You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDoxazosin
Accession NumberDB00590  (APRD00474)
TypeSmall Molecule
GroupsApproved
Description

Doxazosin is a quinazoline-derivative that selectively antagonizes postsynaptic α1-adrenergic receptors. It may be used to mild to moderate hypertension and in the management of symptomatic benign prostatic hyperplasia (BPH). α1-Receptors mediate contraction and hypertrophic growth of smooth muscle cells. Antagonism of these receptors leads to smooth muscle relaxation in the peripheral vasculature and prostate gland.

Structure
Thumb
Synonyms
1-(4-Amino-6,7-dimethoxy-2-chinazolinyl)-4-(2,3-dihydro-1,4-benzodioxixin-2-ylcarbonyl)piperazin
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazin
Doxazosin
Doxazosin mesilate
Doxazosin mesylate
Doxazosina
Doxazosine
Doxazosinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carduratablet8 mg/1oralRoerig1990-11-02Not applicableUs
Carduratablet4 mg/1oralRoerig1990-11-02Not applicableUs
Carduratablet2 mg/1oralRoerig1990-11-02Not applicableUs
Carduratablet1 mg/1oralRoerig1990-11-02Not applicableUs
Cardura XLtablet, multilayer, extended release4 mg/1oralRoerig2005-02-22Not applicableUs
Cardura XLtablet, multilayer, extended release8 mg/1oralRoerig2005-02-22Not applicableUs
Cardura-1 Tab 1mgtablet1 mgoralPfizer Canada Inc1992-12-31Not applicableCanada
Cardura-2 Tab 2mgtablet2 mgoralPfizer Canada Inc1992-12-31Not applicableCanada
Cardura-4 Tab 4mgtablet4 mgoralPfizer Canada Inc1992-12-31Not applicableCanada
Dom-doxazosintablet4 mgoralDominion Pharmacal2004-05-26Not applicableCanada
Dom-doxazosintablet2 mgoralDominion Pharmacal2004-05-26Not applicableCanada
Dom-doxazosintablet1 mgoralDominion Pharmacal2004-05-26Not applicableCanada
Doxazosin Mesylatetablet4 mg/1oralGreenstone LLC2014-07-07Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralGreenstone LLC2014-07-07Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralGreenstone LLC2014-07-07Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralREMEDYREPACK INC.2016-01-14Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralREMEDYREPACK INC.2015-11-12Not applicableUs
Doxazosin Mesylatetablet8 mg/1oralGreenstone LLC2014-07-07Not applicableUs
Doxazosin-1tablet1 mgoralPro Doc Limitee2000-05-10Not applicableCanada
Doxazosin-2tablet2 mgoralPro Doc Limitee2000-05-10Not applicableCanada
Doxazosin-4tablet4 mgoralPro Doc Limitee2000-05-10Not applicableCanada
Mylan-doxazosintablet2 mgoralMylan Pharmaceuticals Ulc1999-07-16Not applicableCanada
Mylan-doxazosintablet4 mgoralMylan Pharmaceuticals Ulc1999-07-16Not applicableCanada
Mylan-doxazosintablet1 mgoralMylan Pharmaceuticals Ulc1999-07-16Not applicableCanada
PMS-doxazosintablet2 mgoralPharmascience Inc2001-10-01Not applicableCanada
PMS-doxazosintablet1 mgoralPharmascience Inc2001-10-01Not applicableCanada
PMS-doxazosintablet4 mgoralPharmascience Inc2001-10-01Not applicableCanada
Ratio-doxazosintablet4 mgoralRatiopharm Inc Division Of Teva Canada Limited2001-02-132006-08-04Canada
Ratio-doxazosintablet2 mgoralRatiopharm Inc Division Of Teva Canada Limited2001-02-132006-08-04Canada
Ratio-doxazosintablet1 mgoralRatiopharm Inc Division Of Teva Canada Limited2001-02-132006-08-04Canada
Teva-doxazosintablet4 mgoralTeva Canada Limited2000-09-01Not applicableCanada
Teva-doxazosintablet2 mgoralTeva Canada Limited2000-09-01Not applicableCanada
Teva-doxazosintablet1 mgoralTeva Canada Limited2000-09-01Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-doxazosintablet4 mgoralApotex Inc1999-07-22Not applicableCanada
Apo-doxazosintablet2 mgoralApotex Inc1999-07-22Not applicableCanada
Apo-doxazosintablet1 mgoralApotex Inc1999-07-22Not applicableCanada
Doxazosintablet4 mg/1oralPd Rx Pharmaceuticals, Inc.2011-10-27Not applicableUs
Doxazosintablet1 mg/1oralAmerican Health Packaging2014-09-22Not applicableUs
Doxazosintablet8 mg/1oralbryant ranch prepack2011-05-27Not applicableUs
Doxazosintablet2 mg/1oralPreferred Pharmaceuticals, Inc.2013-06-24Not applicableUs
Doxazosintablet1 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-10-19Not applicableUs
Doxazosintablet8 mg/1oralTeva Pharmaceuticals USA Inc2014-12-06Not applicableUs
Doxazosintablet4 mg/1oralAv Kare, Inc.2015-04-09Not applicableUs
Doxazosintablet4 mg/1oralAccord Healthcare Inc.2015-03-24Not applicableUs
Doxazosintablet4 mg/1oralREMEDYREPACK INC.2013-03-14Not applicableUs
Doxazosintablet2 mg/1oralLake Erie Medical DBA Quality Care Products LLC2000-10-20Not applicableUs
Doxazosintablet8 mg/1oralAv Kare, Inc.2015-04-09Not applicableUs
Doxazosintablet2 mg/1oralPd Rx Pharmaceuticals, Inc.2011-10-27Not applicableUs
Doxazosintablet2 mg/1oralPhysicians Total Care, Inc.2003-05-28Not applicableUs
Doxazosintablet4 mg/1oralREMEDYREPACK INC.2015-12-10Not applicableUs
Doxazosintablet8 mg/1oralREMEDYREPACK INC.2013-05-132016-04-05Us
Doxazosintablet8 mg/1oralApotex Corp.2011-07-14Not applicableUs
Doxazosintablet4 mg/1oralPreferred Pharmaceuticals, Inc2011-03-08Not applicableUs
Doxazosintablet8 mg/1oralMajor Pharmaceuticals2011-07-14Not applicableUs
Doxazosintablet8 mg/1oralMylan Pharmaceuticals Inc.2000-10-20Not applicableUs
Doxazosintablet2 mg/1oralAv Kare, Inc.2015-04-09Not applicableUs
Doxazosintablet2 mg/1oralAccord Healthcare Inc.2015-03-24Not applicableUs
Doxazosintablet2 mg/1oralREMEDYREPACK INC.2013-02-252016-03-31Us
Doxazosintablet2 mg/1oralCardinal Health2011-08-18Not applicableUs
Doxazosintablet8 mg/1oralPhysicians Total Care, Inc.2003-04-03Not applicableUs
Doxazosintablet2 mg/1oralREMEDYREPACK INC.2015-11-12Not applicableUs
Doxazosintablet4 mg/1oralApotex Corp.2011-07-14Not applicableUs
Doxazosintablet2 mg/1oralPreferred Pharmaceuticals, Inc2011-03-08Not applicableUs
Doxazosintablet8 mg/1oralAphena Pharma Solutions Tennessee, Llc2000-10-20Not applicableUs
Doxazosintablet2 mg/1oralRebel Distributors Corp2011-03-08Not applicableUs
Doxazosintablet1 mg/1oralAccord Healthcare Inc.2015-03-04Not applicableUs
Doxazosintablet4 mg/1oralMylan Institutional Inc.2001-01-01Not applicableUs
Doxazosintablet4 mg/1oralCardinal Health2011-08-18Not applicableUs
Doxazosintablet4 mg/1oralREMEDYREPACK INC.2015-06-01Not applicableUs
Doxazosintablet2 mg/1oralApotex Corp.2011-07-14Not applicableUs
Doxazosintablet8 mg/1oralLegacy Pharmaceutical Packaging2011-07-14Not applicableUs
Doxazosintablet4 mg/1oralMajor Pharmaceuticals2011-07-14Not applicableUs
Doxazosintablet4 mg/1oralMylan Pharmaceuticals Inc.2000-10-20Not applicableUs
Doxazosintablet2 mg/1oralMylan Institutional Inc.2001-01-01Not applicableUs
Doxazosintablet1 mg/1oralCardinal Health2011-08-18Not applicableUs
Doxazosintablet4 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Doxazosintablet1 mg/1oralApotex Corp.2011-07-14Not applicableUs
Doxazosintablet4 mg/1oralLegacy Pharmaceutical Packaging2011-07-14Not applicableUs
Doxazosintablet2 mg/1oralMajor Pharmaceuticals2011-07-14Not applicableUs
Doxazosintablet2 mg/1oralMylan Pharmaceuticals Inc.2000-10-20Not applicableUs
Doxazosintablet8 mg/1oralLake Erie Medical DBA Quality Care Products LLC2000-10-20Not applicableUs
Doxazosintablet4 mg/1oralStat Rx USA2009-10-27Not applicableUs
Doxazosintablet4 mg/1oralCardinal Health2000-10-20Not applicableUs
Doxazosintablet1 mg/1oralREMEDYREPACK INC.2014-12-01Not applicableUs
Doxazosintablet2 mg/1oralLegacy Pharmaceutical Packaging2011-07-14Not applicableUs
Doxazosintablet1 mg/1oralMajor Pharmaceuticals2011-07-14Not applicableUs
Doxazosintablet1 mg/1oralMylan Pharmaceuticals Inc.2000-10-20Not applicableUs
Doxazosintablet4 mg/1oralLake Erie Medical DBA Quality Care Products LLC2000-10-20Not applicableUs
Doxazosintablet1 mg/1oralMylan Institutional Inc.2001-01-01Not applicableUs
Doxazosintablet2 mg/1oralCardinal Health2000-10-20Not applicableUs
Doxazosintablet8 mg/1oralSt Marys Medical Park Pharmacy2014-04-21Not applicableUs
Doxazosintablet4 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-10-19Not applicableUs
Doxazosintablet1 mg/1oralTeva Pharmaceuticals USA Inc2014-08-12Not applicableUs
Doxazosintablet4 mg/1oralAidarex Pharmaceuticals LLC2011-10-27Not applicableUs
Doxazosintablet8 mg/1oralUnit Dose Services2000-10-20Not applicableUs
Doxazosintablet1 mg/1oralPhysicians Total Care, Inc.2003-08-14Not applicableUs
Doxazosintablet2 mg/1oralSt Marys Medical Park Pharmacy2014-04-21Not applicableUs
Doxazosintablet4 mg/1oralAmerican Health Packaging2014-09-22Not applicableUs
Doxazosintablet2 mg/1oralbryant ranch prepack2011-03-08Not applicableUs
Doxazosintablet2 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-10-19Not applicableUs
Doxazosintablet2 mg/1oralTeva Pharmaceuticals USA Inc2014-08-12Not applicableUs
Doxazosintablet4 mg/1oralREMEDYREPACK INC.2013-05-23Not applicableUs
Doxazosintablet4 mg/1oralUnit Dose Services2000-10-20Not applicableUs
Doxazosintablet4 mg/1oralAphena Pharma Solutions Tennessee, Llc2000-10-20Not applicableUs
Doxazosintablet4 mg/1oralPhysicians Total Care, Inc.2003-05-28Not applicableUs
Doxazosintablet2 mg/1oralREMEDYREPACK INC.2014-02-03Not applicableUs
Doxazosintablet4 mg/1oralSt Marys Medical Park Pharmacy2013-05-02Not applicableUs
Doxazosintablet2 mg/1oralAmerican Health Packaging2014-09-22Not applicableUs
Doxazosintablet4 mg/1oralbryant ranch prepack2011-03-08Not applicableUs
Doxazosintablet8 mg/1oralTeva Pharmaceuticals USA Inc2000-10-202015-10-31Us
Doxazosintablet8 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-10-19Not applicableUs
Doxazosintablet4 mg/1oralTeva Pharmaceuticals USA Inc2014-09-12Not applicableUs
Doxazosintablet8 mg/1oralAccord Healthcare Inc.2015-03-24Not applicableUs
Doxazosintablet8 mg/1oralUnit Dose Services2000-10-20Not applicableUs
Doxazosintablet2 mg/1oralAphena Pharma Solutions Tennessee, Llc2000-10-20Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralMajor Pharmaceuticals2010-05-06Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralMajor Pharmaceuticals2010-04-28Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralREMEDYREPACK INC.2011-11-16Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralREMEDYREPACK INC.2011-06-06Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralState of Florida DOH Central Pharmacy2014-11-01Not applicableUs
Doxazosin Mesylatetablet8 mg/1oralDAVA Pharmaceuticals, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralREMEDYREPACK INC.2011-03-31Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralREMEDYREPACK INC.2015-04-14Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralDAVA Pharmaceuticals, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Doxazosin Mesylatetablet8 mg/1oralGolden State Medical Supply, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralDAVA Pharmaceuticals, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralBlenheim Pharmacal, Inc.2013-12-10Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralREMEDYREPACK INC.2011-05-09Not applicableUs
Doxazosin Mesylatetablet8 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralGolden State Medical Supply, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralDispensing Solutions, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralDAVA Pharmaceuticals, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralBlenheim Pharmacal, Inc.2013-12-10Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralREMEDYREPACK INC.2010-07-29Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralREMEDYREPACK INC.2014-05-27Not applicableUs
Doxazosin Mesylatetablet2 mg/1oralGolden State Medical Supply, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet8 mg/1oralMajor Pharmaceuticals2010-04-28Not applicableUs
Doxazosin Mesylatetablet1 mg/1oralGolden State Medical Supply, Inc.2004-06-10Not applicableUs
Doxazosin Mesylatetablet4 mg/1oralMajor Pharmaceuticals2010-04-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AlfadilPfizer (Sweden)
CardenalinPfizer (Japan; discontinued)
CardularPfizer (Germany)
Cardura-1Pfizer (Canada)
Cardura-2Pfizer (Canada)
Cardura-4Pfizer (Canada)
CarduranPfizer (Brazil, Denmark, Norway, Spain)
DiblocinAstraZeneca (Germany)
NormothenBioindustria (Italy)
SupressinPfizer (Austria)
Brand mixtures
NameLabellerIngredients
Cardura-1,2,and 4Astrazeneca Canada Inc
SaltsNot Available
Categories
UNIINW1291F1W8
CAS number74191-85-8
WeightAverage: 451.4751
Monoisotopic: 451.185568935
Chemical FormulaC23H25N5O5
InChI KeyInChIKey=RUZYUOTYCVRMRZ-UHFFFAOYSA-N
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)
IUPAC Name
2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine
SMILES
COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1COC2=CC=CC=C2O1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Quinazolinamine
  • Quinazoline
  • Benzodioxane
  • Benzo-p-dioxin
  • Benzo-1,4-dioxane
  • Dialkylarylamine
  • Anisole
  • Aminopyrimidine
  • Alkyl aryl ether
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • Primary aromatic amine
  • Para-dioxin
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor treatment and management of mild to moderate hypertension and urinary obstruction symptoms caused by BPH.
PharmacodynamicsDoxazosin is an alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Accordingly, Doxazosin is a selective inhibitor of the alpha1 subtype of alpha adrenergic receptors. In the human prostate, Doxazosin antagonizes phenylephrine (alpha1 agonist)-induced contractions, in vitro, and binds with high affinity to the alpha1c adrenoceptor, which is thought to be the predominant functional type in the prostate. Studies in normal human subjects have shown that Doxazosin competitively antagonized the pressor effects of phenylephrine (an alpha1 agonist) and the systolic pressor effect of norepinephrine. The antihypertensive effect of Doxazosin results from a decrease in systemic vascular resistance and the parent compound Doxazosin is primarily responsible for the antihypertensive activity.
Mechanism of actionDoxazosin acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation.
Related Articles
Absorption65%
Volume of distributionNot Available
Protein binding98%
Metabolism

Hepatic.

Route of eliminationOn average only 4.8% of the dose was excreted as unchanged drug in the feces and only a trace of the total radioactivity in the urine was attributed to unchanged drug.
Half life22 hours
ClearanceNot Available
ToxicitySymptoms of overdose include hypotension. Oral LD50 is greater than 1000 mg/kg in mice and rats.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9627
Caco-2 permeable+0.7863
P-glycoprotein substrateSubstrate0.7303
P-glycoprotein inhibitor INon-inhibitor0.7391
P-glycoprotein inhibitor IINon-inhibitor0.9528
Renal organic cation transporterNon-inhibitor0.6909
CYP450 2C9 substrateNon-substrate0.9011
CYP450 2D6 substrateNon-substrate0.8195
CYP450 3A4 substrateSubstrate0.7228
CYP450 1A2 substrateNon-inhibitor0.8293
CYP450 2C9 inhibitorNon-inhibitor0.9161
CYP450 2D6 inhibitorNon-inhibitor0.9533
CYP450 2C19 inhibitorNon-inhibitor0.9084
CYP450 3A4 inhibitorNon-inhibitor0.8002
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9078
Ames testNon AMES toxic0.5648
CarcinogenicityNon-carcinogens0.8905
BiodegradationNot ready biodegradable0.9854
Rat acute toxicity2.1954 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8602
hERG inhibition (predictor II)Inhibitor0.823
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pfizer inc
  • Pfizer laboratories div pfizer inc
  • Actavis elizabeth llc
  • Apotex inc
  • Dava pharmaceuticals inc
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Mylan pharmaceuticals inc
  • Pliva inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral1 mg/1
Tabletoral2 mg/1
Tabletoral4 mg/1
Tabletoral8 mg/1
Tablet, multilayer, extended releaseoral4 mg/1
Tablet, multilayer, extended releaseoral8 mg/1
Tabletoral1 mg
Kit; tabletoral
Tabletoral2 mg
Tabletoral4 mg
Prices
Unit descriptionCostUnit
Cardura XL 4 mg 24 Hour tablet2.22USD tablet
Cardura xl 8 mg tablet2.04USD tablet
Cardura xl 4 mg tablet1.94USD tablet
Cardura 8 mg tablet1.93USD tablet
Cardura 4 mg tablet1.89USD tablet
Cardura 2 mg tablet1.81USD tablet
Cardura 1 mg tablet1.72USD tablet
Doxazosin mesylate 8 mg tablet1.04USD tablet
Cardura 4 mg Tablet1.0USD tablet
Doxazosin mesylate 4 mg tablet0.99USD tablet
Doxazosin mesylate 1 mg tablet0.94USD tablet
Doxazosin mesylate 2 mg tablet0.94USD tablet
Cardura 2 mg Tablet0.77USD tablet
Cardura 1 mg Tablet0.64USD tablet
Apo-Doxazosin 4 mg Tablet0.56USD tablet
Mylan-Doxazosin 4 mg Tablet0.56USD tablet
Novo-Doxazosin 4 mg Tablet0.56USD tablet
Pms-Doxazosin 4 mg Tablet0.56USD tablet
Apo-Doxazosin 2 mg Tablet0.43USD tablet
Mylan-Doxazosin 2 mg Tablet0.43USD tablet
Novo-Doxazosin 2 mg Tablet0.43USD tablet
Pms-Doxazosin 2 mg Tablet0.43USD tablet
Apo-Doxazosin 1 mg Tablet0.36USD tablet
Mylan-Doxazosin 1 mg Tablet0.36USD tablet
Novo-Doxazosin 1 mg Tablet0.36USD tablet
Pms-Doxazosin 1 mg Tablet0.36USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point289-290 °CNot Available
water solubility24 mg/LNot Available
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.79 mg/mLALOGPS
logP2.53ALOGPS
logP2.14ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.67ChemAxon
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area112.27 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.64 m3·mol-1ChemAxon
Polarizability46.63 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

K. S. Keshava Murthy, Gamini Weeratunga, Tianhao Zhou, Bhaskar Reddy Guntoori, “Process for the manufacture of intermediates suitable to make doxazosin, terazosin, prazosin, tiodazosin and related antihypertensive medicines.” U.S. Patent US5919931, issued September, 1986.

US5919931
General References
  1. Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. [PubMed:12461301 ]
External Links
ATC CodesC02CA04
AHFS Codes
  • 24:20.00
PDB EntriesNot Available
FDA labelDownload (511 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Doxazosin.
AlfuzosinAlfuzosin may increase the antihypertensive activities of Doxazosin.
AmifostineDoxazosin may increase the hypotensive activities of Amifostine.
AmlodipineDoxazosin may increase the hypotensive activities of Amlodipine.
AmrinoneDoxazosin may increase the hypotensive activities of Amrinone.
AprepitantThe serum concentration of Doxazosin can be increased when it is combined with Aprepitant.
BepridilDoxazosin may increase the hypotensive activities of Bepridil.
BexaroteneThe serum concentration of Doxazosin can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Doxazosin can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Doxazosin can be decreased when it is combined with Bosentan.
BrimonidineBrimonidine may increase the antihypertensive activities of Doxazosin.
ButabarbitalButabarbital may increase the hypotensive activities of Doxazosin.
ButethalButethal may increase the hypotensive activities of Doxazosin.
ConivaptanThe serum concentration of Doxazosin can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Doxazosin can be decreased when it is combined with Dabrafenib.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Doxazosin.
DasatinibThe serum concentration of Doxazosin can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Doxazosin can be decreased when it is combined with Deferasirox.
DiazoxideDiazoxide may increase the hypotensive activities of Doxazosin.
DipivefrinDoxazosin may decrease the vasoconstricting activities of Dipivefrin.
DuloxetineDoxazosin may increase the orthostatic hypotensive activities of Duloxetine.
FelodipineDoxazosin may increase the hypotensive activities of Felodipine.
FluconazoleThe metabolism of Doxazosin can be decreased when combined with Fluconazole.
FlunarizineDoxazosin may increase the hypotensive activities of Flunarizine.
FosaprepitantThe serum concentration of Doxazosin can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Doxazosin can be increased when it is combined with Fusidic Acid.
GabapentinDoxazosin may increase the hypotensive activities of Gabapentin.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Doxazosin.
HexobarbitalHexobarbital may increase the hypotensive activities of Doxazosin.
IdelalisibThe serum concentration of Doxazosin can be increased when it is combined with Idelalisib.
IsradipineDoxazosin may increase the hypotensive activities of Isradipine.
IvacaftorThe serum concentration of Doxazosin can be increased when it is combined with Ivacaftor.
LamotrigineDoxazosin may increase the hypotensive activities of Lamotrigine.
LercanidipineDoxazosin may increase the hypotensive activities of Lercanidipine.
LevodopaDoxazosin may increase the orthostatic hypotensive activities of Levodopa.
LuliconazoleThe serum concentration of Doxazosin can be increased when it is combined with Luliconazole.
Magnesium SulfateDoxazosin may increase the hypotensive activities of Magnesium Sulfate.
MethohexitalMethohexital may increase the hypotensive activities of Doxazosin.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Doxazosin.
MidodrineDoxazosin may decrease the vasoconstricting activities of Midodrine.
MifepristoneThe serum concentration of Doxazosin can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Doxazosin can be decreased when it is combined with Mitotane.
MolsidomineMolsidomine may increase the hypotensive activities of Doxazosin.
MoxonidineMoxonidine may increase the hypotensive activities of Doxazosin.
NadololNadolol may increase the orthostatic hypotensive activities of Doxazosin.
NelfinavirThe metabolism of Doxazosin can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Doxazosin can be increased when it is combined with Netupitant.
NicardipineDoxazosin may increase the hypotensive activities of Nicardipine.
NicorandilNicorandil may increase the hypotensive activities of Doxazosin.
NimodipineDoxazosin may increase the hypotensive activities of Nimodipine.
NisoldipineDoxazosin may increase the hypotensive activities of Nisoldipine.
NitrendipineDoxazosin may increase the hypotensive activities of Nitrendipine.
ObinutuzumabDoxazosin may increase the hypotensive activities of Obinutuzumab.
PalbociclibThe serum concentration of Doxazosin can be increased when it is combined with Palbociclib.
PentobarbitalPentobarbital may increase the hypotensive activities of Doxazosin.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Doxazosin.
PerhexilineDoxazosin may increase the hypotensive activities of Perhexiline.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Doxazosin.
PhenytoinThe metabolism of Doxazosin can be increased when combined with Phenytoin.
PrazosinPrazosin may increase the antihypertensive activities of Doxazosin.
PrenylamineDoxazosin may increase the hypotensive activities of Prenylamine.
PrimidonePrimidone may increase the hypotensive activities of Doxazosin.
QuinineQuinine may increase the hypotensive activities of Doxazosin.
RisedronateDoxazosin may increase the hypotensive activities of Risedronate.
RisperidoneDoxazosin may increase the hypotensive activities of Risperidone.
RituximabDoxazosin may increase the hypotensive activities of Rituximab.
SecobarbitalSecobarbital may increase the hypotensive activities of Doxazosin.
SiltuximabThe serum concentration of Doxazosin can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Doxazosin can be increased when it is combined with Simeprevir.
St. John's WortThe serum concentration of Doxazosin can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Doxazosin can be increased when it is combined with Stiripentol.
TadalafilTadalafil may increase the hypotensive activities of Doxazosin.
TocilizumabThe serum concentration of Doxazosin can be decreased when it is combined with Tocilizumab.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Doxazosin.
TreprostinilTreprostinil may increase the hypotensive activities of Doxazosin.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Doxazosin.
VardenafilVardenafil may increase the hypotensive activities of Doxazosin.
VerapamilDoxazosin may increase the hypotensive activities of Verapamil.
YohimbineYohimbine may decrease the antihypertensive activities of Doxazosin.
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Yono M, Foster HE Jr, Shin D, Takahashi W, Pouresmail M, Latifpour J: Doxazosin-induced up-regulation of alpha 1A-adrenoceptor mRNA in the rat lower urinary tract. Can J Physiol Pharmacol. 2004 Oct;82(10):872-8. [PubMed:15573147 ]
  2. Michel MC, Grubbel B, Taguchi K, Verfurth F, Otto T, Kropfl D: Drugs for treatment of benign prostatic hyperplasia: affinity comparison at cloned alpha 1-adrenoceptor subtypes and in human prostate. J Auton Pharmacol. 1996 Feb;16(1):21-8. [PubMed:8736427 ]
  3. Roehrborn CG, Schwinn DA: Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia. J Urol. 2004 Mar;171(3):1029-35. [PubMed:14767264 ]
  4. Ishizuka O, Pandita RK, Mattiasson A, Steers WD, Andersson KE: Stimulation of bladder activity by volume, L-dopa and capsaicin in normal conscious rats--effects of spinal alpha 1-adrenoceptor blockade. Naunyn Schmiedebergs Arch Pharmacol. 1997 Jun;355(6):787-93. [PubMed:9205965 ]
  5. Bae JH, Jung PB, Lee JG: The effects of alpha-adrenoceptor antagonists on the urethral perfusion pressure of the female rat. BJU Int. 2005 Nov;96(7):1131-5. [PubMed:16225542 ]
  6. Greco KA, McVary KT: The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43. doi: 10.1038/ijir.2008.51. [PubMed:19002123 ]
  7. Shannon R, Chaudhry M: Effect of alpha1-adrenergic receptors in cardiac pathophysiology. Am Heart J. 2006 Nov;152(5):842-50. [PubMed:17070143 ]
  8. Martin DJ: Preclinical pharmacology of alpha1-adrenoceptor antagonists. Eur Urol. 1999;36 Suppl 1:35-41; discussion 65. [PubMed:10393471 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Lepor H: Alpha blockers for the treatment of benign prostatic hyperplasia. Rev Urol. 2007 Fall;9(4):181-90. [PubMed:18231614 ]
  2. Greco KA, McVary KT: The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43. doi: 10.1038/ijir.2008.51. [PubMed:19002123 ]
  3. Shannon R, Chaudhry M: Effect of alpha1-adrenergic receptors in cardiac pathophysiology. Am Heart J. 2006 Nov;152(5):842-50. [PubMed:17070143 ]
  4. Martin DJ: Preclinical pharmacology of alpha1-adrenoceptor antagonists. Eur Urol. 1999;36 Suppl 1:35-41; discussion 65. [PubMed:10393471 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Lepor H: Alpha blockers for the treatment of benign prostatic hyperplasia. Rev Urol. 2007 Fall;9(4):181-90. [PubMed:18231614 ]
  2. Greco KA, McVary KT: The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43. doi: 10.1038/ijir.2008.51. [PubMed:19002123 ]
  3. Shannon R, Chaudhry M: Effect of alpha1-adrenergic receptors in cardiac pathophysiology. Am Heart J. 2006 Nov;152(5):842-50. [PubMed:17070143 ]
  4. Martin DJ: Preclinical pharmacology of alpha1-adrenoceptor antagonists. Eur Urol. 1999;36 Suppl 1:35-41; discussion 65. [PubMed:10393471 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity
Specific Function:
Pore-forming (alpha) subunit of voltage-gated potassium channel. Elicits a slowly activating, rectifying current (By similarity). Channel properties may be modulated by cAMP and subunit assembly.
Gene Name:
KCNH6
Uniprot ID:
Q9H252
Molecular Weight:
109923.705 Da
References
  1. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity
Specific Function:
Pore-forming (alpha) subunit of voltage-gated potassium channel. Channel properties may be modulated by cAMP and subunit assembly.
Gene Name:
KCNH7
Uniprot ID:
Q9NS40
Molecular Weight:
134998.525 Da
References
  1. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Not Available
Specific Function:
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
Molecular Weight:
23511.38 Da
References
  1. Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. [PubMed:2870173 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100 ]
  2. Takara K, Sakaeda T, Kakumoto M, Tanigawara Y, Kobayashi H, Okumura K, Ohnishi N, Yokoyama T: Effects of alpha-adrenoceptor antagonist doxazosin on MDR1-mediated multidrug resistance and transcellular transport. Oncol Res. 2009;17(11-12):527-33. [PubMed:19806783 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11