Tolrestat

HCID 53359
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
82964-04-3
Standard SMILES
COc1ccc2c(C(=S)N(C)CC(=O)O)cccc2c1C(F)(F)F
InChIKey
LUBHDINQXIHVLS-UHFFFAOYSA-N
Molecular formula
C16H14F3NO3S
Average molar mass
357.3 g/mol
Monoisotopic mass
357.06464897

Overview

Tolrestat is a member of naphthalenes. It has a role as an EC 1.1.1.21 (aldehyde reductase) inhibitor.

Names & identifiers

Preferred name
Tolrestat
IUPAC
2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetic acid
English name
TOLRESTAT
Molecular formula
C16H14F3NO3S
Molecular weight
357.35

Names & synonyms

TOLRESTAT82964-04-3AlredaseAY-27773TolrestatumAY-27,7730T93LG5NMK2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetic acidN-(6-Methoxythio-5-(trifluoromethyl)-1-naphthoyl)sarcosineCHEBI:48549DTXSID80904890N-{[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]carbonothioyl}-N-methylglycine
Show more names
CS-148LorestatAldredaseTolrestatinTolrestat, AY 27773TOLRESTAT USP/EP/BPTOLRESTAT(FORR&DONLY)
Glycine, N-((6-methoxy-5-(trifluoromethyl)-1-naphthalenyl)thioxomethyl)-N-methyl-N-((5-(trifluoromethyl)-6-methoxy-1-naphthalenyl)thioxomethyl)-N-methylglycineN-[6-Methoxythio-5-(trifluoromethyl)-1-naphthoyl]sarcosineAlderase2-((6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl)-methylamino)acetic acidGlycine, N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methyl-N-((6-methoxy-5-(trifluoromethyl)naphthalen-1-yl)carbonothioyl)-N-methylglycineN-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine

Database identifiers

CAS
82964-04-3
PubChem CID
53359
DTXSID
DTXSID80904890
ChEMBL
CHEMBL436
ChEBI
CHEBI:48549
UNII
0T93LG5NMK
Nikkaji
J23.281E

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
81.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
4
Heavy atoms
24

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Alimentary tract and metabolism -> Drugs used in diabetes

Physicochemical properties

Melting point
164 · 164-165°
Boiling point
498.1 · 498.1±55.0 °C(Predicted)
Density
1.399 · 1.399±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
form
powder

Safety & regulation

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Tolrestat

vMost-DILI-concern

8

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
WGK 3
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H332-H335
Precautionary statements
P261-P280-P305+P351+P338

Chemistry & industry

Pharmacology

ATC Code · 2 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications · 4 items

DescriptionTolrestat is a long-acting aldose reductase inhibitor reportedly useful in the prophylaxis of diabetic neuropathy, retinopathy and cataracts.

DescriptionTolrestat is an aldose reductase inhibitor (IC50 = 35 nM for the bovine lens enzyme). Dietary administration of tolrestat decreases sciatic nerve galactitol accumulation in a rat model of galactosemia (ED50 = 7.3 mg/kg per day) and sciatic nerve sorbitol accumulation (ED50 = 4.8 mg/kg per day) in a rat model of diabetes induced by streptozotocin (STZ; ). It also decreases urinary total protein exretion in a rat model of STZ-induced diabetes when administered at a dose of 25 mg/kg per day. Topical administration of tolrestat (2 and 3% in 10 μl four times per day) decreases levels of galactitol in the lens of and inhibits cataract formation in rats fed a high-galactose diet.

UsesTolrestat is an aldose reductase inhibitor.

UsesAlredase (Wyeth-Ayerst).

Upstream & downstream products

Suppliers61 total

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Aladdin Scientific[email protected]

Additional notes

DefinitionChEBI: Tolrestat is a member of naphthalenes. It has a role as an EC 1.1.1.21 (aldehyde reductase) inhibitor.

Related reactions

2 records
New reaction record

Compound notes

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