Doxazosin Mesylate (UK 33274 mesylate)

Alias: UK-33274 mesylate; UK33274 mesylate; UK 33274 mesylate

Cat No.:V1096 Purity: ≥98%

COA Product Data Instructions for use SDS

Doxazosin Mesylate (UK 33274 mesylate) Chemical Structure CAS No.: 77883-43-3
Product category: Adrenergic Receptor

This product is for research use only, not for human use. We do not sell to patients.

Size	Price	Stock	Qty
500mg
1g
2g
5g
10g
25g
Other Sizes

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Other Forms of Doxazosin Mesylate (UK 33274 mesylate):

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Doxazosin mesylate (formerly UK-33274; UK 33274; trade names Cardura), the mesylate salt of Doxazosin which is a quinazoline-derivative, is a potent and selective antagonist of postsynaptic α1-adrenergic receptors (so called alpha-blockers) with anti-hypertensive effects. It can be used to treat benign prostatic hyperplasia-related high blood pressure and urinary retention. By blocking the binding of norepinephrine to the α-1 receptors on the membrane of vascular smooth muscle cells, doxazosin prevents the release of norepinephrine from sympathetic nerve terminals. The therapy of benign prostatic hyperplasia may be partially attributed to doxazosin's strong affinity for the alpha-1c adrenoceptor, which is the primary functional type in the prostate.

Biological Activity I Assay Protocols (From Reference)

Targets

α1-adrenergic receptor

ln Vitro

In vitro activity: Doxazosin-induced apoptosis is inhibited by particular caspase-8 inhibitors, indicating that caspase-8 functions as a functional mediator of doxazosin-induced apoptosis. Doxazosin causes an increase in FADD recruitment and caspase-8 activation, which suggests that the mechanism behind Doxazosin's action on prostate cells is Fas-mediated apoptosis.[1] The average reduction in plasma total, LDL plus VLDL, and total triglyceride levels is 46%, 61%, and 45%, respectively, for doxazosin and cholestyramine.[2] In the HL-1 cell line, doxazosin causes DNA damage and cell death. In primary cultures of neonatal rat cardiomyocytes, doxazosin treatment reduces cell viability; in primary cultures of adult human cardiomyocytes, doxazosin-induced apoptosis is shown by Hoechst dye vital staining.[3] Doxazosin inhibits cell migration and impedes cell adhesion to surfaces coated with collagen and fibronectin, potentially through downregulating VEGF expression, thereby counteracting the VEGF-mediated angiogenic response of HUVEC cells.[4]

ln Vivo

Doxazosin additionally lowers mean arterial pressure in hamsters by 18% without changing heart rate.[2] Doxazosin significantly lowers the wet weight of mouse prostate reconstitution (MPR) infected with BabeTGF-beta 1.[5]

Animal Protocol

References

[1]. Cancer Res . 2006 Jan 1;66(1):464-72.

[2]. Atherosclerosis . 1991 Nov;91(1-2):35-49.

[3]. Circulation . 2003 Jan 7;107(1):127-31.

[4]. J Cell Biochem . 2005 Feb 1;94(2):374-88.

[5]. Prostate . 1997 Nov 1;33(3):157-63.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C24H29N5O8S

Molecular Weight

547.58

Exact Mass

547.17

Elemental Analysis

C, 52.64; H, 5.34; N, 12.79; O, 23.37; S, 5.85

CAS #

77883-43-3

Related CAS #

Doxazosin; 74191-85-8; Doxazosin-d8 hydrochloride; 1219803-95-8

Appearance

Solid powder

SMILES

COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4)N)OC.CS(=O)(=O)O

InChi Key

VJECBOKJABCYMF-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H25N5O5.CH4O3S/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;1-5(2,3)4/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26);1H3,(H,2,3,4）

Chemical Name

[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone;methanesulfonic acid

Synonyms

UK-33274 mesylate; UK33274 mesylate; UK 33274 mesylate

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 15~33.3 mg/mL (27.4~60.9 mM)

Water: <1 mg/mL

Ethanol: <1 mg/mL

Solubility (In Vivo)

Chemical Name:(4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanone methanesulfonate

InChi Key:VJECBOKJABCYMF-UHFFFAOYSA-N

InChi Code:InChI=1S/C23H25N5O5.CH4O3S/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;1-5(2,3)4/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26);1H3,(H,2,3,4)

SMILES Code:O=C(N1CCN(C2=NC(N)=C3C=C(OC)C(OC)=CC3=N2)CC1)C4COC5=CC=CC=C5O4.OS(=O)(C)=O

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8262 mL	9.1311 mL	18.2622 mL
	5 mM	0.3652 mL	1.8262 mL	3.6524 mL
	10 mM	0.1826 mL	0.9131 mL	1.8262 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT03339258	Recruiting	Drug: Placebo Drug: Doxazosin Mesylate, Extended Release	Stress Disorders, Post-Traumatic	San Francisco Veterans Affairs Medical Center	April 15, 2018	Phase 2
NCT05360953	Recruiting	Drug: Clonidine Drug: Doxazosin Drug: Placebo	Posttraumatic Stress Disorder	Charite University, Berlin, Germany	April 6, 2022	Phase 2
NCT04135846	Recruiting	Drug: Doxazosin Drug: Placebo	Alcohol Use Disorder (AUD)	Brown University	December 19, 2019	Phase 2
NCT01062945	Completed	Drug: Placebo Drug: Doxazosin	Cocaine Addiction Cocaine Abuse Cocaine Dependence Substance Abuse	Scripps Health	January 2010	Phase 1
NCT01145183	Completed	Drug: Placebo Drug: Doxazosin	Cocaine Dependence	Baylor College of Medicine	March 2010	Phase 2

Biological Data

Effect of doxazosin on cell viability and apoptosis of malignant and benign prostate epithelial cells. Subconfluent cultures of PC-3 and BPH-1 cells were exposed to increasing concentrations of doxazosin (0–35 μmol/L) and cell death was determined using the MTT assay (A) or stained with Hoechst (B); apoptotic cells were visualized and counted as described in Materials and Methods. Cancer Res . 2006 Jan 1;66(1):464-72.

Doxazosin causes an increase in Bax protein and induces caspase-8 activation in benign and malignant prostate epithelial cells. Cancer Res . 2006 Jan 1;66(1):464-72.
Suppression of doxazosin-induced apoptosis by caspase-8 inhibitor. Cancer Res . 2006 Jan 1;66(1):464-72.
Effect of doxazosin on the viability of HL-1 cardiomyocytes or NIH 3T3 cells. Circulation . 2003 Jan 7;107(1):127-31.
Effect of doxazosin on primary cultures of cardiomyocytes. Circulation . 2003 Jan 7;107(1):127-31.