sotagliflozin   Click here for help

GtoPdb Ligand ID: 8312

Synonyms: Inpefa® | LX-4211 | LX4211 | Zynquista®
Approved drug
sotagliflozin is an approved drug (EMA (2019), FDA (2023))
Compound class: Synthetic organic
Comment: Sotagliflozin is a dual inhibitor of the sodium/glucose cotransporters 1 and 2 (SGLT1/2) [5,8]. SGLT1 and SGLT2 mediate glucose reabsorption, by the kidney and in the gastrointestinal tract respectively.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 104.45
Molecular weight 424.11
XLogP 3.9
No. Lipinski's rules broken 0
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Canonical SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)C1OC(SC)C(C(C1O)O)O
Isomeric SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)[C@@H]1O[C@H](SC)[C@H]([C@@H]([C@H]1O)O)O
InChI 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
1. Aziri B, Begic E, Jankovic S, Mladenovic Z, Stanetic B, Kovacevic-Preradovic T, Iglica A, Mujakovic A. (2023)
Systematic review of sodium-glucose cotransporter 2 inhibitors: a hopeful prospect in tackling heart failure-related events.
ESC Heart Fail, 10 (3): 1499-1530. [PMID:36967133]
2. Banerjee M, Pal R, Nair K, Mukhopadhyay S. (2023)
SGLT2 inhibitors and cardiovascular outcomes in heart failure with mildly reduced and preserved ejection fraction: A systematic review and meta-analysis.
Indian Heart J, 75 (2): 122-127. [PMID:36914068]
3. Bhatt DL, Szarek M, Pitt B, Cannon CP, Leiter LA, McGuire DK, Lewis JB, Riddle MC, Inzucchi SE, Kosiborod MN et al.. (2021)
Sotagliflozin in Patients with Diabetes and Chronic Kidney Disease.
N Engl J Med, 384 (2): 129-139. [PMID:33200891]
4. Bhatt DL, Szarek M, Steg PG, Cannon CP, Leiter LA, McGuire DK, Lewis JB, Riddle MC, Voors AA, Metra M et al.. (2021)
Sotagliflozin in Patients with Diabetes and Recent Worsening Heart Failure.
N Engl J Med, 384 (2): 117-128. [PMID:33200892]
5. Lapuerta P, Zambrowicz B, Strumph P, Sands A. (2015)
Development of sotagliflozin, a dual sodium-dependent glucose transporter 1/2 inhibitor.
Diab Vasc Dis Res, 12 (2): 101-10. [PMID:25690134]
6. Rodriguez R, Kaluzna SD. (2023)
Sodium-glucose cotransporter 2 inhibitors and cardiovascular clinical outcomes in acute heart failure: A narrative review.
Am J Health Syst Pharm, 80 (13): 818-826. [PMID:36971375]
7. Verma S, Bhatt DL, Dhingra NK, Steg PG, Szarek M, Davies M, Metra M, Lund LH, Pitt B, SOLOIST Investigators. (2023)
Time to Benefit With Sotagliflozin in Patients With Worsening Heart Failure.
J Am Coll Cardiol, 81 (15): 1546-1549. [PMID:37045523]
8. Zambrowicz B, Freiman J, Brown PM, Frazier KS, Turnage A, Bronner J, Ruff D, Shadoan M, Banks P, Mseeh F et al.. (2012)
LX4211, a dual SGLT1/SGLT2 inhibitor, improved glycemic control in patients with type 2 diabetes in a randomized, placebo-controlled trial.
Clin Pharmacol Ther, 92 (2): 158-69. [PMID:22739142]