Basic information
- CAS
112733-06-9- Standard SMILES
O=C(O)Cn1c(=O)n(Cc2ccc(Br)cc2F)c(=O)c2ccc(Cl)cc21- InChIKey
SXONDGSPUVNZLO-UHFFFAOYSA-N- Molecular formula
- C17H11BrClFN2O4
- Average molar mass
- 441.6 g/mol
- Monoisotopic mass
- 439.95747483
Names & identifiers
- Preferred name
- Zenarestat
- IUPAC
- 2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetic acid
- English name
- Zenarestat
- Molecular formula
- C17H11BrClFN2O4
- Molecular weight
- 441.639
Names & synonyms
Show more names
Database identifiers
- CAS
112733-06-9- PubChem CID
- 5724
- DTXSID
DTXSID0047296- ChEMBL
CHEMBL10413- UNII
- 180C9PJ8JT
- Nikkaji
- J248.078F
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 77.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 595
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 223 · 223-224°
- Boiling point
- 624.4 · 624.4±65.0 °C(Predicted)
- Density
- 1.737 · 1.737
- solubility
- 100 mg/mL · DMSO : 100 mg/mL (226.43 mM; Need ultrasonic)
- pka
- 3.76 · 3.76±0.10(Predicted)
- form
- Solid
- color
- White to off-white
- FDA UNII
- 180 C9PJ8JT · 180C9PJ8JT
Chemistry & industry
Pharmacology
Mechanism of Action
Polyneuropathy, damage of peripheral neurons, is common in diabetes mellitus patients and causes pain, sensory and motor deficits in the limbs. Zenarestat is an aldose reductase inhibitor which inhibits the metabolism of glucose by the polyol pathway, which possibly slows or reduces progression of polyneuropathy. Chronic hyperglycemia affects peripheral nerves by an extracellular mechanism with many types of glycation reactions and chemical rearrangements, and an intracellular route involving increased amounts of glucose passing through the polyol pathway. The polyol pathway allows cells to produce fructose from glucose, and has two steps, which require energy and enzymes. Aldose reductase catalyzes the conversion of glucose to sorbitol in the first step, while the second involves the oxidation of nicotinamide adenine dicnucleotide phosphate (conversion of NADPH to NADP). Chronic hyperglycemia causes damage by overactivity of the polyol pathway, causing a decrease in cellular NADPH levels, reducing the amount of glutathione (a free radical scavenger), and nitric oxide (a vasodilator), as well as increasing cellular sorbital levels, causing decreased levels of myo-inositol (necessary for Na-K ATPase function) and increased fructose, thus increasing AGE (advanced glycosylation end products), the byproduct of the polyol pathway. The suppression of the first step in the polyol pathway by zenarestat prevents these deleterious processes from occuring.
Applications
UsesTreatment of diabetic neuropathy (aldose reductase inhibitor).
Upstream & downstream products
Upstream raw materials
Suppliers7 total
Related reactions
Compound notes
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