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Tolrestat

Tolrestat structure

CAS No:
82964-04-3
Formula:
C16H14F3NO3S
Chemical Name:
Tolrestat
Synonyms:
Glycine,N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methyl-;N-[[6-Methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine;Tolrestat;AY 27773;Tolrestatin;Alredase;Lorestat;2-(6-Methoxy-N-methyl-5-(trifluoromethyl)naphthalene-1-carbothioamido)aceticacid
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System

Description

Tolrestat is a potent, orally active aldose reductase inhibitor with IC50 of 35 nM.

Tolrestat is a member of naphthalenes. It has a role as an EC 1.1.1.21 (aldehyde reductase) inhibitor.|Tolrestat (INN) (AY-27773) is an aldose reductase inhibitor which was approved for the control of certain diabetic complications. While it was approved for marketed in several countries, it failed a Phase III trial in the U.S. due to toxicity and never received FDA approval. It was sold under the tradename Alredase but was discontinued by Wyeth in 1997 because of the risk of severe liver toxicity and death.

Tolrestat Basic Attributes

Molecular Weight：

357.35

Exact Mass：

357.35

UNII：

0T93LG5NMK

ATC Code：

A - Alimentary tract and metabolism

Characteristics

PSA：

81.9

XLogP3：

3.41

Density：

1.4±0.1 g/cm3

Melting Point：

164-165 °C

Boiling Point：

498.1±55.0 °C at 760 mmHg

Flash Point：

255.0±31.5 °C

Refractive Index：

1.602

Toxicity

Toxicity Summary：

Oral, mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50 = 980 mg/kg.

Drug Information

Drug Indication：

For the pharmacological control of certain diabetic complications.

MeSH：

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

MeSH Entry Terms：

AY 27773

Tolrestat Use and Manufacturing

Aldose reductase inhibitor with low toxicity. It is used to treat and prevent diabetic complications, such as diabetic neuropathy, kidney disease, cataracts, retinopathy, etc.

Computed Properties

Molecular Weight:357.3
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:357.06464897
Monoisotopic Mass:357.06464897
Topological Polar Surface Area:81.9
Heavy Atom Count:24
Complexity:486
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes