Zenarestat

HCID 5724

Grundinformationen

CAS
112733-06-9
Standard-SMILES
O=C(O)Cn1c(=O)n(Cc2ccc(Br)cc2F)c(=O)c2ccc(Cl)cc21
InChIKey
SXONDGSPUVNZLO-UHFFFAOYSA-N
Summenformel
C17H11BrClFN2O4
Durchschnittliche Molmasse
441,6 g/mol
Monoisotopische Masse
439,95747483

Namen und Bezeichner

Bevorzugter Name
Zenarestat
IUPAC
2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetic acid
Englischer Name
Zenarestat
Summenformel
C17H11BrClFN2O4
Molmasse
441.639

Namen und Synonyme

Zenarestat112733-06-9FR-74366FK-366ZenarestatumFR 74366Fk366CI-1014DTXSID0047296FR74366180C9PJ8JT2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetic acid
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
112733-06-9
PubChem CID
5724
DTXSID
DTXSID0047296
ChEMBL
CHEMBL10413
UNII
180C9PJ8JT
Nikkaji
J248.078F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,3
Polarare Oberfläche (TPSA)
77,9 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
26

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt
223 · 223-224°
Siedepunkt
624.4 · 624.4±65.0 °C(Predicted)
Dichte
1.737 · 1.737
Löslichkeit
100 mg/mL · DMSO : 100 mg/mL (226.43 mM; Need ultrasonic)
pka
3.76 · 3.76±0.10(Predicted)
Aggregatzustand
Solid

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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.

Anwendungen

VerwendenTreatment of diabetic neuropathy (aldose reductase inhibitor).

Anbieter7 Anbieter

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]

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