99697-24-2

Usage

Uses

Used in Pharmaceutical Industry:
24-norursodeoxycholic acid is used as a therapeutic agent for the treatment of sclerosing cholangitis, a chronic liver disease characterized by inflammation and fibrosis of the bile ducts. It is particularly effective in Mdr2 (Abcb4) knockout mice, a model for studying the disease.
The superior efficacy of 24-norursodeoxycholic acid compared to Ursodeoxycholic acid in treating sclerosing cholangitis highlights its potential as a more effective treatment option for patients suffering from this debilitating condition. Its chemical properties, including its off-white to pale yellow solid appearance, contribute to its stability and suitability for pharmaceutical applications.

InChI:InChI=1/C23H38O4/c1-13(10-20(26)27)16-4-5-17-21-18(7-9-23(16,17)3)22(2)8-6-15(24)11-14(22)12-19(21)25/h13-19,21,24-25H,4-12H2,1-3H3,(H,26,27)/t13-,14+,15-,16-,17+,18+,19+,21+,22+,23-/m1/s1

Upstream product

• 128-13-2 ursodeoxycholic acid 
• 6058-15-7 (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid 
• 118316-07-7 3α,7β-diformyloxy-24-nor-5β-cholan-23-nitrile 
• 118316-12-4 3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile 
• 1380159-64-7 3α,7β-dihydroxy-24-nor-5β-cholan-23-oic acid potassium salt 

Downstream Products

• 141417-57-4 23-p-toluenesulfoxy-24-nor-5β-cholane-3α,7β-diol 
• 141541-00-6 sodium 3α,7β-dihydroxy-24-nor-5β-cholane-23-sulfonate 

Relevant academic research and scientific papers

CHOLANE DERIVATIVES FOR USE IN THE TREATMENT AND/OR PREVENTION OF FXR AND TGR5/GPBAR1 MEDIATED DISEASES

13073PTWO 56 ABSTRACT The present invention relates to compounds having cholane scaffolds of formula (I), said compounds for use in the treatment and/or prevention of FXR and TGR5/GPBAR1 mediated diseases. 5

Modification on ursodeoxycholic acid (UDCA) scaffold. Discovery of bile acid derivatives as selective agonists of cell-surface G-protein coupled bile acid receptor 1 (GP-BAR1)

Bile acids are signaling molecules interacting with the nuclear receptor FXR and the G-protein coupled receptor 1 (GP-BAR1/TGR5). GP-BAR1 is a promising pharmacological target for the treatment of steatohepatitis, type 2 diabetes, and obesity. Endogenous bile acids and currently available semisynthetic bile acids are poorly selective toward GP-BAR1 and FXR. Thus, in the present study we have investigated around the structure of UDCA, a clinically used bile acid devoid of FXR agonist activity, to develop a large family of side chain modified 3,7 dihydroxyl cholanoids that selectively activate GP-BAR1. In vivo and in vitro pharmacological evaluation demonstrated that administration of compound 16 selectively increases the expression of pro-glucagon 1, a GP-BAR1 target, in the small intestine, while it had no effect on FXR target genes in the liver. Further, compound 16 results in a significant reshaping of bile acid pool in a rodent model of cholestasis. These data demonstrate that UDCA is a useful scaffold to generate novel and selective steroidal ligands for GP-BAR1.

OPTIMIZED SYNTHESIS OF PURE, NON-POLYMORPHIC, CRYSTALLINE BILE ACIDS WITH DEFINED PARTICLE SIZE

The present invention relates to a pure polymorph of Nor-UDCA or Bis-nor-UDCA, or of a pharmaceutically acceptable salt thereof. The invention further provides a pharmaceutical composition comprising the polymorph of the invention, and a method for preparing the polymorph. The invention includes the pharmaceutical use of the polymorph or of the pharmaceutical composition of the invention.

Optimized synthesis of pure, non-polymorphic, crystalline bile acids with defined particle size

The present invention relates to a pure polymorph of Nor-UDCA or Bis-nor-UDCA, or of a pharmaceutically acceptable salt thereof. The invention further provides a pharmaceutical composition comprising the polymorph of the invention, and a method for preparing the polymorph. The invention includes the pharmaceutical use of the polymorph or of the pharmaceutical composition of the invention.