)=O)NC[C@H](O)C3=CC(Cl)=CC=C3

InChI

InChIKey=JEDJMKTVUPSHFW-ABAIWWIYSA-N
InChI=1S/C20H20ClNO7/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)/t11-,15+/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H20ClNO7
Molecular Weight 421.828
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21170122 | https://www.ncbi.nlm.nih.gov/pubmed/11311069 | https://www.ncbi.nlm.nih.gov/pubmed/26988163

CL-316243 is a selective and highly specific β3-adrenoceptor agonist. CL 316243 possesses anti-obesity and anti-diabetic effects due to increasing brown adipose tissue thermogenesis and metabolic rate, and consequently may be useful for treating obesity as well as non-insulin-dependent diabetes mellitus in obese persons, without causing excessive side effects.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
220.0 nM [EC50]
262.0 µM [EC50]
111.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Is the "atypical" beta-receptor in the rat stomach fundus the rat beta 3 receptor?
1995 Jan
The full expression of fasting-induced torpor requires beta 3-adrenergic receptor signaling.
2006 Jan 4
The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.
2007 Nov 14
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.
2010 Feb 25
Patents

Patents

Sample Use Guides

The daily dose for rats was 1 mg/ kg body weight for 4 weeks
Route of Administration: Oral
Effect of CL (CL-316243) alone or in combination with ADA, PTX or WT on PI(3,4,5)P3 production were studied using rat epididymal adipocytes. [32P]orthophosphate-labeled adipocytes that were treated or not treated with ADA (2 U/ml, 10 min) or PTX (1 μg/ml, 60 min) were incubated for 1 min with or without CL (1 μM). In addition, [32P]orthophosphate-labeled adipocytes treated with or without WT (3 μM, 1 min) were incubated for 1 min with or without CL or INS (0.7 μM). Furthermore, adipocytes treated or not treated with ADA or PTX were incubated for 10 min with or without CL. The radioactivity of PI(3,4,5)P3 (PIP3) that were separated by TLC and the accumulation of cAMP in adipocytes were determined.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:22:03 GMT 2023
Edited
by admin
on Sat Dec 16 10:22:03 GMT 2023
Record UNII
52H8DB0TKX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CL-316243 FREE DIACID
Common Name English
5-((2R)-2-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)-1,3-BENZODIOXOLE-2,2-DICARBOXYLIC ACID
Systematic Name English
1,3-BENZODIOXOLE-2,2-DICARBOXYLIC ACID, 5-((2R)-2-(((2R)-2-(3-CHLOROPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)-
Systematic Name English
Code System Code Type Description
FDA UNII
52H8DB0TKX
Created by admin on Sat Dec 16 10:22:04 GMT 2023 , Edited by admin on Sat Dec 16 10:22:04 GMT 2023
PRIMARY
PUBCHEM
5486546
Created by admin on Sat Dec 16 10:22:04 GMT 2023 , Edited by admin on Sat Dec 16 10:22:04 GMT 2023
PRIMARY
CAS
183720-02-7
Created by admin on Sat Dec 16 10:22:04 GMT 2023 , Edited by admin on Sat Dec 16 10:22:04 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY