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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

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