1508-65-2 Usage
Description
Oxybutynin hydrochloride is a white to off-white solid that belongs to the class of anticholinergic medications. It is an inhibitor of proliferation and suppresses gene expression in bladder smooth muscle cells. Additionally, it acts as an antagonist of M1, M2, and M3 muscarinic acetylcholine receptors, making it a versatile pharmaceutical compound.
Uses
Used in Pharmaceutical Industry:
Oxybutynin hydrochloride is used as an anticholinergic agent for treating overactive bladder and urinary incontinence. Its action as an antagonist of muscarinic receptors helps to reduce involuntary muscle contractions in the bladder, providing relief from symptoms such as frequent urination and urgency.
Used in Bladder Smooth Muscle Cell Research:
Oxybutynin hydrochloride is used as a research tool for studying the effects of anticholinergic agents on bladder smooth muscle cells. Its ability to inhibit proliferation and suppress gene expression in these cells makes it a valuable compound for understanding the underlying mechanisms of bladder dysfunction and developing new therapeutic strategies.
Used in Antagonist Research:
Oxybutynin hydrochloride is used as an antagonist of M1, M2, and M3 muscarinic acetylcholine receptors in the field of receptor pharmacology. This application helps researchers investigate the role of these receptors in various physiological processes and develop targeted therapies for conditions related to muscarinic receptor dysregulation.
Brand Name:
Oxybutynin hydrochloride is commercially available under the brand name Ditropan (ALZA), which is widely used for the treatment of overactive bladder and urinary incontinence.
Originator
Ditropan, Marion , US ,1975
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.
Therapeutic Function
Spasmolytic
Biological Activity
oxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties.
Biochem/physiol Actions
Muscarinic acetylcholine receptor antagonist; inhibits proliferation of bladder smooth muscle cells, perhaps by downregulation of growth promoting genes.
Clinical Use
Urinary frequency, urgency and incontinence
Neurogenic bladder instability and nocturnal
enuresis
Safety Profile
Poison by ingestion, intravenous, and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. An eye irritant. Human systemic effects: coma, mydriasis, rate changes. An anticholinergic agent. When heated to decomposition it e
Drug interactions
Potentially hazardous interactions with other drugs
Anti-arrhythmics: increased risk of antimuscarinic
side effects with disopyramide.
Other antimuscarinic agents: increased
antimuscarinic effects.
Metabolism
Oxybutynin undergoes extensive first-pass metabolism,
particularly by the cytochrome P450 isoenzyme
CYP3A4. One of the metabolites, N-desethyloxybutynin
is pharmacologically active.
Oxybutynin and its metabolites are excreted in the urine
and faeces.
Check Digit Verification of cas no
The CAS Registry Mumber 1508-65-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,0 and 8 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1508-65:
(6*1)+(5*5)+(4*0)+(3*8)+(2*6)+(1*5)=72
72 % 10 = 2
So 1508-65-2 is a valid CAS Registry Number.
InChI:InChI=1/C22H31NO3.ClH/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20;/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3;1H
1508-65-2Relevant articles and documents
POLYMORPHIC FORMS OF (R)-OXYBUTYNIN HYDROCHLORIDE
-
Paragraph 0152-0154, (2021/11/13)
Polymorphic forms of (R)-oxybutynin HC1, including three crystalline forms, are prepared and characterized. Uses of the various polymorphic forms of (R)-oxybutynin HC1 for Obstructive Sleep Apnea (OS A) treatment are also disclosed.
CRYSTALLINE OXYBUTYNIN AND PROCESS FOR PREPARING THE SAME
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Page/Page column 6, (2009/10/30)
The present invention relates to a crystalline oxybutynin base and process for preparing the same. Further, this invention discloses a process for preparing an acid addition salt of oxybutynin employing the crystalline oxybutynin base.
QUATERNARY AMMONIUM COMPOUNDS
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Page 8, (2008/06/13)
The invention features quaternary ammonium compounds of formula I, described herein, and their use in treating asthma, chronic obstructive pulmonary disorder, allergic rhinitis, and infectious rhinitis.
