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Sotagliflozin

Sotagliflozin

Synopsis, Chemistry

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Also known as: 1018899-04-1, Lx-4211, Lx4211, Lp-802034, (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol, 6b4zbs263y

Molecular Formula

C₂₁H₂₅ClO₅S

Molecular Weight

424.9 g/mol

InChI Key

QKDRXGFQVGOQKS-CRSSMBPESA-N

FDA UNII

6B4ZBS263Y

Sotagliflozin is an orally bioavailable inhibitor of the sodium-glucose co-transporter subtype 1 (SGLT1) and 2 (SGLT2), with potential antihyperglycemic activity. Upon oral administration, sotagliflozin binds to and blocks both SGLT1 in the gastrointestinal (GI) tract and SGLT2 in the kidneys, thereby suppressing the absorption of glucose from the GI tract and the reabsorption of glucose by the proximal tubule into the bloodstream, respectively. This decreases glucose uptake and enhances the urinary excretion of glucose, which lowers and/or normalizes blood glucose levels. SGLT1 is the primary transporter responsible for glucose absorption from the GI tract. SGLT2, a transport protein exclusively expressed in the proximal renal tubules, mediates approximately 90% of renal glucose reabsorption from tubular fluid.

1 2D Structure

Sotagliflozin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol

2.1.2 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

2.1.3 InChI Key

QKDRXGFQVGOQKS-CRSSMBPESA-N

2.1.4 Canonical SMILES

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)SC)O)O)O)Cl

2.1.5 Isomeric SMILES

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)SC)O)O)O)Cl

2.2 Other Identifiers

2.2.1 UNII

6B4ZBS263Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol

2. Lx-4211

3. Lx4211

2.3.2 Depositor-Supplied Synonyms

1. 1018899-04-1

2. Lx-4211

3. Lx4211

4. Lp-802034

5. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol

6. 6b4zbs263y

7. Sar439954

8. Sar-439954

9. (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol

10. Zynquista

11. Beta-l-xylopyranoside, Methyl 5-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-, (5s)-

12. Sotagliflozin [usan:inn]

13. Unii-6b4zbs263y

14. Beta-l-xylopyranoside, Methyl 5-c-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-, (5s)-

15. Mfcd22493506

16. Lx 4211

17. Lp 802034

18. Sotagliflozin [mi]

19. Sotagliflozin (lx4211)

20. Sotagliflozin [inn]

21. Sotagliflozin (usan/inn)

22. Sotagliflozin [usan]

23. Sotagliflozin (lx-4211)

24. Sotagliflozin [who-dd]

25. Gtpl8312

26. Schembl1038287

27. Chembl3039507

28. Dtxsid20144314

29. Amy12393

30. Ex-a1167

31. Bdbm50235017

32. S8103

33. Zinc95641922

34. Akos025290846

35. Ccg-268940

36. Cs-1069

37. Db12713

38. Ac-29890

39. As-35202

40. Bl161424

41. Hy-15516

42. D10669

43. A852129

44. Q27088840

45. (2s,3r,4r,5s,6r)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-tetrahydro-6-(methylthio)-2h-pyran-3,4,5-triol;lx4211

46. (2s,3r,4r,5s,6r)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2h-pyran-3,4,5-triol

47. .beta.-l-xylopyranoside, Methyl 5-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-, (5s)-

48. Methyl (5s)-5-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-.beta.-l-xylopyranoside

2.4 Create Date

2008-07-07

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅ClO₅S
Molecular Weight	424.9 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	424.1111228 g/mol
Monoisotopic Mass	424.1111228 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	476
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Zynquista is indicated as an adjunct to insulin therapy to improve glycaemic control in adults with type 1 diabetes mellitus with a Body Mass Index (BMI) 27 kg/m2, who have failed to achieve adequate glycaemic control despite optimal insulin therapy.

Treatment of type II diabetes mellitus

Treatment of type I diabetes mellitus

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Sodium-Glucose Transporter 2 Inhibitors

Compounds that inhibit SODIUM-GLUCOSE TRANSPORTER 2. They lower blood sugar by preventing the reabsorption of glucose by the kidney and are used in the treatment of TYPE 2 DIABETES MELLITUS. (See all compounds classified as Sodium-Glucose Transporter 2 Inhibitors.)

5.2 ATC Code

A10

A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10B - Blood glucose lowering drugs, excl. insulins

A10BK - Sodium-glucose co-transporter 2 (sglt2) inhibitors

A10BK06 - Sotagliflozin