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Tofogliflozin

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Chemistry

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Also known as: 903565-83-3, Csg 452, Tofogliflozin [inn], Tofogliflozin anhydrous, Csg-452, (3s,3'r,4's,5's,6'r)-5-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)spiro[1h-2-benzofuran-3,2'-oxane]-3',4',5'-triol

Molecular Formula

C₂₂H₂₆O₆

Molecular Weight

386.4 g/mol

InChI Key

VWVKUNOPTJGDOB-BDHVOXNPSA-N

FDA UNII

554245W62T

Tofogliflozin has been used in trials studying the treatment and prevention of Diabetes Mellitus Type 2.

1 2D Structure

Tofogliflozin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,3'R,4'S,5'S,6'R)-5-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol

2.1.2 InChI

InChI=1S/C22H26O6/c1-2-13-3-5-14(6-4-13)9-15-7-8-16-12-27-22(17(16)10-15)21(26)20(25)19(24)18(11-23)28-22/h3-8,10,18-21,23-26H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22+/m1/s1

2.1.3 InChI Key

VWVKUNOPTJGDOB-BDHVOXNPSA-N

2.1.4 Canonical SMILES

CCC1=CC=C(C=C1)CC2=CC3=C(COC34C(C(C(C(O4)CO)O)O)O)C=C2

2.1.5 Isomeric SMILES

CCC1=CC=C(C=C1)CC2=CC3=C(CO[C@@]34[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C2

2.2 Other Identifiers

2.2.1 UNII

554245W62T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-((4-ethylphenyl)methyl)-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)spiro(isobenzofuran-1(3h),2'-(2h)pyran)-3',4',5'-triol

2. Apleway

3. Csg452

4. Deberza

5. Tofogliflozin Anhydrous

6. Tofogliflozin Hydrate

2.3.2 Depositor-Supplied Synonyms

1. 903565-83-3

2. Csg 452

3. Tofogliflozin [inn]

4. Tofogliflozin Anhydrous

5. Csg-452

6. (3s,3'r,4's,5's,6'r)-5-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)spiro[1h-2-benzofuran-3,2'-oxane]-3',4',5'-triol

7. R-7201

8. 903565-83-3 (free)

9. 554245w62t

10. (1s,3'r,4's,5's,6'r)-6-(4-ethylbenzyl)-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3h-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

11. Spiro(isobenzofuran-1(3h),2'-(2h)pyran)-3',4',5'-triol,6-((4-ethylphenyl)methyl)-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-,(1s,3'r,4's,5's,6'r)-

12. Apleway

13. Deberza

14. Tofogliflozin Anyhydrous

15. Ro4998452

16. Ro-4998452

17. Unii-554245w62t

18. Tofogliflozin [mi]

19. Ec 619-989-0

20. Schembl903156

21. Tofogliflozin [who-dd]

22. Gtpl9395

23. Chembl2110731

24. Csg452;csg-452

25. Dtxsid90238097

26. Chebi:136041

27. Bdbm50396779

28. Zinc35826342

29. Db11824

30. Compound 16d [pmid: 22889351]

31. Ncgc00485920-01

32. Ac-31468

33. Q27261271

34. (1s,3'r,4's,5's,6'r)-6-((4-ethylphenyl)methyl)-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro(isobenzofuran-1(3h), 2'-(2h)pyran)-3',4',5'-triol

35. (1s,3'r,4's,5's,6'r)-6-((4-ethylphenyl)methyl)-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3h-spiro(2-benzofuran-1,2'-pyran)-3',4',5'-triol

2.4 Create Date

2010-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₆O₆
Molecular Weight	386.4 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	386.17293854 g/mol
Monoisotopic Mass	386.17293854 g/mol
Topological Polar Surface Area	99.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	521
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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