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| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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≥96% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Ranirestat (AS-3201) potent and orally active aldose reductase (AR) inhibitor with IC 50 s of 11 nM and 15 nM for rat lens AR and recombinant human AR , respectively, and a K i of 0.38 nM for recombinant human AR . Ranirestat has the potential for diabetic sensorimotor polyneuropathy treatment. Ranirestat also has a neuroprotective effect on diabetic retinas
In Vitro
Ranirestat concentration-dependently inhibits sorbitol accumulation in rat erythrocytes and sciatic nerves incubated in the high concentration (500 mg/dl) of glucose. The potency of Ranirestat inhibition of sorbitol accumulation is similar between rat erythrocytes and sciatic nerves with IC 50 values of 0.010 μM and 0.041 μM, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Ranirestat (0.03-1.0 mg/kg; oral administration; once daily; for 3 weeks; male STD-Wistar rats) treatment dose-dependently decreases the elevated sorbitol and fructose levels in the rat sciatic nerves without affecting blood glucose level. Ranirestat also improves the STZ-induced decrease in motor nerve conduction velocity (MNCV) in a dose-dependent manner . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male STD-Wistar rats aged about (12-week-old; 260-290 g) injected with Streptozotocin (STZ) Dosage: 0.03 mg/kg, 0.1 mg/kg, 0.3 mg/kg, 1 mg/kg Administration: Oral administration; once daily; for 3 weeks Result: Dose-dependently decreased the elevated sorbitol and fructose levels in the rat sciatic nerves without affecting blood glucose level.
Form:Solid
IC50& Target:IC50: 11 nM (Rat lens aldose reductase) and 15 nM (Recombinant humanaldose reductase), Ki: 0.38 nM (Recombinant humanaldose reductase)
| Canonical Smiles | C1C(=O)NC(=O)C12C(=O)N(C(=O)C3=CC=CN23)CC4=C(C=C(C=C4)Br)F |
|---|---|
| IUPAC Name | (3R)-2'-[(4-bromo-2-fluorophenyl)methyl]spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetrone |
| InChIKey | QCVNMNYRNIMDKV-QGZVFWFLSA-N |
| 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 |
| Isomeric SMILES | C1C(=O)NC(=O)[C@@]12C(=O)N(C(=O)C3=CC=CN23)CC4=C(C=C(C=C4)Br)F |
| Alternate CAS | 147254-64-6 |
| PubChem CID | 153948 |
| MeSH Entry Terms | 2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo(1,2-a)pyrazine-4-spiro-3'-pyrrolidine-1.2',3,5'-tetrone;AS 3201;AS-3201;ranirestat;SX 3030;SX 3202;SX-3030;SX-3202 |
| Molecular Weight | 420.19 |
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Halobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Fluorobenzenes |
| Alternative Parents | Bromobenzenes Pyrrolidine-2-ones Aryl bromides Aryl fluorides N-substituted carboxylic acid imides Pyrroles Dicarboximides N-unsubstituted carboxylic acid imides Heteroaromatic compounds Lactams Azacyclic compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Organobromides Organofluorides Organonitrogen compounds Organopnictogen compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Bromobenzene - Fluorobenzene - Aryl bromide - Aryl fluoride - Aryl halide - 2-pyrrolidone - Pyrrolidone - Carboxylic acid imide, n-substituted - Carboxylic acid imide - Heteroaromatic compound - Dicarboximide - Pyrrolidine - Pyrrole - Carboxylic acid imide, n-unsubstituted - Lactam - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organopnictogen compound - Organofluoride - Organohalogen compound - Organobromide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring. |
| External Descriptors | Not available |
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| Solubility | DMSO : ≥ 50 mg/mL (118.99 mM) |
|---|---|
| Molecular Weight | 420.200 g/mol |
| XLogP3 | 1.300 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Exact Mass | 418.992 Da |
| Monoisotopic Mass | 418.992 Da |
| Topological Polar Surface Area | 88.500 Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 689.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |