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
SMILES
C[C@@H]([C@H](O)C1=CC=CC=C1)N(C)CC=C2C3=CC=CC=C3CCC4=CC=CC=C24
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
| Molecular Formula | C27H29NO |
| Molecular Weight | 383.5253 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of a beta3-adrenergic agonist on the immune response in diet-induced (cafeteria) obese animals. | 2003-09 |
|
| Effects of Trecadrine, a beta3-adrenergic agonist, on leptin secretion, glucose and lipid metabolism in isolated rat adipocytes. | 2002-07 |
|
| Effects of a beta3-adrenergic agonist on glucose uptake and leptin expression and secretion in cultured adipocytes from lean and overweight (cafeteria) rats. | 2002-03-15 |
|
| Interactions between an alpha2-adrenergic antagonist and a beta3-adrenergic agonist on the expression of UCP2 and UCP3 in rats. | 2002-03 |
|
| Divergent effects of an alpha2-adrenergic antagonist on lipolysis and thermogenesis: interactions with a beta3-adrenergic agonist in rats. | 2001-07 |
|
| 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. | 2001-05-15 |
|
| Effects of the oral administration of a beta3-adrenergic agonist on lipid metabolism in alloxan-diabetic rats. | 2000-07 |
|
| 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. | 2000-05 |
|
| Up-regulation of muscle UCP2 gene expression by a new beta3-adrenoceptor agonist, trecadrine, in obese (cafeteria) rodents, but down-regulation in lean animals. | 2000-02 |
|
| Hypolipidemic properties of a diphenyl-methylen-ethylamine derivative with affinity for beta 3-adrenoceptors in a model of hypercholesterolemia. | 1999-10-30 |
|
| Leptin, but not a beta 3-adrenergic agonist, upregulates muscle uncoupling protein-3 messenger RNA expression: short-term thermogenic interactions. | 1999-06 |
|
| A beta3-adrenergic agonist increases muscle GLUT1/GLUT4 ratio, and regulates liver glucose utilization in diabetic rats. | 1999-03 |
|
| Effect of a beta3-adrenergic agonist on liver glucokinase gene expression in alloxan-diabetic rats. | 1999-03 |
|
| Effect of different beta-adrenergic agonists on the intestinal absorption of galactose and phenylalanine. | 1998-08 |
|
| Effects on energy utilization of a beta3-adrenergic agonist in rats fed on a cafeteria diet. | 1997-09 |
|
| Effects of trecadrine, a beta 3-adrenergic agonist, on intestinal absorption of D-galactose and disaccharidase activities in three physiopathological models. | 1997-09 |
|
| Potential anti-diabetic applications of a new molecule with affinity for beta 3-adrenoceptors. | 1996 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:23:55 GMT 2025
by
admin
on
Wed Apr 02 09:23:55 GMT 2025
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| Record UNII |
34H206R8A5
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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Preferred Name | English | ||
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Official Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C48149
Created by
admin on Wed Apr 02 09:23:55 GMT 2025 , Edited by admin on Wed Apr 02 09:23:55 GMT 2025
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| Code System | Code | Type | Description | ||
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C101319
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34H206R8A5
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90845-56-0
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11740693
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CHEMBL2304037
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100000077498
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SUB11227MIG
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5651
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C66619
Created by
admin on Wed Apr 02 09:23:55 GMT 2025 , Edited by admin on Wed Apr 02 09:23:55 GMT 2025
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |