Home Other Building Blocks 459789-99-2
459789-99-2,MFCD16621104
Catalog No.:AA00365Z

459789-99-2 | Obetichloic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
25mg
95%
in stock  
$40.00   $28.00
- +
1g
98%
in stock  
$48.00   $34.00
- +
5g
98%
in stock  
$149.00   $104.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00365Z
Chemical Name:
Obetichloic acid
CAS Number:
459789-99-2
Molecular Formula:
C26H44O4
Molecular Weight:
420.6252
MDL Number:
MFCD16621104
SMILES:
CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@H]1C[C@H](O)CC2)C)[C@@H](CCC(=O)O)C
Properties
Properties
 
BP:
562.9°C at 760 mmHg  
Form:
Solid  
MP:
>98ºC (dec.)  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
649  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
5  
XLogP3:
5.7  

Downstream Synthesis Route
633-65-8   
obeticholicacid 
 
C26H43O4(1-)*C20H18NO4(1+) 

[1]CurrentPatentAssignee:HEFEIHUAFANGPHARMACEUTICALSCIENCESTECHNOLOGY-CN105693805,2016,ALocationinpatent:Paragraph0040;0041;0042

[1]CurrentPatentAssignee:SHAANXISYNTHETICPHARMACEUTICAL-CN106478759,2017,ALocationinpatent:Paragraph0030;0031

Literature

Title: Yangonin protects against cholestasis and hepatotoxity via activation of farnesoid X receptor in vivo and in vitro.

Journal: Toxicology and applied pharmacology 20180601

Title: Steviol, an aglycone of steviol glycoside sweeteners, interacts with the pregnane X (PXR) and aryl hydrocarbon (AHR) receptors in detoxification regulation.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20171101

Title: Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20170301

Title: Dihydroartemisinin protects against alcoholic liver injury through alleviating hepatocyte steatosis in a farnesoid X receptor-dependent manner.

Journal: Toxicology and applied pharmacology 20170115

Title: Acetylated deoxycholic (DCA) and cholic (CA) acids are potent ligands of pregnane X (PXR) receptor.

Journal: Toxicology letters 20170104

Title: Obeticholic acid protects against carbon tetrachloride-induced acute liver injury and inflammation.

Journal: Toxicology and applied pharmacology 20170101

Title: Pyrazinamide Induced Rat Cholestatic Liver Injury through Inhibition of FXR Regulatory Effect on Bile Acid Synthesis and Transport.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20160801

Title: Obeticholic Acid: First Global Approval.

Journal: Drugs 20160801

Title: Farnesoid X Receptor Protects against Kidney Injury in Uninephrectomized Obese Mice.

Journal: The Journal of biological chemistry 20160129

Title: Synthetic farnesoid X receptor agonists induce high-density lipoprotein-mediated transhepatic cholesterol efflux in mice and monkeys and prevent atherosclerosis in cholesteryl ester transfer protein transgenic low-density lipoprotein receptor (-/-) mice.

Journal: The Journal of pharmacology and experimental therapeutics 20121201

Title: An improved synthesis of 6α-ethylchenodeoxycholic acid (6ECDCA), a potent and selective agonist for the Farnesoid X Receptor (FXR).

Journal: Steroids 20121101

Title: Testosterone and farnesoid X receptor agonist INT-747 counteract high fat diet-induced bladder alterations in a rabbit model of metabolic syndrome.

Journal: The Journal of steroid biochemistry and molecular biology 20121001

Title: Glucocorticoid receptor mediates the gluconeogenic activity of the farnesoid X receptor in the fasting condition.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20120701

Title: Conicasterol E, a small heterodimer partner sparing farnesoid X receptor modulator endowed with a pregnane X receptor agonistic activity, from the marine sponge Theonella swinhoei.

Journal: Journal of medicinal chemistry 20120112

Title: Testosterone protects from metabolic syndrome-associated prostate inflammation: an experimental study in rabbit.

Journal: The Journal of endocrinology 20120101

Title: FXR protects lung from lipopolysaccharide-induced acute injury.

Journal: Molecular endocrinology (Baltimore, Md.) 20120101

Title: Farnesoid X receptor agonist for the treatment of liver and metabolic disorders: focus on 6-ethyl-CDCA.

Journal: Mini reviews in medicinal chemistry 20110801

Title: Farnesoid X receptor agonists for primary biliary cirrhosis.

Journal: Current opinion in gastroenterology 20110501

Title: Farnesoid X receptor activation inhibits inflammation and preserves the intestinal barrier in inflammatory bowel disease.

Journal: Gut 20110401

Title: Synthesis and pharmacological validation of a novel series of non-steroidal FXR agonists.

Journal: Bioorganic & medicinal chemistry letters 20100815

Title: Farnesoid X receptor activation prevents the development of vascular calcification in ApoE-/- mice with chronic kidney disease.

Journal: Circulation research 20100625

Title: Pharmacotherapy of cholestatic liver diseases.

Journal: Journal of digestive diseases 20100601

Title: FXR activation reverses insulin resistance and lipid abnormalities and protects against liver steatosis in Zucker (fa/fa) obese rats.

Journal: Journal of lipid research 20100401

Title: Discovery of 6alpha-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a potent and selective agonist for the TGR5 receptor, a novel target for diabesity.

Journal: Journal of medicinal chemistry 20091224

Title: The farnesoid X receptor modulates renal lipid metabolism and diet-induced renal inflammation, fibrosis, and proteinuria.

Journal: American journal of physiology. Renal physiology 20091201

Title: Farnesoid x receptor ligands inhibit vascular smooth muscle cell inflammation and migration.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20071201

Title: Nongenomic actions of bile acids. Synthesis and preliminary characterization of 23- and 6,23-alkyl-substituted bile acid derivatives as selective modulators for the G-protein coupled receptor TGR5.

Journal: Journal of medicinal chemistry 20070906

Title: The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20070901

Title: The farnesoid X receptor promotes adipocyte differentiation and regulates adipose cell function in vivo.

Journal: Molecular pharmacology 20061001

Title: Back door modulation of the farnesoid X receptor: design, synthesis, and biological evaluation of a series of side chain modified chenodeoxycholic acid derivatives.

Journal: Journal of medicinal chemistry 20060713

Title: Nuclear receptors, bile-acid detoxification, and cholestasis.

Journal: Lancet (London, England) 20060211

Title: Cross-talk between farnesoid-X-receptor (FXR) and peroxisome proliferator-activated receptor gamma contributes to the antifibrotic activity of FXR ligands in rodent models of liver cirrhosis.

Journal: The Journal of pharmacology and experimental therapeutics 20051001

Title: 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.

Journal: The Journal of pharmacology and experimental therapeutics 20050801

Title: 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.

Journal: Molecular pharmacology 20050801

Title: Protective effects of 6-ethyl chenodeoxycholic acid, a farnesoid X receptor ligand, in estrogen-induced cholestasis.

Journal: The Journal of pharmacology and experimental therapeutics 20050501

Title: The nuclear receptor SHP mediates inhibition of hepatic stellate cells by FXR and protects against liver fibrosis.

Journal: Gastroenterology 20041101

Title: The farnesoid X receptor: a novel drug target?

Journal: Expert opinion on investigational drugs 20040901

Title: Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid.

Journal: Journal of medicinal chemistry 20040826

Title: Binding mode of 6ECDCA, a potent bile acid agonist of the farnesoid X receptor (FXR).

Journal: Bioorganic & medicinal chemistry letters 20030602

Title: 6alpha-ethyl-chenodeoxycholic acid (6-ECDCA), a potent and selective FXR agonist endowed with anticholestatic activity.

Journal: Journal of medicinal chemistry 20020815

Title: Nuclear receptors and lipid physiology: opening the X-files.

Journal: Science (New York, N.Y.) 20011130

Title: Identification of a nuclear receptor for bile acids.

Journal: Science (New York, N.Y.) 19990521

Title: Pellicciari R, et al. 6alpha-ethyl-chenodeoxycholic acid (6-ECDCA), a potent and selective FXR agonist endowed with anticholestatic activity. J Med Chem. 2002 Aug 15;45(17):3569-72.

Title: Fiorucci S, et al. Protective effects of 6-ethyl chenodeoxycholic acid, a farnesoid X receptor ligand, in estrogen-induced cholestasis. J Pharmacol Exp Ther. 2005 May;313(2):604-12.

Title: Ghebremariam YT, et al. FXR agonist INT-747 upregulates DDAH expression and enhances sensitivity in high-salt fed Dahl rats. PLoS One. 2013 Apr 4;8(4):e60653.

Title: Verbeke L, et al. The FXR Agonist Obeticholic Acid Prevents Gut Barrier Dysfunction and Bacterial Translocation in Cholestatic Rats. Am J Pathol. 2015 Feb;185(2):409-19.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:459789-99-2 Molecular Formula|459789-99-2 MDL|459789-99-2 SMILES|459789-99-2 Obetichloic acid