Fexaramine
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MedKoo CAT#: 317116

CAS#: 574013-66-4

Description: 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

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Fexaramine
CAS# 574013-66-4

Theoretical Analysis

MedKoo Cat#: 317116
Name: Fexaramine
CAS#: 574013-66-4
Chemical Formula: C32H36N2O3
Exact Mass: 496.27259
Molecular Weight: 498.65
Elemental Analysis: C, 77.39; H, 7.31; N, 5.64; O, 9.66

Price and Availability

Size Price Availability Quantity
100.0mg USD 750.0 2 Weeks
200.0mg USD 1150.0 2 Weeks
500.0mg USD 1850.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 4250.0 2 Weeks
5.0g USD 7650.0 2 Weeks
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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

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.

Recalculate based on batch purity %
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

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1: Cully M. Obesity and diabetes: FXR and JAK step up to BAT. Nat Rev Drug Discov. 2015 Feb;14(2):91. doi: 10.1038/nrd4543. PubMed PMID: 25633788.

2: 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. PubMed PMID: 25559344; PubMed Central PMCID: PMC4320010.

3: 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. PubMed PMID: 23609136.

4: van der Poorten D, Samer CF, Ramezani-Moghadam M, Coulter S, Kacevska M, Schrijnders D, Wu LE, McLeod D, Bugianesi E, Komuta M, Roskams T, Liddle C, Hebbard L, George J. Hepatic fat loss in advanced nonalcoholic steatohepatitis: are alterations in serum adiponectin the cause? Hepatology. 2013 Jun;57(6):2180-8. doi: 10.1002/hep.26072. Epub 2013 Jan 18. PubMed PMID: 22996622.

5: Li WH, Fu J, Zheng MY, Liu GX, Tang Y. [Progress in the ligands and their complex structures of farnesoid X receptor]. Yao Xue Xue Bao. 2012 Jun;47(6):704-15. Review. Chinese. PubMed PMID: 22919716.

6: Lam IP, Lee LT, Choi HS, Alpini G, Chow BK. Bile acids inhibit duodenal secretin expression via orphan nuclear receptor small heterodimer partner (SHP). Am J Physiol Gastrointest Liver Physiol. 2009 Jul;297(1):G90-7. doi: 10.1152/ajpgi.00094.2009. Epub 2009 Apr 16. PubMed PMID: 19372104; PubMed Central PMCID: PMC2711755.

7: Soisson SM, Parthasarathy G, Adams AD, Sahoo S, Sitlani A, Sparrow C, Cui J, Becker JW. Identification of a potent synthetic FXR agonist with an unexpected mode of binding and activation. Proc Natl Acad Sci U S A. 2008 Apr 8;105(14):5337-42. doi: 10.1073/pnas.0710981105. Epub 2008 Apr 7. PubMed PMID: 18391212; PubMed Central PMCID: PMC2291122.

8: Cai SY, Xiong L, Wray CG, Ballatori N, Boyer JL. The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1400-9. Epub 2007 Jun 13. PubMed PMID: 17567710.

9: Zhang T, Zhou JH, Shi LW, Zhu RX, Chen MB. 3D-QSAR studies with the aid of molecular docking for a series of non-steroidal FXR agonists. Bioorg Med Chem Lett. 2007 Apr 15;17(8):2156-60. Epub 2007 Jan 31. PubMed PMID: 17307356.

10: 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. Review. PubMed PMID: 15330745.

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. PubMed PMID: 12718892.

Fexaramine

100.0mg / USD 750.0