Zenarestat

HCID 5724

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

Zenarestat112733-06-9FR-74366FK-366ZenarestatumFR 74366Fk366CI-1014DTXSID0047296FR74366180C9PJ8JT2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetic acid
Show more names
CI10143-(2-Fluoro-4-bromobenzyl)-7-chloro-2,4(1H,3H)-dioxoquinazoline-1-acetic acid[3-(4-Bromo-2-fluorobenzyl)-7-chloro-2,4-dioxo-3,4-dihydro-1(2H)- quinazolinyl]acetic acid3-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-3,4-dihydro-2,4-dioxo-1(2H)-quinazolineacetic acid1(2H)-Quinazolineacetic acid, 3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-3,4-dihydro-2,4-dioxo-
DTXCID80272962-(3-((4-bromo-2-fluorophenyl)methyl)-7-chloro-2,4-dioxoquinazolin-1-yl)acetic acidRefChem:904824[3-(4-bromo-2-fluorobenzyl)-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2h)-yl]acetic acidCHEMBL104132-(3-(4-bromo-2-fluorobenzyl)-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetic acid1(2H)-Quinazolineaceticacid, 3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-3,4-dihydro-2,4-dioxo-3-(4-Bromo-2-fluorobenzyl)-7-chloro-3,4-dihydro-2,4-dioxo-1(2H)-quinazolineacetic acid

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

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section188.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0047296]

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

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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.

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

UsesTreatment of diabetic neuropathy (aldose reductase inhibitor).

Suppliers7 total

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
晶墨(厦门)生物科技有限公司13621943973; 13621943973 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
重庆卡兰医药有限公司[email protected]

Related reactions

3 records

Compound notes

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