Page last updated: 2024-12-08

as 3201

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

ranirestat: an aldose reductase inhibitor; AS-3201 and SX-3202 are the (R-(-))- and (S-(+))-isomers, respectively; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID153948
CHEMBL ID334830
SCHEMBL ID498993
MeSH IDM0296467

Synonyms (40)

Synonym
as-3201 ,
sx-3201
ranirestat
147254-64-6
ranirestat (jan/inn)
D06403
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
CHEMBL334830 ,
(3r)-2'-[(4-bromo-2-fluorophenyl)methyl]spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetrone
(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
bdbm50067407
z26p56gftv ,
spiro(pyrrolidine-3,4'(1'h)-pyrrolo(1,2-a)pyrazine)-1',2,3',5(2'h)-tetrone, 2'-((4-bromo-2-fluorophenyl)methyl)-, (-)-
unii-z26p56gftv
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)-
sx 3201
(r)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo(1,2-a)pyrazine-4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone
(3r)-2'-(4-bromo-2-fluorobenzyl)spiro(pyrrolidine-3,4'(1'h)-pyrrolo(1,2-a)pyrazine)-1',2,3',5(2'h)-tetrone
ranirestat [inn]
ranirestat [jan]
ranirestat [who-dd]
DB05327
SCHEMBL498993
HY-15314
DTXSID80163642
c17h11brfn3o4
AKOS030526562
ranirestat, >=97% (hplc)
NCGC00484081-01
(r)-2'-(4-bromo-2-fluorobenzyl)-1'h-spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'h)-tetraone
BCP14386
Q7293074
A13523
SB17385
(3r)-2-(4-bromo-2-fluorobenzyl)spiro(pyrrolidine-3,4(1h)-pyrrolo(1,2-a)pyrazine)-1,2,3,5(2h)-tetrone
(r)-2-(4-bromo-2-fluorobenzyl)-1h-spiro[pyrrolidine-3,4-pyrrolo[1,2-a]pyrazine]-1,2,3,5(2h)-tetraone
A901889
F85182
MS-27366

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" All adverse events were mild in severity."( Pharmacokinetics and Safety of Ranirestat in Patients With Hepatic Impairment.
Fujita, T; Inoue, K; Ishii, D; Itou, M; Kakuyama, H; Takagaki, T; Uchida, N, 2020
)
0.56

Pharmacokinetics

ExcerptReferenceRelevance
" An open-label, single-dose, parallel-group study was conducted to compare pharmacokinetic (PK) characteristics of an oral dose of ranirestat across subjects with normal hepatic function and patients with mild and moderate hepatic impairment because ranirestat is expected to be used by patients with diabetes mellitus, possibly including those with hepatic impairment."( Pharmacokinetics and Safety of Ranirestat in Patients With Hepatic Impairment.
Fujita, T; Inoue, K; Ishii, D; Itou, M; Kakuyama, H; Takagaki, T; Uchida, N, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B1Homo sapiens (human)IC50 (µMol)0.01500.00101.191310.0000AID309933
Aldo-keto reductase family 1 member B1Sus scrofa (pig)IC50 (µMol)0.01500.01500.61352.5000AID34668
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
retinoid metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
epithelial cell maturationAldo-keto reductase family 1 member B1Homo sapiens (human)
renal water homeostasisAldo-keto reductase family 1 member B1Homo sapiens (human)
carbohydrate metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
C21-steroid hormone biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
L-ascorbic acid biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
regulation of urine volumeAldo-keto reductase family 1 member B1Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
negative regulation of apoptotic processAldo-keto reductase family 1 member B1Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
fructose biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
cellular hyperosmotic salinity responseAldo-keto reductase family 1 member B1Homo sapiens (human)
metanephric collecting duct developmentAldo-keto reductase family 1 member B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B1Homo sapiens (human)
electron transfer activityAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glyceraldehyde oxidoreductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
L-glucuronate reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glycerol dehydrogenase [NADP+] activityAldo-keto reductase family 1 member B1Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
extracellular spaceAldo-keto reductase family 1 member B1Homo sapiens (human)
nucleoplasmAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID309933Inhibition of aldose reductase2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
Validation of an automated procedure for the prediction of relative free energies of binding on a set of aldose reductase inhibitors.
AID176748Dose required for inhibition of sorbital accumulation in the sciatic nerve of streptozotocin- induced diabetic rat.1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Novel, highly potent aldose reductase inhibitors: (R)-(-)-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) and its congeners.
AID34668In vitro inhibitory activity against aldose reductase in porcine lens.1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Novel, highly potent aldose reductase inhibitors: (R)-(-)-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) and its congeners.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (3.13)18.2507
2000's18 (56.25)29.6817
2010's10 (31.25)24.3611
2020's3 (9.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.35

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.35 (24.57)
Research Supply Index3.71 (2.92)
Research Growth Index5.88 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (21.21%)5.53%
Reviews7 (21.21%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (57.58%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]