Gliquidone
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Gliquidone
structure -
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CAS No:
33342-05-1
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Formula:
C27H33N3O6S
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Chemical Name:
Gliquidone
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Synonyms:
Benzenesulfonamide,N-[(cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]-;N-[(Cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide;Gliquidone;AR-DF 26;Glurenorm;ARDF 26SE;Beglynor;TangShiPing;TangShenPing;1-Cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea;1-Cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl]urea;ZINC 01482077;ZINC 1482077;2411524-48-4
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Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System
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CAS No:
Description
Gliquidone (AR-DF 26) is an anti-diabetic drug in the sulfonylurea class, used in the treatment of diabetes mellitus type 2.
Solid
1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea is a member of isoquinolines.|Gliquidone is a sulfonylurea drug used to treat diabetes mellitus type 2. It is an ATP-dependent K+ (KATP) channel blocker. This block causes a depolarization which leads to activation of voltage-dependent Ca channels and Ca2+ influx, and eventually increases insulin release.|Gliquidone is a potent, second-generation sulfonylurea with antihyperglycemic activity. Like other second-generation compounds, gliquidone exerts greater binding affinity to SUR1 and increased potency compared to first-generation compounds. In addition, this agent exerts peroxisome proliferator-activated receptor (PPAR) gamma agonistic activity.
Gliquidone Basic Attributes
527.63
527.63
251-463-2
C7C2QDD75P
DTXSID4023096
C72798
A10BB08|A - Alimentary tract and metabolism
29147000
Drug Information
Used in the treatment of diabetes mellitus type 2.
Gliquidone is an anti-diabetic drug in the sulfonylurea class. In patients with diabetes mellitus, there is a deficiency or absence of a hormone manufactured by the pancreas called insulin. Insulin is the main hormone responsible for the control of sugar in the blood. Gliquidone is an antidiabetic medication which is used in those patients with adult maturity onset or non-insulin dependent diabetes (NIDDM). It works by lowering blood sugar levels by stimulating the production and release of insulin from the pancreas. It also promotes the movement of sugar from the blood into the cells in the body which need it.
Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)
The mean terminal half-life was approximately 8 hours (range 5.7-9.4 hours)
The mechanism of action of gliquidone in lowering blood glucose appears to be dependent on stimulating the release of insulin from functioning pancreatic beta cells, and increasing sensitivity of peripheral tissues to insulin. Gliquidone likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin.
AR-DF 26
Gliquidone Use and Manufacturing
Isoquinoline (30 g, 74.6 mmol), solvent 2, 5-dimethyltetrahydrofuran (300 mL) and anhydrous potassium carbonate (21 g, 151.9 mmol) were sequentially added to a 500 mL reaction flask. Open the stirring and heating, incubated at 40 °C for 30 minutes, and then slowly added cyclohexyl isocyanate (11.2g, 89.5mmol), the control was added dropwise over about 30 minutes after completion of the dropping temperature was raised, 90 °C Heated to reflux for 4 hours. The solvent 2, 5_ dimethyltetrahydrofuran was recovered under reduced pressure to give a white solid. To the reaction flask was added 200mL water, hydrochloric acid was slowly added dropwise to adjust PH = 3, cooled to 0-5 °C and stirred for 1 hour, filtered to give crude gliquidone, a yield of 98percent. The resulting gliquidone crude product into 5L of the three-necked flask to the bottle was added 3L of methanol, heated to 40 °C, the system was added ammonia / methanol, adjust the pH to 3, the gliquidone Crude product completely dissolved, and then continue to add 3g of neutral alumina and 3g silica gel (200-300 mesh), the use of alumina with silica gel completely adsorbed impurities in the system. 40 °C under stirring for 2 hours, filtered, the filtrate was adjusted with 3 M hydrochloric acid PH = 3, lower the temperature, 0-5 °C under agitation crystallization 4 hours. Filter, filter cake were washed with water, ethanol. 40 °C under vacuum for 12 hours to give a white granular solid, that is, gliquidone. Purity 99.75percent, yield 80percent.
Antidiabetic
Computed Properties
Molecular Weight:527.6
XLogP3:4.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:527.20900695
Monoisotopic Mass:527.20900695
Topological Polar Surface Area:130
Heavy Atom Count:37
Complexity:948
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract from the above information
Registered Holders
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Boehringer Ingelheim Shanghai Pharmaceuticals Co., Ltd.
Active
China
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Boehringer Ingelheim (China) Investment Co., Ltd.
Active
China
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Tianke (Jingzhou) Pharmaceutical Co., Ltd.
Active
China
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