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SML1390

Fexaramine

≥98% (HPLC)

Synonym(s):

3-[3-[(Cyclohexylcarbonyl)[[4′-(dimethylamino)[1,1′-biphenyl]-4-yl]methyl]amino]phenyl]-2-propenoic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C32H36N2O3
CAS Number:
574013-66-4
Molecular Weight:
496.64
NACRES:
NA.77
PubChem Substance ID:
329825838
UNSPSC Code:
12352116
MDL number:
MFCD09971007
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated
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Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN(C)C(C=C1)=CC=C1C2=CC=C(CN(C3=CC=CC(/C=C/C(OC)=O)=C3)C(C4CCCCC4)=O)C=C2

InChI

1S/C32H36N2O3/c1-33(2)29-19-17-27(18-20-29)26-15-12-25(13-16-26)23-34(32(36)28-9-5-4-6-10-28)30-11-7-8-24(22-30)14-21-31(35)37-3/h7-8,11-22,28H,4-6,9-10,23H2,1-3H3/b21-14+

InChI key

VLQTUNDJHLEFEQ-KGENOOAVSA-N

General description

Fexaramine belongs to the nuclear hormone receptor family.

Application

Fexaramine has been used to study its action on RANKL (receptor activator of nuclear factor-κB ligand)-induced osteoclastogenesis in mouse model.

Biochem/physiol Actions

Fexaramine might regulate lipid and glucose metabolism and can serve as a therapeutic target in the treatment of fatty liver disease, type 2 diabetes and obesity. Fexaramine might mediate cholesterol homeostasis and promotes osteoblast differentiation and suppresses differentiation of osteoclast.
Fexaramine is a potent and selective agonist of the bile acid sensor farnesoid X receptor (FXR) in the gut with an EC50 of 25 nM and no activity found for other nuclear receptors. Fexaramine induces enteric fibroblast growth factor 15 (FGF15), causing alterations in bile acid composition without activating FXR target genes in the liver. In mouse studies, fexaramine enhanced thermogenesis and browning of white adipose tissue while reducing diet-induced weight gain, body-wide inflammation and hepatic glucose production. Fexaramine also improved insulin responsiveness.
Fexaramine is an agonist of the farnesoid X receptor (FXR).

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H413

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000367760
0000367760
0000066368
0000066371
0000029620

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Farnesoid X receptor modulators (2011?2014): a patent review.
Sepe V, et al.
Expert Opinion on Therapeutic Patents, 25(8), 885-896 (2015)
Fexaramine Inhibits Receptor Activator of Nuclear Factor-?B Ligand-induced Osteoclast Formation via Nuclear Factor of Activated T Cells Signaling Pathways.
Zheng T, et al.
Journal of bone metabolism, 24(4), 207-215 (2017)

Global Trade Item Number

SKUGTIN
SML1390-25MG04061833225929
SML1390-5MG04061833225936

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