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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO
Molecular Weight 383.5253
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRECADRINE

SMILES

C[C@@H]([C@H](O)C1=CC=CC=C1)N(C)CC=C2C3=C(CCC4=C2C=CC=C4)C=CC=C3

InChI

InChIKey=BHVGOYREXHCFOE-DCFHFQCYSA-N
InChI=1S/C27H29NO/c1-20(27(29)23-12-4-3-5-13-23)28(2)19-18-26-24-14-8-6-10-21(24)16-17-22-11-7-9-15-25(22)26/h3-15,18,20,27,29H,16-17,19H2,1-2H3/t20-,27-/m0/s1

HIDE SMILES / InChI
Trecadrine is a beta3-adrenergic agonist. Trecadrine could have normalized the oxygen consumption by the liver, in which other metabolic pathways could be involved. The administration of Trecadrine produced a statistically significant decrease in glucose levels, which is not related to changes in insulin levels. Trecadrine administration to animals significantly inhibited galactose intestinal absorption, which was independently confirmed by additional in-vitro studies and decreased disaccharidase activities. Trecadrine enhance glucose storage in liver, probably through a non-insulin dependent mechanism of action. Trecadrine administration may have a therapeutic potential in disorders associated with hypertriglyceridemia such as obesity and some types of hyperlipidaemias. Trecadrine shows a potent hypoglycaemic effect in the alloxan-induced model of diabetes in rats by decreasing hepatic glucose output and improving muscle glucose uptake.

Approval Year

PubMed

PubMed

TitleDatePubMed
Potential anti-diabetic applications of a new molecule with affinity for beta 3-adrenoceptors.
1996
Effects on energy utilization of a beta3-adrenergic agonist in rats fed on a cafeteria diet.
1997 Sep
Effects of trecadrine, a beta 3-adrenergic agonist, on intestinal absorption of D-galactose and disaccharidase activities in three physiopathological models.
1997 Sep
Effect of different beta-adrenergic agonists on the intestinal absorption of galactose and phenylalanine.
1998 Aug
Leptin, but not a beta 3-adrenergic agonist, upregulates muscle uncoupling protein-3 messenger RNA expression: short-term thermogenic interactions.
1999 Jun
A beta3-adrenergic agonist increases muscle GLUT1/GLUT4 ratio, and regulates liver glucose utilization in diabetic rats.
1999 Mar
Effect of a beta3-adrenergic agonist on liver glucokinase gene expression in alloxan-diabetic rats.
1999 Mar
Hypolipidemic properties of a diphenyl-methylen-ethylamine derivative with affinity for beta 3-adrenoceptors in a model of hypercholesterolemia.
1999 Oct 30
Up-regulation of muscle UCP2 gene expression by a new beta3-adrenoceptor agonist, trecadrine, in obese (cafeteria) rodents, but down-regulation in lean animals.
2000 Feb
Effects of the oral administration of a beta3-adrenergic agonist on lipid metabolism in alloxan-diabetic rats.
2000 Jul
Free fatty acids are involved in the inverse relationship between hormone-sensitive lipase (HSL) activity and expression in adipose tissue after high-fat feeding or beta3-adrenergic stimulation.
2000 May
Divergent effects of an alpha2-adrenergic antagonist on lipolysis and thermogenesis: interactions with a beta3-adrenergic agonist in rats.
2001 Jul
Rapid in vivo PGC-1 mRNA upregulation in brown adipose tissue of Wistar rats by a beta(3)-adrenergic agonist and lack of effect of leptin.
2001 May 15
Effects of Trecadrine, a beta3-adrenergic agonist, on leptin secretion, glucose and lipid metabolism in isolated rat adipocytes.
2002 Jul
Interactions between an alpha2-adrenergic antagonist and a beta3-adrenergic agonist on the expression of UCP2 and UCP3 in rats.
2002 Mar
Effects of a beta3-adrenergic agonist on glucose uptake and leptin expression and secretion in cultured adipocytes from lean and overweight (cafeteria) rats.
2002 Mar 15
Effects of a beta3-adrenergic agonist on the immune response in diet-induced (cafeteria) obese animals.
2003 Sep
Patents

Patents

Name Type Language
TRECADRINE
INN  
INN  
Official Name English
trecadrine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
Code System Code Type Description
MESH
C101319
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
FDA UNII
34H206R8A5
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
CAS
90845-56-0
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
PUBCHEM
11740693
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL2304037
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
SMS_ID
100000077498
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
EVMPD
SUB11227MIG
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
INN
5651
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY
NCI_THESAURUS
C66619
Created by admin on Sat Dec 16 17:37:57 GMT 2023 , Edited by admin on Sat Dec 16 17:37:57 GMT 2023
PRIMARY