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    Ranirestat

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 420.2 g/mol
    Molecular Formula C17H11BrFN3O4
    XLogP31.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass418.99170 g/mol
    Monoisotopic Mass418.99170 g/mol
    Topological Polar Surface Area88.5 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity689
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.