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=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
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 |
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Effects on energy utilization of a beta3-adrenergic agonist in rats fed on a cafeteria diet. | 1997 Sep |
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Effects of trecadrine, a beta 3-adrenergic agonist, on intestinal absorption of D-galactose and disaccharidase activities in three physiopathological models. | 1997 Sep |
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Effect of different beta-adrenergic agonists on the intestinal absorption of galactose and phenylalanine. | 1998 Aug |
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Effect of a beta3-adrenergic agonist on liver glucokinase gene expression in alloxan-diabetic rats. | 1999 Mar |
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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 |
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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 |
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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 |
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Effects of Trecadrine, a beta3-adrenergic agonist, on leptin secretion, glucose and lipid metabolism in isolated rat adipocytes. | 2002 Jul |
Patents
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C48149
Created by
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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
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ACTIVE MOIETY