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82964-04-3

82964-04-3 Structure

82964-04-3 Structure
IdentificationBack Directory
[Name]

TOLRESTAT
[CAS]

82964-04-3
[Synonyms]

CS-148
Alredase
AY-27773
Lorestat
TOLRESTAT
Aldredase
Tolrestatin
TOLRESTAT USP/EP/BP
Tolrestat, AY 27773
TOLRESTAT(FORR&DONLY)
AY-27773;AY 27773; AY27773
TolrestattolrestattolrestatTolrestat
N-[[6-Methoxy-5-(trifluoromethyl)naphthalen-1-yl]thioxomethyl]-N-methylglycine
N-[[6-Methoxy-5-(triiquoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylglyeine
2-(6-Methoxy-N-Methyl-5-(trifluoroMethyl)naphthalene-1-carbothioaMido)acetic acid
Glycine, N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methyl-
[(6-Methoxy-5-trifluoromethyl-naphthalene-1-carbothioyl)-methyl-amino]-acetic acid
[Molecular Formula]

C16H14F3NO3S
[MDL Number]

MFCD00864170
[MOL File]

82964-04-3.mol
[Molecular Weight]

357.35
Chemical PropertiesBack Directory
[Melting point ]

164-165°
[Boiling point ]

498.1±55.0 °C(Predicted)
[density ]

1.399±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
[form ]

powder
[pka]

3.49±0.10(Predicted)
[color ]

white to beige
[CAS DataBase Reference]

82964-04-3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Phosphorus pentasulfide-->Glycine methyl ester hydrochloride-->Sarcosine-->1-Naphthoic acid-->1,5-Dimethylnaphthalene
Hazard InformationBack Directory
[Description]

Tolrestat is a long-acting aldose reductase inhibitor reportedly useful in the prophylaxis of diabetic neuropathy, retinopathy and cataracts.
[Chemical Properties]

Crystalline, melting point 164-165°C.
Tolrestat Methyl Ester: C17H16F3NO3S. Melting point 109-110°C.
[Originator]

American Home Products (USA)
[Uses]

Alredase (Wyeth-Ayerst).
[Definition]

ChEBI: Tolrestat is a member of naphthalenes. It has a role as an EC 1.1.1.21 (aldehyde reductase) inhibitor.
[Brand name]

Alredase
[Biochem/physiol Actions]

Tolrestat is considered to be effective in treating the consequences of diabetes including neuropathy, nephropathy, retinopathy and esophageal motility and vibration perception. Tolrestat is also believed to have lesser or no toxic effects.
[References]

[1] KAZIMIR SESTANJ. N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine (Tolrestat), a potent, orally active aldose reductase inhibitor[J]. Journal of Medicinal Chemistry, 1984, 27 3: 255-256. DOI: 10.1021/jm00369a003
[2] M L MCCALEB. Intervention with the aldose reductase inhibitor, tolrestat, in renal and retinal lesions of streptozotocin-diabetic rats.[J]. Diabetologia, 1991, 34 10: 695-701. DOI: 10.1007/bf00401513
[3] STEFANIA BANDITELLI . A New Approach Against Sugar Cataract Through Aldose Reductase Inhibitors[J]. Experimental eye research, 1999, 69 5: Pages 533-538. DOI: 10.1006/exer.1999.0729
Spectrum DetailBack Directory
[Spectrum Detail]

TOLRESTAT(82964-04-3)1HNMR
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