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147254-64-6

147254-64-6

Synopsis, Chemistry

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Also known as: 147254-64-6, As-3201, Ranirestat [inn], Z26p56gftv, Chembl334830, (3r)-2'-[(4-bromo-2-fluorophenyl)methyl]spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetrone

Molecular Formula

C₁₇H₁₁BrFN₃O₄

Molecular Weight

420.2 g/mol

InChI Key

QCVNMNYRNIMDKV-QGZVFWFLSA-N

FDA UNII

Z26P56GFTV

Ranirestat is a structurally novel and stereospecifically potent aldose reductase (AKR1B; EC 1.1.1.21) inhibitor, which contains a succinimide ring that undergoes ring-opening at physiological pH levels. It has been used in trials studying the treatment of Mild to Moderate Diabetic Sensorimotor Polyneuropathy.

1 2D Structure

147254-64-6

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R)-2'-[(4-bromo-2-fluorophenyl)methyl]spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetrone

2.1.2 InChI

InChI=1S/C17H11BrFN3O4/c18-10-4-3-9(11(19)6-10)8-21-14(24)12-2-1-5-22(12)17(16(21)26)7-13(23)20-15(17)25/h1-6H,7-8H2,(H,20,23,25)/t17-/m1/s1

2.1.3 InChI Key

QCVNMNYRNIMDKV-QGZVFWFLSA-N

2.1.4 Canonical SMILES

C1C(=O)NC(=O)C12C(=O)N(C(=O)C3=CC=CN23)CC4=C(C=C(C=C4)Br)F

2.1.5 Isomeric SMILES

C1C(=O)NC(=O)[C@@]12C(=O)N(C(=O)C3=CC=CN23)CC4=C(C=C(C=C4)Br)F

2.2 Other Identifiers

2.2.1 UNII

Z26P56GFTV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo(1,2-a)pyrazine-4-spiro-3'-pyrrolidine-1.2',3,5'-tetrone

2. As 3201

3. As-3201

4. Sx 3030

5. Sx 3202

6. Sx-3030

7. Sx-3202

2.3.2 Depositor-Supplied Synonyms

1. 147254-64-6

2. As-3201

3. Ranirestat [inn]

4. Z26p56gftv

5. Chembl334830

6. (3r)-2'-[(4-bromo-2-fluorophenyl)methyl]spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetrone

7. Sx-3030

8. (3r)-2'-(4-bromo-2-fluorobenzyl)spiro(pyrrolidine-3,4'(1'h)-pyrrolo(1,2-a)pyrazine)-1',2,3',5(2'h)-tetrone

9. (r)-2'-(4-bromo-2-fluorobenzyl)-1'h-spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'h)-tetraone

10. Unii-z26p56gftv

11. C17h11brfn3o4

12. Raniestat

13. As 3201

14. Sx 3201

15. Ranirestat (jan/inn)

16. Ranirestat [jan]

17. Ranirestat [who-dd]

18. Schembl498993

19. Ranirestat, >=97% (hplc)

20. Dtxsid80163642

21. Zinc598422

22. Bcp14386

23. Bdbm50067407

24. Db05327

25. Sb17385

26. Sx-3201

27. Ncgc00484081-01

28. (r)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo(1,2-a)pyrazine-4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone

29. 2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo(1,2-a)pyrazine-4-spiro-3'-pyrrolidine-1.2',3,5'-tetrone

30. Hy-15314

31. A13523

32. D06403

33. A901889

34. Q7293074

35. (3r)-2''-(4-bromo-2-fluorobenzyl)-1''h,2h,5h-spiro[pyrrolidine-3,4''-pyrrolo[1,2-a]pyrazine]-1'',2,3'',5(2''h)-tetrone

36. (3r)-2-(4-bromo-2-fluorobenzyl)spiro(pyrrolidine-3,4(1h)-pyrrolo(1,2-a)pyrazine)-1,2,3,5(2h)-tetrone

37. (r)-2-(4-bromo-2-fluorobenzyl)-1h-spiro[pyrrolidine-3,4-pyrrolo[1,2-a]pyrazine]-1,2,3,5(2h)-tetraone

38. Spiro(pyrrolidine-3,4'(1'h)-pyrrolo(1,2-a)pyrazine)-1',2,3',5(2'h)-tetrone, 2'-((4-bromo-2-fluorophenyl)methyl)-, (-)-

39. Spiro(pyrrolidine-3,4'(1'h)-pyrrolo(1,2-a)pyrazine)-1',2,3',5(2'h)-tetrone, 2'-((4-bromo-2-fluorophenyl)methyl)-, (3'r)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₁BrFN₃O₄
Molecular Weight	420.2 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	418.99170 g/mol
Monoisotopic Mass	418.99170 g/mol
Topological Polar Surface Area	88.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	689
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

Investigated for use/treatment in neuropathy (diabetic).

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

5.2 Mechanism of Action

Ranirestat alleviates diabetic neuropathy, a complication of diabetes, by inhibiting aldose reductase and thereby inhibiting the accumulation of intracellular sorbitol that causes diabetic neuropathy. This drug has a stronger inhibitory effect and is longer acting compared to other drugs in this therapeutic area. Ranirestat showed good penetration into the nerve tissue, resulting in dose-dependent inhibition of intraneural accumulation of sorbitol and fructose in a clinical study.