Originator
Ditropan, Marion , US ,1975
Uses
Oxybutynin can be used as a pharmaceutical formulation for inhibitin body malodour.
Uses
Oxybutynin(Ditropan) is an anticholinergic medication used to relieve urinary and bladder difficulties, including frequent urination and inability to control urination (urge incontinence), by decreasing muscle spasms of the bladder.Oxybutynin contains one
Definition
ChEBI: Oxybutynin is a racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder. It has a role as a muscarinic antagonist, a muscle relaxant, an antispasmodic drug, a parasympatholytic, a calcium channel blocker and a local anaesthetic. It is a tertiary amino compound and a racemate. It contains an esoxybutynin and a (R)-oxybutynin.
Manufacturing Process
A mixture of 394.2 grams of methyl phenylcyclohexylglycolate and 293.1 grams of 4-diethylamino-2-butynyl acetate was dissolved with warming in 2.6 liters of n-heptane. The solution was heated with stirring to a temperature of 60° to 70°C and 8.0 grams of sodium methoxide were added. The temperature of the mixture was then raised until the solvent began to distill. Distillation was continued at a gradual rate and aliquots of the distillate were successively collected and analyzed for the presence of methyl acetate by measurement of the refractive index. The reaction was completed when methyl acetate no longer distilled, and the refractive index observed was that of pure heptane (nD26 = 1.3855). About 3? hours were required for the reaction to be completed.
The reaction mixture was then allowed to cool to room temperature, washed with water, and extracted with four 165 ml portions of 2 N hydrochloric acid. The aqueous extracts were combined and stirred at room temperature to permit crystallization of the hydrochloride salt of the desired product. Crystallization was completed by cooling the slurry in an ice bath, and the product was collected by filtration, pressed dry, and recrystallized from 750 ml of water. Yield of pure crystalline material, 323 grams.
Brand name
Oxytrol (Watson).
Therapeutic Function
Spasmolytic
General Description
Oxybutynin, 4-Diethylaminobut- 2-ynyl2-cyclohexyl-2- hydroxy-2-phenyl-ethanoate, (Oxytrol) wasone of the first agents specifically developed to exploit the effectsthat cholinergic blocking agents have on the bladder. Bycompetitively blocking the muscarinic receptors, it has directspasmolytic effects on bladder smooth muscle. This reductionin smooth muscle tone allows for greater volumes of urine tobe stored in the bladder, which results in less urinary incontinence,urgency, and frequency. Oxybutynin acts as a competitiveantagonist on M1, M2, and M3 receptor subtypes.
Synthesis
Oxybutynin, 4-diethylamino-2-butynylic ester |á-phenylclohexaneglycolic
acid (14.1.35), is synthesized either by a Mannich reaction using propargyl ester of
|á-phenyl-|á-cyclohexaneglycolic acid, paraform and diethylamine, or transesterification of
the methyl ester of |á-phenyl-|á-cyclohexaneglycolic acid using 1-acetoxy-4-diethylamino-
2-butene in the presence of sodium methoxide [26].
Veterinary Drugs and Treatments
Oxybutynin may be useful for the adjunctive therapy of detrusor
hyperreflexi
