2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; methanesulfonic acid

• ChemBase ID: 72624
• Molecular Formular: C24H29N5O8S
• Molecular Mass: 547.58076
• Monoisotopic Mass: 547.17368391
• SMILES: c12cc(c(cc1c(nc(n2)N1CCN(CC1)C(=O)C1COc2c(O1)cccc2)N)OC)OC.S(=O)(=O)(O)C
• Canonical SMILES: CS(=O)(=O)O.COc1cc2nc(nc(c2cc1OC)N)N1CCN(CC1)C(=O)C1COc2c(O1)cccc2
• InChI: 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)
• InChIKey: VJECBOKJABCYMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; methanesulfonic acid
• IUPAC Traditional name: 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; methanesulfonic acid; 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine mesylate; doxazosin; methanesulfonic acid
• Synonyms: Alfadil; Cardenalin; Cardular; Diblocin; Normothen; Supressin; Cardura; Carduran; Cardura XL; Doxazosin mesylate; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[4-(1,4-benzodioxan-2-yl)carpiperazin-1-yl)]-6,7-dimethoxyquinazoline mesylate; Doxazosin mesylate; 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; methanesulfonic acid

Database IDs

• CAS Number: 74191-85-8; 77883-43-3
• MDL Number: MFCD00216023
• PubChem SID: 162037549; 24278398
• PubChem CID: 62978

CALCULATED PROPERTIES

• Acid pKa: 12.670158
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 0.6322931
• LogD (pH = 7.4): 1.9103665
• Log P: 2.135759
• Molar Refractivity: 121.6383 cm^3
• Polarizability: 46.96491 Å^3
• Polar Surface Area: 112.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: white powder
• Melting Point: 279 - 281°C
• Hydrophobicity(logP): 3.532

Safety Information

• Storage Condition: -20°C
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: adrenergic receptor
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146)rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)
• Mechanism of Action: alpha-1-Adrenoceptor antagonist; Alters serum lipid profile via increase in LDL-receptor activity and other effects

Product Information

• Purity: ≥97% (HPLC); 95%
• Salt Data: Mesylate
• Application(s): Antihypertensive agent; Used in the treatment of benign prostatic hyperplasia
• Empirical Formula (Hill Notation): C23H25N5O5 · CH3SO3H

DETAILS

Selleck Chemicals - S1324

Research Area: Cardiovascular Disease
Biological Activity:
Doxazosin mesylate , a quinazoline compound, is an alpha-1 adrenergic receptor blocker used to treat high blood pressure and benign prostatic hyperplasia. It inhibits the binding of norepinephrine to the alpha-1 receptors on the membrane of vascular smooth muscle cells. The primary effect of this inhibition is relaxed vascular smooth muscle tone (vasodilation), which decreases peripheral vascular resistance, leading to decreased blood pressure. [1]

Sigma Aldrich - D9815

Biochem/physiol Actions
α1-adrenoceptor antagonist; relaxes smooth muscles of the prostate

REFERENCES

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