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Oxybutynin

CAS# 5633-20-5

Oxybutynin

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Chemical structure

Oxybutynin

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Chemical Properties of Oxybutynin

Cas No. 5633-20-5 SDF Download SDF
PubChem ID 4634 Appearance Powder
Formula C22H31NO3 M.Wt 357.49
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 100 mg/mL (279.73 mM; Need ultrasonic)
H2O : ≥ 50 mg/mL (139.86 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 4-(diethylamino)but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
SMILES CCN(CC)CC#CCOC(=O)C(C1CCCCC1)(C2=CC=CC=C2)O
Standard InChIKey XIQVNETUBQGFHX-UHFFFAOYSA-N
Standard InChI InChI=1S/C22H31NO3/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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Oxybutynin

DescriptionOxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties. Target: mAChR Oxybutynin 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 competitively antagonizes the M1, M2, and M3 subtypes of the muscarinic acetylcholine receptor. It also has direct spasmolytic effects on bladder smooth muscle as a calcium antagonist and local anesthetic, but at concentrations far above those used clinically. Oxybutynin is available orally in generic formulation or as the brand-names Ditropan, Lyrinel XL, or Ditrospam, as a transdermal patch under the brand name Oxytrol, and as a topical gel under the brand name Gelnique. Oxybutynin is also a possible treatment of hyperhidrosis (hyper-active sweating) [1-3].

References:
[1]. Tupker, R.A., A.M. Harmsze, and V.H. Deneer, Oxybutynin therapy for generalized hyperhidrosis. Archives of dermatology, 2006. 142(8): p. 1065-1086. [2]. Mijnhout, G., et al., Oxybutynin: dry days for patients with hyperhidrosis. Neth J Med, 2006. 64(9): p. 326-8. [3]. Schollhammer, M. and L. Misery, Treatment of hyperhidrosis with oxybutynin. Archives of dermatology, 2007. 143(4): p. 543-551.

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Preparing Stock Solutions of Oxybutynin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7973 mL 13.9864 mL 27.9728 mL 55.9456 mL 69.932 mL
5 mM 0.5595 mL 2.7973 mL 5.5946 mL 11.1891 mL 13.9864 mL
10 mM 0.2797 mL 1.3986 mL 2.7973 mL 5.5946 mL 6.9932 mL
50 mM 0.0559 mL 0.2797 mL 0.5595 mL 1.1189 mL 1.3986 mL
100 mM 0.028 mL 0.1399 mL 0.2797 mL 0.5595 mL 0.6993 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Oxybutynin

Oxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties.

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References on Oxybutynin

Randomized, Placebo- and Active-Controlled Crossover Study of the Safety and Efficacy of THVD-102, a Fixed-dose Combination of Oxybutynin and Pilocarpine, in Subjects With Primary Focal Hyperhidrosis.[Pubmed:28300854]

J Drugs Dermatol. 2017 Feb 1;16(2):127-132.

BACKGROUND: While muscarinic antagonists (anticholinergics) have shown efficacy in treating primary focal hyperhidrosis (PFH), side effects - most commonly dry mouth - are intolerable for most patients. THVD-102, a fixed-dose combination product has been developed combining Oxybutynin, a muscarinic antagonist, and pilocarpine, a muscarinic agonist. The pilocarpine is at a dose level and release profile optimized to correct salivary flow impaired by Oxybutynin yet not interfere with the therapeutic muscarinic antagonist effect of Oxybutynin upon the sweat glands. OBJECTIVES: This study evaluated safety, efficacy, dry mouth and quality of life with THVD-102 (Oxybutynin 7.5 mg / pilocarpine 7.5 mg) in subjects with axillary and / or palmar PFH. METHODS: After a 21-day open label treatment period with Oxybutynin 5 mg twice daily to determine susceptibility of subjects to develop dry mouth, eligible subjects were randomized to 1 of 6 sequences of 3 study treatments (THVD-102, Oxybutynin 7.5 mg, and placebo) in sequential 21day double-blind crossover treatment periods, each preceded by a washout period of at least 7 days. RESULTS: A total of 24 subjects were randomized and 19 finished all crossover treatments. Changes from baseline to end of treatment in symptoms associated with PFH were statistically significant for both THVD-102 versus placebo and for Oxybutynin versus placebo as assessed by multiple measures. Beneficial trends, not statistically significant, for gravimetric measurements were also observed. There were no statistically significant differences between THVD-102 and Oxybutynin in PFH efficacy. Fewer subjects reported moderate to severe dry mouth while receiving THVD-102 compared to Oxybutynin and more subjects categorized their dry mouth as none or mild while receiving THVD-102 compared to Oxybutynin. Differences in reported dry mouth were statistically significant. CONCLUSION: THVD-102 was generally well-tolerated. Both THVD-102 and Oxybutynin 7.5 mg twice daily were effective in treating PFH. THVD-102 was associated with significantly reduced dry mouth compared to Oxybutynin. J Drugs Dermatol. 2017;16(2):127-132..

Histopathologic and Urodynamic Effects of the Anticholinergic Drugs Oxybutynin, Tolterodine, and Trospium on the Bladder.[Pubmed:28120444]

Low Urin Tract Symptoms. 2017 Jan;9(1):52-56.

OBJECTIVES: This study aimed to evaluate the effects of intravesical instillation of the anticholinergic drugs Oxybutynin, tolterodine, and trospium on bladder capacity and histopathological changes in the bladder mucosa. METHODS: The study included 20 male New Zealand white rabbits that were randomly allocated to four groups of five. In the Oxybutynin, tolterodine, and trospium groups, the drugs used were 1 mg/kg of crushed tablet mixed with 5 mL of saline, instilled intravesically once per day for 4 weeks. The control group was administered only 5 mL of saline once per day for 4 weeks. Urodynamic measurement of the bladder was made before and after treatment. At the end of the treatment the animals were killed and the bladders were evaluated histopathologically. RESULTS: There were no significant differences between pre- and post-treatment bladder capacity in any of the groups (P > 0.05). Histopathological evaluation showed that the mucosal epithelium was intact and there was minor inflammation in the control group and Oxybutynin group (P > 0.05), whereas there was destruction of the mucosal epithelium and findings of diffuse inflammation in the tolterodine (P = 0.014) and trospium (P = 0.014) groups. CONCLUSION: Intravesical Oxybutynin treatment was observed to be safe; however, a single daily dose of Oxybutynin may not be sufficient to increase bladder capacity. Intravesical use of trospium and tolterodine at high doses caused epithelial destruction and diffuse inflammation in the bladder mucosa. The irritation associated with epithelial destruction and inflammation prevented an increase in bladder capacity.

Methadone-Induced Hyperhidrosis Treated With Oxybutynin.[Pubmed:28244893]

J Addict Med. 2017 May/Jun;11(3):237-238.

OBJECTIVES: This case report aims to help healthcare providers and methadone clinic patients to recognize one of the less recognized adverse effects of methadone, hyperhidrosis, and to suggest Oxybutynin as a possible solution. METHODS: A 35-year-old man on methadone maintenance therapy presented with excessive sweating, which began promptly after methadone was introduced. Urine toxicology was conducted every 2 weeks to rule out other illicit substances that may have contributed to the sweating. RESULTS: Oxybutynin (5 mg PO QID) resulted in cessation of the methadone-induced hyperhidrosis within 2 days of starting the medication. CONCLUSIONS: Methadone-induced excessive sweating is an adverse effect of the medication that reportedly affects up to 45% of those prescribed methadone, and Oxybutynin is a potent treatment for methadone-induced excessive sweating.

Transcutaneous Electrical Nerve Stimulation Combined with Oxybutynin is Superior to Monotherapy in Children with Urge Incontinence: A Randomized, Placebo Controlled Study.[Pubmed:28327453]

J Urol. 2017 Aug;198(2):430-435.

PURPOSE: We evaluated whether combination therapy with transcutaneous electrical nerve stimulation and Oxybutynin results in a superior treatment response compared to either therapy alone in children with urge incontinence. MATERIALS AND METHODS: In this placebo controlled study 66 children with a mean +/- SD age of 7.3 +/- 1.6 years who were diagnosed with urge incontinence were randomized to 3 treatment groups. Group 1 consisted of 22 children undergoing transcutaneous electrical nerve stimulation plus active Oxybutynin administration. Group 2 included 21 children undergoing active transcutaneous electrical nerve stimulation plus placebo Oxybutynin administration. Group 3 consisted of 23 children undergoing active Oxybutynin administration plus placebo transcutaneous electrical nerve stimulation. The children received active or placebo transcutaneous electrical nerve stimulation over the sacral S2 to S3 outflow for 2 hours daily in combination with 5 mg active or placebo Oxybutynin twice daily. The intervention period was 10 weeks. Primary outcome was number of wet days weekly. Secondary outcomes were severity of incontinence, frequency, maximum voided volume over expected bladder capacity for age, average voided volume over expected bladder capacity for age and visual analogue scale score. RESULTS: Combination therapy was superior to Oxybutynin monotherapy, with an 83% greater chance of treatment response (p = 0.05). Combination therapy was also significantly more effective than transcutaneous electrical nerve stimulation monotherapy regarding reduced number of wet days weekly (mean difference -2.28, CI -4.06 to -0.49), severity of incontinence (-3.11, CI -5.98 to -0.23) and daily voiding frequency (-2.82, CI -4.48 to -1.17). CONCLUSIONS: Transcutaneous electrical nerve stimulation in combination with Oxybutynin for childhood urge incontinence was superior to monotherapy consisting of transcutaneous electrical nerve stimulation or Oxybutynin, although the latter only reached borderline statistical significance. Furthermore, transcutaneous electrical nerve stimulation was associated with a decreased risk of Oxybutynin induced post-void residual urine greater than 20 ml.

Description

Oxybutynin is an anticholinergic agent, which inhibits vascular Kv channels in a concentration-dependent manner, with an IC50 of 11.51 μM.

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