Doxazosin

CAS# 74191-85-8

Doxazosin

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Chemical structure

Doxazosin

3D structure

Chemical Properties of Doxazosin

Cas No. 74191-85-8 SDF Download SDF
PubChem ID 3157 Appearance Powder
Formula C23H25N5O5 M.Wt 451.48
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in DMSO
Chemical Name [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone
SMILES COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4)N)OC
Standard InChIKey RUZYUOTYCVRMRZ-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
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.

Doxazosin Dilution Calculator

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Preparing Stock Solutions of Doxazosin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2149 mL 11.0747 mL 22.1494 mL 44.2988 mL 55.3734 mL
5 mM 0.443 mL 2.2149 mL 4.4299 mL 8.8598 mL 11.0747 mL
10 mM 0.2215 mL 1.1075 mL 2.2149 mL 4.4299 mL 5.5373 mL
50 mM 0.0443 mL 0.2215 mL 0.443 mL 0.886 mL 1.1075 mL
100 mM 0.0221 mL 0.1107 mL 0.2215 mL 0.443 mL 0.5537 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 Doxazosin

Doxazosin(UK 33274) is a quinazoline-derivative that selectively antagonizes postsynaptic α1-adrenergic receptors.

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References on Doxazosin

Antiangiogenic Effects of Doxazosin on Experimental Choroidal Neovascularization in Mice.[Pubmed:27992238]

J Ocul Pharmacol Ther. 2017 Jan/Feb;33(1):50-56.

PURPOSE: The present study was designed to evaluate the effects of Doxazosin on experimental choroidal neovascularization (CNV) in mice. METHODS: Six- to 8-week-old male C57BL/6 mice were divided into a control group and a Doxazosin-treated group (5 mg/kg, i.p., daily). Experimental CNV was induced by laser photocoagulation. Seven and 14 days after laser induction, fluorescein angiography, choroidal flat mounts, and histological studies were performed to evaluate the fluorescence leakage, area, and thickness of CNV lesions, respectively. In addition, western blot analysis was carried out to assess the inhibitory effects of Doxazosin on the PI3K/Akt/mTOR signaling pathway and the expression levels of hypoxia-inducible factor 1alpha (HIF-1alpha) and vascular endothelial growth factor (VEGF), which are involved in CNV model. RESULTS: Compared with the control group, the Doxazosin-treated group demonstrated significantly less fluorescence leakage on day 7 and 14 after laser induction. Both the area and the thickness of CNV lesions in the Doxazosin-treated group were significantly decreased. Mechanistically, PI3K/Akt/mTOR signaling pathway activation was significantly suppressed in the Doxazosin-treated group. The expression of HIF-1alpha and VEGF was also notably reduced by systemic Doxazosin treatment. CONCLUSIONS: Doxazosin exerts antiangiogenic actions in an experimental mouse model of CNV and may be a potential adjunctive therapy for neovascular age-related macular degeneration in humans.

Doxazosin Stimulates Galectin-3 Expression and Collagen Synthesis in HL-1 Cardiomyocytes Independent of Protein Kinase C Pathway.[Pubmed:28066244]

Front Pharmacol. 2016 Dec 20;7:495.

Doxazosin, a drug commonly prescribed for hypertension and prostate disease, increases heart failure risk. However, the underlying mechanism remains unclear. Galectin-3 is an important mediator that plays a pathogenic role in cardiac hypertrophy and heart failure. In the present study, we investigated whether Doxazosin could stimulate galectin-3 expression and collagen synthesis in cultured HL-1 cardiomyocytes. We found that Doxazosin dose-dependently induced galectin-3 protein expression, with a statistically significant increase in expression with a dose as low as 0.01 muM. Doxazosin upregulated collagen I and alpha-smooth muscle actin (alpha-SMA) protein levels and also induced apoptotic protein caspase-3 in HL-1 cardiomyocytes. Although we previously reported that activation of protein kinase C (PKC) stimulates galectin-3 expression, blocking the PKC pathway with the PKC inhibitor chelerythrine did not prevent Doxazosin-induced galectin-3 and collagen expression. Consistently, Doxazosin treatment did not alter total and phosphorylated PKC. These results suggest that Doxazosin-stimulated galectin-3 is independent of PKC pathway. To determine if the alpha1-adrenergic pathway is involved, we pretreated the cells with the irreversible alpha-adrenergic receptor blocker phenoxybenzamine and found that Doxazosin-stimulated galectin-3 and collagen expression was similar to controls, suggesting that Doxazosin acts independently of alpha1-adrenergic receptor blockade. Collectively, we show a novel effect of Doxazosin on cardiomycytes by stimulating heart fibrosis factor galectin-3 expression. The mechanism of action of Doxazosin is not mediated through either activation of the PKC pathway or antagonism of alpha1-adrenergic receptors.

Ultrasound image features of intravesical prostatic protrusion indicated failure of medication therapy of finasteride and doxazosin in patients with benign prostatic hyperplasia (LUTS/BPH).[Pubmed:27987130]

Int Urol Nephrol. 2017 Mar;49(3):399-404.

BACKGROUND: Intravesical prostatic protrusion (IPP) is a type of benign prostatic hyperplasia (BPH) adenoma, and it plays a critical role in the pathogenesis of bladder outlet obstruction in patients with lower urinary tract syndromes (LUTS/BPH). AIMS: The goal of this study was to investigate the effect of a combination therapy with finasteride and Doxazosin on IPP in BPU/LUTS patients. METHODS: A total of 322 BPH patients with enlarged prostatic volume as well as moderate to severe symptom scores were enrolled and divided into four groups according to the degree of IPP (IPP > 10 mm, 5-10 mm, <5 mm and no IPP) in this study. Aggravated International Prostatic Symptom Score (IPSS), acute urinary retention or relevant urinary complications were considered as failure of the therapy. The degrees of IPP were recorded before and after 6 months of treatment. Student's t test and chi (2) were performed between the baseline and endpoint of the therapy. RESULTS: The results showed that the total prostate volume (TPV) and transition zone volume (TZV) of the prostate decreased significantly after 6-month combination therapy (P < 0.05), while no significant changes in IPP were observed at that point (P > 0.05). Failure rates of the medication differed significantly among the four groups. CONCLUSIONS: The study indicated that the combination therapy using finasteride and Doxazosin could not reduce the degree of IPP. LUTS/BPH patients with IPP which contributes to the failure of medication tend to have a higher risk of progression.

Clinical study of duloxetine hydrochloride combined with doxazosin for the treatment of pain disorder in chronic prostatitis/chronic pelvic pain syndrome: An observational study.[Pubmed:28272220]

Medicine (Baltimore). 2017 Mar;96(10):e6243.

To explore the safety and efficacy of the selective 5-serotonin and norepinephrine reuptake inhibitor duloxetine hydrochloride and alpha-adrenergic receptor blocker (alpha-blocker) Doxazosin mesylate-controlled tablets in the treatment of pain disorder in chronic prostatitis/chronic pelvic pain syndrome (CP/CPPS).In all, 150 patients were enrolled and 126 patients completed the study (41 patients in the Doxazosin group, 41 patients in the sertraline group, and 44 patients in the duloxetine group). This was an open randomized 6-month study. CP/CPPS patients who met the diagnostic criteria were randomized into 3 groups. The patients in the duloxetine group received Doxazosin 4 mg + duloxetine 30 mg once a day, and the dosage of duloxetine was increased to 60 mg after a week. The patients in the Doxazosin group received Doxazosin 4 mg once a day. The patients in the sertraline group received Doxazosin 4 mg + sertraline 50 mg once a day. National Institutes of Health Chronic Prostatitis Symptom Index (NIH-CPSI) score, the short-form McGill Pain questionnaire (SF-MPQ), and the hospital anxiety and depression scale (HAD) were applied for evaluations during follow-up of 1, 3, and 6 months after treatment.There were slight positive significant correlations between NIH-CPSI scores and HAD scores, moderate positive significant correlations between the quality of life (QOL) and SF-MPQ, and slight positive significant correlations between HAD and QOL. The effective rate in the Doxazosin group was 4.88%, 19.51%, and 56.10% after 1, 3, and 6 months, respectively (P < 0.05). The SF-MPQ score in the Doxazosin group decreased to 1.80 +/- 1.29, 2.66 +/- 1.57, and 3.24 +/- 1.67 after 1, 3, and 6 months, respectively (P < 0.05). The HAD score in the Doxazosin group decreased to 2.24 +/- 2.17, 4 +/- 2.11, and 4.90 +/- 2.62 after 1, 3, and 6 months, respectively (P < 0.05). The effective rate in the sertraline group was 9.76%, 36.59%, and 63.41% after 1, 3, and 6 months, respectively. The SF-MPQ score in the sertraline group decreased to 1.76 +/- 1.28, 3.07 +/- 2, and 3.93 +/- 2.53 after 1, 3, and 6 months, respectively (P < 0.05). The HAD score in the sertraline group decreased to 3.56 +/- 4.11, 5.73 +/- 5.26, and 7.27 +/- 6.50 after 1, 3, and 6 months, respectively (P < 0.05). The effective rate in the duloxetine group was 36.36%, 88.64%, and 88.64% after 1, 3, and 6 months, respectively. The SF-MPQ score in the duloxetine group decreased to 3.61 +/- 2.54, 6.05 +/- 3.66, and 7.41 +/- 4.26 after 1, 3, and 6 months, respectively (P < 0.05). The HAD score in the duloxetine group decreased to 3.14 +/- 3.28, 6.93 +/- 3.90, and 9.43 +/- 4.67 after 1, 3, and 6 months, respectively (P < 0.05). There were significant differences in the reduction of the NIH-CPSI score and the SF-MPQ score between the duloxetine group and the sertraline group and between the duloxetine group and the Doxazosin group (P < 0.01). There were significant differences in the reduction of the HAD score at 3 months between the duloxetine group and the Doxazosin group, and there were significant differences in the reduction of the HAD score at 6 months among the groups (P < 0.05). The incidence rates of adverse reactions in the duloxetine group, the sertraline group, and the duloxetine group were 29.5%, 17%, and 7.3%, respectively, with adverse events ranging from mild to moderate.There was a clear relationship between the extent of pain and mental factors in CP/CPPS with the main symptom of pain. Doxazosin combined with duloxetine exhibited good safety and efficacy in the treatment of pain disorder in CP/CPPS.

Description

Doxazosin (UK 33274) is a quinazoline-derivative that selectively antagonizes postsynaptic α1-adrenergic receptors.

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