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SML1390

Sigma-Aldrich

Fexaramine

≥98% (HPLC)

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Synonym(s):
3-[3-[(Cyclohexylcarbonyl)[[4′-(dimethylamino)[1,1′-biphenyl]-4-yl]methyl]amino]phenyl]-2-propenoic acid methyl ester
Empirical Formula (Hill Notation):
C32H36N2O3
CAS Number:
Molecular Weight:
496.64
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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SML0881SML1680SML1327
Fexaramine ≥98% (HPLC)

Sigma-Aldrich

SML1390

Fexaramine

Ex26 ≥98% (HPLC)

Sigma-Aldrich

SML1680

Ex26

form

powder

form

powder

form

powder

form

powder

storage condition

desiccated

storage condition

desiccated

storage condition

-

storage condition

-

color

white to beige

color

white to beige

color

white to beige

color

white to beige

solubility

DMSO: 10 mg/mL, clear

solubility

H2O: 15 mg/mL, clear

solubility

DMSO: 25 mg/mL, clear

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

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 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 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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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)
Farnesoid X receptor modulators (2011?2014): a patent review.
Sepe V, et al.
Expert Opinion on Therapeutic Patents, 25(8), 885-896 (2015)

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