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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClO5S
Molecular Weight 424.938
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOTAGLIFLOZIN

SMILES

CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)[C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)C=C1

InChI

InChIKey=QKDRXGFQVGOQKS-CRSSMBPESA-N
InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1

HIDE SMILES / InChI

Description

Sotagliflozin (LX4211) is an orally-delivered small molecule compound that is currently in development for the treatment of type 1 and type 2 diabetes mellitus. Sotagliflozin (LX4211) inhibits both sodium-glucose cotransporter type 2, or SGLT2, a transporter responsible for most of the glucose reabsorption performed by the kidney, and sodium-glucose cotransporter type 1, or SGLT1, a transporter responsible for glucose and galactose absorption in the gastrointestinal tract, and to a lesser extent than SGLT2, glucose reabsorption in the kidney. Combining SGLT1 and SGLT2 inhibition in a single molecule would provide complementary insulin-independent mechanisms to treat diabetes.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
36.0 nM [IC50]
1.8 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SOTAGLIFLOZIN
Primary
SOTAGLIFLOZIN

Cmax

ValueDoseCo-administeredAnalytePopulation
274 ng/mL
400 mg 1 times / day multiple, oral
SOTAGLIFLOZIN plasma
Homo sapiens
180 ng/mL
400 mg 1 times / day multiple, oral
SOTAGLIFLOZIN plasma
Homo sapiens
291 ng/mL
300 mg 1 times / day steady-state, oral
SOTAGLIFLOZIN plasma
Homo sapiens
113 ng/mL
150 mg 1 times / day steady-state, oral
SOTAGLIFLOZIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2879 ng × h/mL
400 mg 1 times / day multiple, oral
SOTAGLIFLOZIN plasma
Homo sapiens
2213 ng × h/mL
400 mg 1 times / day multiple, oral
SOTAGLIFLOZIN plasma
Homo sapiens
1752 ng × h/mL
300 mg 1 times / day steady-state, oral
SOTAGLIFLOZIN plasma
Homo sapiens
732 ng × h/mL
150 mg 1 times / day steady-state, oral
SOTAGLIFLOZIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
18.1 h
400 mg 1 times / day multiple, oral
SOTAGLIFLOZIN plasma
Homo sapiens
16.6 h
400 mg 1 times / day multiple, oral
SOTAGLIFLOZIN plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
Sotagliflozin (LX4211) at 400 mg once daily for 7 days.
Route of Administration: Oral
In Vitro Use Guide
The ability of sotagliflozin in vitro to inhibit sodium-dependent glucose transporters 1 and 2 (SGLT1 and SGLT2) was established. Sotagliflozin inhibited SGLT2 with an IC50 of 0.0018 uΜ, and it inhibited SGLT1 with an IC50 of 0.036 uM.