U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H11BrFN3O4
Molecular Weight 420.189
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RANIRESTAT

SMILES

FC1=C(CN2C(=O)C3=CC=CN3[C@@]4(CC(=O)NC4=O)C2=O)C=CC(Br)=C1

InChI

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

HIDE SMILES / InChI

Molecular Formula C17H11BrFN3O4
Molecular Weight 420.189
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ranirestat (AS-3201, SX-3030, SX-3202) is an oral aldose reductase inhibitor. (-)-enantiomer (AS-3201) is 10 times more potent in inhibition of the aldose reductase and 500 times more potent in the in vivo activity than the corresponding (+)-enantiomer (SX-3202). Ranirestat is being developed by Dainippon Sumitomo Pharma (formerly Dainippon Pharmaceutical) for the treatment of diabetic complications, primarily diabetic neuropathy. Ranirestat is a well-tolerated front-line inhibitor. It reproducibly exhibits some degree of measurable objective beneficial outcomes in diabetic neuropathy.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
15.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3213 ng/mL
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
3016 ng/mL
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
3644 ng/mL
40 mg single, oral
RANIRESTAT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
60.4 μg × h/mL
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
67 μg × h/mL
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
71.1 μg × h/mL
40 mg single, oral
RANIRESTAT plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
105.6 h
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
131.6 h
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
133.7 h
40 mg single, oral
RANIRESTAT plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.665%
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
1.03%
40 mg single, oral
RANIRESTAT plasma
Homo sapiens
0.77%
40 mg single, oral
RANIRESTAT plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
10-80 mg/day for several weeks to months
Route of Administration: Oral
In Vitro Use Guide
High glucose significantly increased sorbitol levels, superoxide generation and vascular cell adhesion molecule-1 mRNA levels in, and THP-1 cell adhesion to, human umbilical vein endothelial cells, all of which were prevented by 500 nM ranirestat
Substance Class Chemical
Record UNII
Z26P56GFTV
Record Status Validated (UNII)
Record Version