LX-4211 Chemical Properties

Boiling point:

607.9±55.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMSO:84.0(Max Conc. mg/mL);197.67(Max Conc. mM)
Ethanol:17.0(Max Conc. mg/mL);40.01(Max Conc. mM)

pka

12.87±0.70(Predicted)

form 

Powder

color 

White to off-white

LX-4211 Usage And Synthesis

Uses

Sotagliflozin is used for the treatment of patients with type 1 diabetes mellitus.

Clinical Use

Two of the current SGLT-2 inhibitors (canagliflozin and LX-4211) have effects on SGLT-1. LX-4211 is a dual SGLT1/2 inhibitor and higher doses of canagliflozin transiently inhibit SGLT-1 in the gut due to high canagliflozin concentrations within the intestinal lumen during the period of drug absorption.

Synthesis

Sotagliflozin is a dual SGLT-1/SGLT-2 inhibitor which is currently under development by Lexicon Pharmaceuticals (phase III). It follows a similar strategy to ertugliflozin, i.e. aryl addition on an acyclic precursor. The synthesis starts from L-xylose 53, and the aryl moiety (same aryl moiety as for dapagliflozin) is introduced on an amide derivative (morpholine amide 54) via Grignard addition. A subsequent transformation leads to the sotagliflozin (Scheme 10). The overall yield of the synthesis is around 30%.

Sotagliflozin synthesis

LX-4211(1018899-04-1)Related Product Information

• Dapagliflozin
• Empagliflozin
• D-Glucitol, 1,5-dideoxy-1,5-epithio-1-C-[5-[(4-ethoxyphenyl)Methyl]-2-Methoxy-4-Methylphenyl]-, (1S)-
• Tofogliflozin
• Ipragliflozin
• Canagliflozin