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Remogliflozin Etabonate

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Chemistry

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Also known as: 442201-24-3, Gsk-189075, Gsk-189075a, Gsk189075a, Remogliflozin etabonate [inn], Tr0qt6qsul

Molecular Formula

C₂₆H₃₈N₂O₉

Molecular Weight

522.6 g/mol

InChI Key

UAOCLDQAQNNEAX-ABMICEGHSA-N

FDA UNII

TR0QT6QSUL

Remogliflozin Etabonate is an orally available prodrug of remogliflozin, a benzylpyrazole glucoside-based inhibitor of renal sodium-glucose co-transporter subtype 2 (SGLT2) with antihyperglycemic activity. Upon administration and absorption, the inactive prodrug is converted to its active form remogliflozin and acts selectively on the sodium-glucose co-transporter subtype 2 (SGLT2).

1 2D Structure

Remogliflozin Etabonate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-methyl-1-propan-2-yl-4-[(4-propan-2-yloxyphenyl)methyl]pyrazol-3-yl]oxyoxan-2-yl]methyl carbonate

2.1.2 InChI

InChI=1S/C26H38N2O9/c1-7-33-26(32)34-13-20-21(29)22(30)23(31)25(36-20)37-24-19(16(6)28(27-24)14(2)3)12-17-8-10-18(11-9-17)35-15(4)5/h8-11,14-15,20-23,25,29-31H,7,12-13H2,1-6H3/t20-,21-,22+,23-,25+/m1/s1

2.1.3 InChI Key

UAOCLDQAQNNEAX-ABMICEGHSA-N

2.1.4 Canonical SMILES

CCOC(=O)OCC1C(C(C(C(O1)OC2=NN(C(=C2CC3=CC=C(C=C3)OC(C)C)C)C(C)C)O)O)O

2.1.5 Isomeric SMILES

CCOC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=NN(C(=C2CC3=CC=C(C=C3)OC(C)C)C)C(C)C)O)O)O

2.2 Other Identifiers

2.2.1 UNII

TR0QT6QSUL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside

2.3.2 Depositor-Supplied Synonyms

1. 442201-24-3

2. Gsk-189075

3. Gsk-189075a

4. Gsk189075a

5. Remogliflozin Etabonate [inn]

6. Tr0qt6qsul

7. Ethyl (((2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-((4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazol-3-yl)oxy)tetrahydro-2h-pyran-2-yl)methyl) Carbonate

8. Ethyl [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[5-methyl-1-propan-2-yl-4-[(4-propan-2-yloxyphenyl)methyl]pyrazol-3-yl]oxyoxan-2-yl]methyl Carbonate

9. 5-methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside

10. Unii-tr0qt6qsul

11. Kgt-1681

12. Remogliflozin Etabonate [usan]

13. Beta-d-glucopyranoside, 5-methyl-4-((4-(1-methylethoxy)phenyl)methyl)-1-(1-methylethyl)-1h-pyrazol-3-yl, 6-(ethyl Carbonate)

14. Beta-d-glucopyranoside, 5-methyl-4-[[4-(1-methylethoxy)phenyl]methyl]-1-(1-methylethyl)-1h-pyrazol-3-yl, 6-(ethyl Carbonate)

15. S0993

16. Schembl721678

17. Chembl2028665

18. Dtxsid50963191

19. Chebi:177541

20. Gsk 189075a

21. Zinc3979756

22. Remogliflozin Etabonate (usan/inn)

23. Bdbm50559516

24. Gsk189075

25. Bhv-091009

26. Db12935

27. Remogliflozin Etabonate (gsk189075)

28. Remogliflozin Etabonate [who-dd]

29. Br162756

30. Hy-14945

31. Cs-0003650

32. D10055

33. Q7312052

34. 3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-1-isopropyl-5-methylpyrazole

35. 3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole

36. 4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazole-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside

37. 5-methyl-1-(propan-2-yl)-4-((4-((propan-2-yl)oxy)phenyl)methyl)-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-.beta.-d-glucopyranoside

38. 5-methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1h-pyrazol-3-yl 6-o- (ethoxycarbonyl)-.beta.-d-glucopyranoside

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₈N₂O₉
Molecular Weight	522.6 g/mol
XLogP3	3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	522.25773079 g/mol
Monoisotopic Mass	522.25773079 g/mol
Topological Polar Surface Area	142 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	704
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.)

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