319426-57-8

Basic information

• Product Name: DEXAMETHASONE 21-O-BETA-D-GALACTOPYRANOSIDE
• Synonyms: DEXAMETHASONE 21-O-BETA-D-GALACTOPYRANOSIDE
• CAS NO: 319426-57-8
• Molecular Formula: C28H40O10
• Molecular Weight: 536.61
• Mol File: 319426-57-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 782.634°C at 760 mmHg
• Flash Point: 257.57°C
• Appearance: /
• Density: 1.427g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: DEXAMETHASONE 21-O-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DEXAMETHASONE 21-O-BETA-D-GALACTOPYRANOSIDE(319426-57-8)
• EPA Substance Registry System: DEXAMETHASONE 21-O-BETA-D-GALACTOPYRANOSIDE(319426-57-8)

Safety Data

• Hazardous Substances Data: 319426-57-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H40O10/c1-13-8-17-16-5-4-14-9-15(30)6-7-26(14,2)21(16)18(31)10-27(17,3)28(13,36)20(32)12-37-25-24(35)23(34)22(33)19(11-29)38-25/h6-7,9,13,16-19,21-25,29,31,33-36H,4-5,8,10-12H2,1-3H3/t13-,16+,17+,18+,19-,21-,22+,23+,24-,25-,26+,27+,28+/m1/s1

Upstream product

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 50-02-2 dexamethasone 
• 92901-30-9 9α-fluoro-11β,17α-dihydroxy-16α-methyl-3,20-dioxopregna-1,4-dien-21-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 88158-45-6 9α-fluoro-11β,17α-dihydroxy-16α-methyl-3,20-dioxapregna-1,4-dien-21-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Compositions and methods for targeted enzymatic release of cell regulatory compounds

Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.

A Colon-Specific Drug-Delivery System Based on Drug Glycosides and the Glycosidases of Colonic Bacteria

Steroid glycosides and the unique glycosidase activity of the colonic microflora form the basis of a new-colon-specific drug-delivery system.Drug glycosides are hydrophilic and, thus, poorly absorbed from the small intestine.Once such a glycoside reaches the colon it can be cleaved by bacterial glycosidases, releasing the free drug to be absorbed by the colonic mucosa.This concept was illustrated with dexamethasone 21-β-D-glucoside (1) and prednisolone 21-β-D-glucoside (2), two prodrugs that may be useful in treating inflammatory bowel disease.Hydrolysis of theprodrugs by β-glucosidase and fecal homogenates in vitro released the free steroids.Glucosides 1 and 2 were administered to rats intragastrically to determine when when and where the free steroids were released.Unmodified dexamethasone (3) and prednisolone (4) were also given to rats intragastrically to compare absorption of the glucosides with the free steroids.Both glucosides were found to reach the rat lower intestine in 4-5 h, where they were rapidly hydrolyzed, releasing the free steroids.Delivery of steroid 3 (via glucoside 1) was more specific than that of steroid 4 (via glucoside 2): nearly 60percent of an oral dose of glucoside 1 reached the cecum, whereas less than 15percent of glucoside 2 reached the cecum.When free steroids 3 and 4 were administered orally, they were almost exclusively absorbed in the small intestine: less than 1percent of an oral dose of each reached the cecum.