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Ipragliflozin

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Chemistry

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Also known as: 761423-87-4, Suglat, Asp-1941, Asp1941, Ipragliflozin [inn], (2s,3r,4r,5s,6r)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

Molecular Formula

C₂₁H₂₁FO₅S

Molecular Weight

404.5 g/mol

InChI Key

AHFWIQIYAXSLBA-RQXATKFSSA-N

FDA UNII

3N2N8OOR7X

Ipragliflozin is under investigation in Type 2 Diabetes and Diabetes Mellitus, Type 2.

1 2D Structure

Ipragliflozin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

2.1.2 InChI

InChI=1S/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/m1/s1

2.1.3 InChI Key

AHFWIQIYAXSLBA-RQXATKFSSA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)C=C(S2)CC3=C(C=CC(=C3)C4C(C(C(C(O4)CO)O)O)O)F

2.1.5 Isomeric SMILES

C1=CC=C2C(=C1)C=C(S2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)F

2.2 Other Identifiers

2.2.1 UNII

3N2N8OOR7X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (1s)-1,5-anhydro-1-(3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl)-d-glucitol

2. Asp-1941

3. Asp1941

4. Suglat

2.3.2 Depositor-Supplied Synonyms

1. 761423-87-4

2. Suglat

3. Asp-1941

4. Asp1941

5. Ipragliflozin [inn]

6. (2s,3r,4r,5s,6r)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

7. Ipragliflozin (asp1941)

8. 3n2n8oor7x

9. Chembl2018096

10. (1s)-1,5-anhydro-1-c-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-d-glucitol

11. Ipragliflozin (inn)

12. (1s)-1,5-anhydro-1-c-(3-((1-benzothiophen-2-yl)methyl)-4-fluorophenyl)-d-glucitol

13. Asp 1941

14. Unii-3n2n8oor7x

15. Ipragliflozin-l-proline

16. Ipragliflozin [mi]

17. (2s,3r,4r,5s,6r)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

18. Schembl337645

19. Ipragliflozin [who-dd]

20. Gtpl9394

21. Chebi:134724

22. Dtxsid701032738

23. Amy38779

24. Ex-a2770

25. Bdbm50381554

26. Mfcd19443744

27. S8637

28. Zinc38897728

29. Akos025405258

30. Ccg-268693

31. Db11698

32. Ncgc00378606-02

33. Ac-29008

34. As-39358

35. Hy-14894

36. D10196

37. Q17193526

38. (1s)-1,5-anhydro-1-(3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl)-d-glucitol

39. (1s)-1,5-anhydro-1-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-d-glucitol

40. (1s)-1,5-anhydro-1-c-[3-(1-benzothiophene-2-ylmethyl)-4-fluorophenyl]-d-glucitol

41. D-glucitol,1,5-anhydro-1-c-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-, (1s)-

42. (2s,3r,4r,5s,6r)-2-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-6-(hydroxymethyl)oxane-3,4,5-triol

43. D-glucitol, 1,5-anhydro-1-c-(3-(benzo(b)thien-2-ylmethyl)-4-fluorophenyl)-, (1s)-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₁FO₅S
Molecular Weight	404.5 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	404.10937310 g/mol
Monoisotopic Mass	404.10937310 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	525
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 Pharmacology and Biochemistry

4.1 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.)

4.2 ATC Code

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

A10BK05 - Ipragliflozin

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