oxyphencyclimine

Originator

Vio-Thene ,Rowell,US,1959

The Uses of oxyphencyclimine

Antulcus can be used as a potential inhibitor for insulin fibril formation.

Background

Oxyphencyclimine is an anticholinergic drug (trade name Daricon) used in treating peptic ulcers.

Indications

For the treatment of peptic ulcer disease and the relief of smooth muscle spasms in gastrointestinal disorders.

Definition

ChEBI: Oxyphencyclimine is a monocarboxylic acid.

Manufacturing Process

To a stirred solution of 8.8 grams (0.1 mol) of 1,3-diaminobutane in 150 ml of ethanol maintained at 0° to 5°C, there was added 25.8 grams (0.1 mol) of ethyl chlorimidoacetate hydrochloride during a period of 20 minutes. After the mixture had been stirred at 0° to 5°C for two hours, it was acidified at this temperature by the addition of ethanolic hydrogen chloride. The mixture was warmed to room temperature and filtered to remove 4.3 grams of solid ammonium chloride. The filtrate was concentrated to approximately 40 ml, filtered and refrigerated. The solid which separated was isolated, washed with acetone and dried. There was obtained 7.4 grams (40% of the theoretical yield) of 2-chloromethyl-4-methyl-1,4,5,6-tetrahydropyrimidine hydrochloride melting at 158° to 160°C.
In a second step, cyclohexyl bromide was reacted with magnesium, then with benzoyl formic acid to give cyclohexylphenyl glycolic acid. A solution of 1.8 grams (0.01 mol) of 2-chloromethyl-1-methyl-1,4,5,6-tetrahydropyrimidine hydrochloride in 5 ml of water was made alkaline with 5 ml of 50% NaOH and extracted with ether. The ether solution, which contained the basic chloride, was dried over calcium sulfate and added to a solution of 2.3 grams (0.01 mol) of α-cyclohexylphenylglycolic acid in 75 ml of isopropanol. The solution was distilled to remove the ether, and 0.1 gram of powdered potassium iodide added to the residual isopropanol solution which was then refluxed for 6 hours. The solid which had separated was redissolved by the addition of 20 ml of ethanol and the solution charcoaled, concentrated, and cooled. The solid which separated, 1-methyl-1,4,5,6-tetrahydro-2-pyrimidylmethyl αcyclohexylphenyl-glycolate hydrochloride, weighed 1.4 grams and melted at 228° to 229°C with decomposition after recrystallization from ethanol.

brand name

Daricon (Pfizer).

Therapeutic Function

Spasmolytic

Pharmacokinetics

Oxyphencyclimine is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract. Oxyphencyclimine is an antimuscarinic, anticholinergic drug.

Metabolism

Not Available