Agonist of farnesoid X receptor (FXR)
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6-ECDCA

Item No. 11031

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β,6α,7α)-6-ethyl-3,7-dihydroxy-cholan-24-oic acid
CAS Number
459789-99-2
Synonyms
  • ​6α-ethyl Chenodeoxycholic Acid
  • INT 747
  • Obeticholic Acid
Molecular Formula
C26H44O4
Formula Weight
420.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O[C@@H]1CC[C@@]2(C)[C@@]([C@@H](CC)[C@@H](O)[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCC(O)=O)C)([H])C1
InChi Code
InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1
InChi Key
ZXERDUOLZKYMJM-ZWECCWDJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Farnesoid X receptor (FXR) is a nuclear receptor that is activated by bile acid, with chenodeoxycholic acid (CDCA) being a representative natural ligand.1 6-ECDCA is a synthetic bile acid that acts as a potent and selective agonist of FXR (EC50 = 99 nM).2 Through FXR, it alters gene expression that results in protection against cholestasis as well as liver fibrosis in animal models.2,3,4 6-ECDCA also, through FXR, promotes the differentiation of adipocytes and enhances insulin signaling in mature adipocytes.5 In ApoE-/- mice, 6-ECDCA ameliorates vascular calcification secondary to chronic kidney disease without affecting the development of atherosclerosis.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rizzo, G., Renga, B., Antonelli, E., et al. The methyl transferase PRMT1 functions as co-activator of farnesoid X receptor (FXR)/9-cis retinoid X receptor and regulates transcription of FXR responsive genes. Mol. Pharmacol. 68(2), 551-558 (2005).

    2. Pellicciari, R., Fiorucci, S., Camaioni, E., et al. 6α-ethyl-chenodeoxycholic acid (6-ECDCA), a potent and selective FXR agonist endowed with anticholestatic activity. J. Med. Chem. 45(17), 3569-3572 (2002).

    3. Fiorucci, S., Clerici, C., Antonelli, E., et al. Protective effects of 6-ethyl chenodeoxycholic acid, a farnesoid X receptor ligand, in estrogen-induced cholestasis. J. Pharmacol. Exp. Ther. 313(2), 604-612 (2005).

    4. Fiorucci, S., Rizzo, G., Antonelli, E., et al. A farnesoid X receptor-small heterodimer partner regulatory cascade modulates tissue metalloproteinase inhibitor-1 and matrix metalloprotease expression in hepatic stellate cells and promotes resolution of liver fibrosis. J. Pharmacol. Exp. Ther. 314(2), 584-595 (2005).

    5. Rizzo, G., Disante, M., Mencarelli, A., et al. The farnesoid X receptor promotes adipocyte differentiation and regulates adipose cell function in vivo. Mol. Pharmacol. 70(4), 1164-1173 (2006).

    6. Miyazaki-Anzai, S., Levi, M., Kratzer, A., et al. Farnesoid X receptor activation prevents the development of vascular calcification in ApoE-/- mice with chronic kidney disease. Circ. Res. 106(12), 1807-1817 (2010).