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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H23ClN2O4
Molecular Weight 402.871
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAFABEGRON

SMILES

C[C@H](CC1=CNC2=C1C=CC=C2OCC(O)=O)NC[C@H](O)C3=CC(Cl)=CC=C3

InChI

InChIKey=FHEYFIGWYQJVDR-ACJLOTCBSA-N
InChI=1S/C21H23ClN2O4/c1-13(23-11-18(25)14-4-2-5-16(22)9-14)8-15-10-24-21-17(15)6-3-7-19(21)28-12-20(26)27/h2-7,9-10,13,18,23-25H,8,11-12H2,1H3,(H,26,27)/t13-,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H23ClN2O4
Molecular Weight 402.871
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Rafabegron (also known as TAK-677 ) is an indole derivative patented by Dainippon Pharmaceutical Co., Ltd., as antidiabetics and antiobesity agent. Rafabegron asts as beta3-adrenergic agonist. In preclinical studies Rafabegron reduced the total weight of white adipose tissues by reducing the size of the adipocytes, an effect associated with the normalization of tumor necrosis factor-alpha and leptin expression levels in micce. The levels of uncoupling protein (UCP)-1 mRNA in brown adipose tissue were increased threefold. Rafabegron caused a marked increase (20- to 80-fold) in the expression of UCP-1 in white adipose tissues. In clinical trials. Rafabegron has no effect on 24-h respiratory quotient or fat oxidation but does slightly increase 24-h energy expenditure at the highest dose. The acute studies showed large interindividual variability in plasma concentrations of Rafabegron indicating some possible problems with bioavailability and therefore efficacy. Based on these data further development was discontinued.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
0.1 mg or 0.5 mg twice daily
Route of Administration: Oral
Substance Class Chemical
Record UNII
LN3E1Q0SU2
Record Status Validated (UNII)
Record Version