Fexaramine | CAS#574013-66-4 | agonist of the farnesoid X receptor

MedKoo Cat#: 317116 | Name: Fexaramine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fexaramine is an agonist of the farnesoid X receptor (FXR), which is a bile acid-activated nuclear receptor that controls bile-acid synthesis, conjugation and transport, as well as lipid metabolism through actions in the liver and intestine. Fexaramine has 100-fold greater affinity for FXR than natural compounds and described the genomic targets and binding site on FXR. When administered orally to mice, fexaramine produced selective actions through FXR receptors in the intestines.

Chemical Structure

Fexaramine

CAS#574013-66-4

Theoretical Analysis

MedKoo Cat#: 317116

Name: Fexaramine

CAS#: 574013-66-4

Chemical Formula: C32H36N2O3

Exact Mass: 496.2726

Molecular Weight: 498.65

Elemental Analysis: C, 77.39; H, 7.31; N, 5.64; O, 9.66

Price and Availability

Size	Price	Availability
100mg	USD 750.00	2 Weeks
200mg	USD 1,150.00	2 Weeks
500mg	USD 1,850.00	2 Weeks
1g	USD 2,950.00	2 Weeks

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Related CAS #

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Synonym

Fexaramine

IUPAC/Chemical Name

methyl (E)-3-(3-(N-((4'-(dimethylamino)-[1,1'-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate

InChi Key

VLQTUNDJHLEFEQ-KGENOOAVSA-N

InChi Code

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+

SMILES Code

O=C(OC)/C=C/C1=CC=CC(N(C(C2CCCCC2)=O)CC3=CC=C(C4=CC=C(N(C)C)C=C4)C=C3)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Fexaramine is a potent and selective FXR agonist with an EC50 of 25 nM.

In vitro activity:

BMMs differentiated into mature TRAP-positive (TRAP+) multinucleated osteoclasts (MNCs) during the culture period, while treatment with fexaramine inhibited osteoclast differentiation in a dose-dependent manner (Fig. 1A). Reference: J Bone Metab. 2017 Nov; 24(4): 207–215. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5734945/

In vivo activity:

This study finally evaluated the in vivo effect of fexaramine on osteoclast formation, using a LPS-challenged mouse model. In parallel with the effects in vitro, fexaramine notably reduced LPS-induced osteoclast formation (Fig. 5B). Collectively, this study conclude that fexaramine has an inhibitory effect on inflammation-induced osteoclastogenesis in vivo. Reference: J Bone Metab. 2017 Nov; 24(4): 207–215. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5734945/

	Solvent	mg/mL	mM
Solubility
	DMSO	36.6	73.30
	DMF	30.0	60.16

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 498.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zheng T, Kim NY, Yim M. Fexaramine Inhibits Receptor Activator of Nuclear Factor-κB Ligand-induced Osteoclast Formation via Nuclear Factor of Activated T Cells Signaling Pathways. J Bone Metab. 2017 Nov;24(4):207-215. doi: 10.11005/jbm.2017.24.4.207. Epub 2017 Nov 30. PMID: 29259959; PMCID: PMC5734945.

In vitro protocol:

In vivo protocol:

1: Kim Y, Chang KO. Fexaramine as an entry blocker for feline caliciviruses. Antiviral Res. 2018 Apr;152:76-83. doi: 10.1016/j.antiviral.2018.02.009. Epub 2018 Feb 15. PMID: 29454892; PMCID: PMC7125566. 2: Fu T, Li Y, Oh TG, Cayabyab F, He N, Tang Q, Coulter S, Truitt M, Medina P, He M, Yu RT, Atkins A, Zheng Y, Liddle C, Downes M, Evans RM. FXR mediates ILC- intrinsic responses to intestinal inflammation. Proc Natl Acad Sci U S A. 2022 Dec 20;119(51):e2213041119. doi: 10.1073/pnas.2213041119. Epub 2022 Dec 12. PMID: 36508655; PMCID: PMC9907109. 3: Fang S, Suh JM, Reilly SM, Yu E, Osborn O, Lackey D, Yoshihara E, Perino A, Jacinto S, Lukasheva Y, Atkins AR, Khvat A, Schnabl B, Yu RT, Brenner DA, Coulter S, Liddle C, Schoonjans K, Olefsky JM, Saltiel AR, Downes M, Evans RM. Intestinal FXR agonism promotes adipose tissue browning and reduces obesity and insulin resistance. Nat Med. 2015 Feb;21(2):159-65. doi: 10.1038/nm.3760. Epub 2015 Jan 5. PMID: 25559344; PMCID: PMC4320010. 4: Zheng T, Kim NY, Yim M. Fexaramine Inhibits Receptor Activator of Nuclear Factor-κB Ligand-induced Osteoclast Formation via Nuclear Factor of Activated T Cells Signaling Pathways. J Bone Metab. 2017 Nov;24(4):207-215. doi: 10.11005/jbm.2017.24.4.207. Epub 2017 Nov 30. PMID: 29259959; PMCID: PMC5734945. 5: Hartmann P, Hochrath K, Horvath A, Chen P, Seebauer CT, Llorente C, Wang L, Alnouti Y, Fouts DE, Stärkel P, Loomba R, Coulter S, Liddle C, Yu RT, Ling L, Rossi SJ, DePaoli AM, Downes M, Evans RM, Brenner DA, Schnabl B. Modulation of the intestinal bile acid/farnesoid X receptor/fibroblast growth factor 15 axis improves alcoholic liver disease in mice. Hepatology. 2018 Jun;67(6):2150-2166. doi: 10.1002/hep.29676. Epub 2018 Apr 16. PMID: 29159825; PMCID: PMC5962369. 6: Sorribas M, Jakob MO, Yilmaz B, Li H, Stutz D, Noser Y, de Gottardi A, Moghadamrad S, Hassan M, Albillos A, Francés R, Juanola O, Spadoni I, Rescigno M, Wiest R. FXR modulates the gut-vascular barrier by regulating the entry sites for bacterial translocation in experimental cirrhosis. J Hepatol. 2019 Dec;71(6):1126-1140. doi: 10.1016/j.jhep.2019.06.017. Epub 2019 Jul 8. PMID: 31295531. 7: Pathak P, Xie C, Nichols RG, Ferrell JM, Boehme S, Krausz KW, Patterson AD, Gonzalez FJ, Chiang JYL. Intestine farnesoid X receptor agonist and the gut microbiota activate G-protein bile acid receptor-1 signaling to improve metabolism. Hepatology. 2018 Oct;68(4):1574-1588. doi: 10.1002/hep.29857. Epub 2018 May 21. PMID: 29486523; PMCID: PMC6111007. 8: Wang H, Zhao Z, Zhou J, Guo Y, Wang G, Hao H, Xu X. A novel intestinal- restricted FXR agonist. Bioorg Med Chem Lett. 2017 Aug 1;27(15):3386-3390. doi: 10.1016/j.bmcl.2017.06.003. Epub 2017 Jun 3. Erratum in: Bioorg Med Chem Lett. 2017 Dec 1;27(23 ):5353. PMID: 28629595. 9: Shim S, Krishnaiah M, Sankham MR, Kim I, Lee Y, Shin I, Oh AR, Lee HJ, Vu TNL, Park J, Choi S, Park S, Kwon Y, Fang S, Kim DK. Discovery of (E)-3-( 3-((2-Cyano-4'-dimethylaminobiphenyl-4-ylmethyl)cyclohexanecarbonylamino)-5-fluo rophenyl)acrylic Acid Methyl Ester, an Intestine-Specific, FXR Partial Agonist for the Treatment of Nonalcoholic Steatohepatitis. J Med Chem. 2022 Jul 28;65(14):9974-10000. doi: 10.1021/acs.jmedchem.2c00641. Epub 2022 Jul 7. PMID: 35797110. 10: Qiu Y, Yu J, Ji X, Yu H, Xue M, Zhang F, Li Y, Bao Z. Ileal FXR-FGF15/19 signaling activation improves skeletal muscle loss in aged mice. Mech Ageing Dev. 2022 Mar;202:111630. doi: 10.1016/j.mad.2022.111630. Epub 2022 Jan 10. PMID: 35026209. 11: Downes M, Verdecia MA, Roecker AJ, Hughes R, Hogenesch JB, Kast-Woelbern HR, Bowman ME, Ferrer JL, Anisfeld AM, Edwards PA, Rosenfeld JM, Alvarez JG, Noel JP, Nicolaou KC, Evans RM. A chemical, genetic, and structural analysis of the nuclear bile acid receptor FXR. Mol Cell. 2003 Apr;11(4):1079-92. doi: 10.1016/s1097-2765(03)00104-7. PMID: 12718892; PMCID: PMC6179153. 12: Xu M, Shen Y, Cen M, Zhu Y, Cheng F, Tang L, Zheng X, Kim JJ, Dai N, Hu W. Modulation of the Gut Microbiota-farnesoid X Receptor Axis Improves Deoxycholic Acid-induced Intestinal Inflammation in Mice. J Crohns Colitis. 2021 Jul 5;15(7):1197-1210. doi: 10.1093/ecco-jcc/jjab003. PMID: 33417675. 13: Yin Y, Wang M, Gu W, Chen L. Intestine-specific FXR agonists as potential therapeutic agents for colorectal cancer. Biochem Pharmacol. 2021 Apr;186:114430. doi: 10.1016/j.bcp.2021.114430. Epub 2021 Feb 6. PMID: 33556338. 14: Lam TK. Hepatic glucose metabolism in 2015: Nutrient and hormone-sensing- dependent regulation. Nat Rev Endocrinol. 2016 Feb;12(2):70-2. doi: 10.1038/nrendo.2015.204. Epub 2015 Nov 27. PMID: 26610410. 15: De Magalhaes Filho CD, Downes M, Evans RM. Farnesoid X Receptor an Emerging Target to Combat Obesity. Dig Dis. 2017;35(3):185-190. doi: 10.1159/000450909. Epub 2017 Mar 1. PMID: 28249279; PMCID: PMC5417073. 16: Liu Y, Kang W, Liu S, Li J, Liu J, Chen X, Gan F, Huang K. Gut microbiota- bile acid-intestinal Farnesoid X receptor signaling axis orchestrates cadmium- induced liver injury. Sci Total Environ. 2022 Nov 25;849:157861. doi: 10.1016/j.scitotenv.2022.157861. Epub 2022 Aug 5. PMID: 35934034. 17: Claudel T, Sturm E, Kuipers F, Staels B. The farnesoid X receptor: a novel drug target? Expert Opin Investig Drugs. 2004 Sep;13(9):1135-48. doi: 10.1517/13543784.13.9.1135. PMID: 15330745. 18: Cao L, Qin R, Liu J. Farnesoid X receptor protects against lipopolysaccharide-induced endometritis by inhibiting ferroptosis and inflammatory response. Int Immunopharmacol. 2023 May;118:110080. doi: 10.1016/j.intimp.2023.110080. Epub 2023 Mar 29. PMID: 37001382. 19: Gillard J, Picalausa C, Ullmer C, Adorini L, Staels B, Tailleux A, Leclercq IA. Enterohepatic Takeda G-Protein Coupled Receptor 5 Agonism in Metabolic Dysfunction-Associated Fatty Liver Disease and Related Glucose Dysmetabolism. Nutrients. 2022 Jun 29;14(13):2707. doi: 10.3390/nu14132707. PMID: 35807885; PMCID: PMC9268629. 20: Cho SW, An JH, Park H, Yang JY, Choi HJ, Kim SW, Park YJ, Kim SY, Yim M, Baek WY, Kim JE, Shin CS. Positive regulation of osteogenesis by bile acid through FXR. J Bone Miner Res. 2013 Oct;28(10):2109-21. doi: 10.1002/jbmr.1961. PMID: 23609136.