LX-4211 CAS 1018899-04-1

Introduction：Basic information about LX-4211 CAS 1018899-04-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

LX-4211 Basic information

• Product Name: LX-4211
• Synonyms: (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol;CS-1853;LX4211; LX 4211; LX4211; LX 4211;LX-4211;(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(Methylthio)tetrahydro-2H-pyran-3,4,5-triol;(5S)-Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-beta-L-xylopyranoside;Sotagliflozin;LX4211/LX-4211
• CAS: 1018899-04-1
• MF: C21H25ClO5S
• MW: 424.94
• Mol File: 1018899-04-1.mol

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
• Optical Rotation: 35.7°(C=0.01g/mL, CHCL3, 20°C, 589nm)
• InChIKey: QKDRXGFQVGOQKS-WFCPIQDQNA-N
• SMILES: [C@@H]1(C2=CC=C(Cl)C(CC3=CC=C(OCC)C=C3)=C2)O[C@H](SC)[C@@H](O)[C@H](O)[C@H]1O |&1:0,19,22,24,26,r|

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

IC 50

SGLT1; SGLT2