Diazoxide

Diazoxide is an ATP-sensitive potassium channel activator ; can be used to treat hyperinsulinism.

Solid

Diazoxide is a benzothiadiazine that is the S,S-dioxide of 2H-1,2,4-benzothiadiazine which is substituted at position 3 by a methyl group and at position 7 by chlorine. A peripheral vasodilator, it increases the concentration of glucose in the plasma and inhibits the secretion of insulin by the beta- cells of the pancreas. It is used orally in the management of intractable hypoglycaemia and intravenously in the management of hypertensive emergencies. It has a role as an antihypertensive agent, a sodium channel blocker, a vasodilator agent, a K-ATP channel agonist, a beta-adrenergic agonist, a cardiotonic drug, a bronchodilator agent, a sympathomimetic agent and a diuretic. It is a benzothiadiazine, a sulfone and an organochlorine compound.|A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.|Diazoxide is a benzothiadiazine derivate with antihypertensive and hyperglycemic activities. Diazoxide increases membrane permeability to potassium ions in vascular smooth muscle, thereby stabilizing the membrane action potential and preventing vascular smooth muscle contraction; this results in peripheral vasodilatation and decreases in peripheral vascular resistance. This agent also inhibits insulin release by interacting with ATP-sensitive potassium channels of pancreatic islet beta-cells.

Preparation of diazine crude.Take 5-chloro-2-aminobenzenesulfonamide (III) 100g, potassium carbonate 100g, chloroform 600g, Followed by 1L round bottom three-necked flask, Acetyl chloride 80g was added dropwise with stirring at 0 to 10 ° C, Add at room temperature for 6 hours. After the reaction is completed, The reaction solution was poured into 800g of ice water, Slow stirring, Standing, Divided chloroform layer, Concentrate to dryness under reduced pressure.To the resulting oil was added diphenyl ether 400g, The reaction was stirred at 250 ~ 250 for 1 hour, Cool to room temperature, Solid was isolated, washed with ethanol, dry, A pale yellow diazine crude was obtained.(C) Preparation of diazoxide (I).The resulting diazine crude product was recrystallized from 80percent ethanol, Product dry, Smash, Obtained white crystalline powder (sample 3), Diazoxide (I) 85.5 g.The total molar yield is 74.3percent as 5-chloro-2-nitrobenzenesulfonamide.

Diazoxide reduces status epilepticus neuron damage in diabetes.

Molecular Weight:230.67
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:229.9916763
Monoisotopic Mass:229.9916763
Topological Polar Surface Area:66.9
Heavy Atom Count:14
Complexity:360
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes