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Identification
NameTerazosin
Accession NumberDB01162  (APRD00667)
TypeSmall Molecule
GroupsApproved
Description

Terazosin is a selective alpha1-antagonist used for treatment of symptoms of benign prostatic hyperplasia (BPH). It also acts to lower blood pressure, so it is a drug of choice for men with hypertension and prostate enlargement. It works by blocking the action of adrenaline on smooth muscle of the bladder and the blood vessel walls.

Structure
Thumb
Synonyms
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazine
Terazosin
Terazosina
Terazosine
Terazosinum
External Identifiers
  • Abbott 45975
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-terazosintablet2 mgoralDominion Pharmacal2001-10-31Not applicableCanada
Dom-terazosintablet10 mgoralDominion Pharmacal2001-10-31Not applicableCanada
Dom-terazosintablet1 mgoralDominion Pharmacal2001-10-31Not applicableCanada
Dom-terazosintablet5 mgoralDominion Pharmacal2001-10-31Not applicableCanada
Hytrintablet10 mgoralBgp Pharma Ulc1992-12-312016-02-19Canada
Hytrintablet5 mgoralBgp Pharma Ulc1989-12-31Not applicableCanada
Hytrintablet2 mgoralBgp Pharma Ulc1989-12-312016-02-19Canada
Hytrintablet1 mgoralBgp Pharma Ulc1989-12-312016-02-19Canada
Mylan-terazosintablet2 mgoralMylan Pharmaceuticals Ulc2012-11-092016-06-28Canada
Mylan-terazosintablet10 mgoralMylan Pharmaceuticals Ulc2012-11-092016-06-28Canada
Mylan-terazosintablet1 mgoralMylan Pharmaceuticals Ulc2012-11-092016-06-28Canada
Mylan-terazosintablet5 mgoralMylan Pharmaceuticals Ulc2012-11-092016-06-28Canada
Ntp-terazosintablet10 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-terazosintablet5 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-terazosintablet2 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-terazosintablet1 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Nu-terazosintablet5 mgoralNu Pharm Inc1998-03-052012-09-04Canada
Nu-terazosintablet2 mgoralNu Pharm Inc1998-03-052012-09-04Canada
Nu-terazosintablet1 mgoralNu Pharm Inc1998-03-052012-09-04Canada
Nu-terazosin 10 Mg Tabletstablet10 mgoralNu Pharm Inc1998-03-052012-09-04Canada
PHL-terazosintablet10 mgoralPharmel Inc2004-08-04Not applicableCanada
PHL-terazosintablet5 mgoralPharmel Inc2004-08-04Not applicableCanada
PHL-terazosintablet2 mgoralPharmel Inc2004-08-04Not applicableCanada
PHL-terazosintablet1 mgoralPharmel Inc2004-08-04Not applicableCanada
PMS-terazosintablet10 mgoralPharmascience Inc2001-02-23Not applicableCanada
PMS-terazosintablet5 mgoralPharmascience Inc2001-02-23Not applicableCanada
PMS-terazosintablet2 mgoralPharmascience Inc2001-02-23Not applicableCanada
PMS-terazosintablet1 mgoralPharmascience Inc2001-02-23Not applicableCanada
Ratio-terazosin - Tab 10mgtablet10 mgoralRatiopharm Inc Division Of Teva Canada Limited1997-10-312014-09-19Canada
Ratio-terazosin - Tab 1mgtablet1 mgoralRatiopharm Inc Division Of Teva Canada Limited1997-10-312014-09-19Canada
Ratio-terazosin - Tab 2mgtablet2 mgoralRatiopharm Inc Division Of Teva Canada Limited1997-10-312014-09-19Canada
Ratio-terazosin - Tab 5mgtablet5 mgoralRatiopharm Inc Division Of Teva Canada Limited1997-10-312014-09-19Canada
Riva-terazosin 1 Mg Tabletstablet1 mgoralLaboratoire Riva Inc1999-08-312003-07-28Canada
Riva-terazosin 10 Mg Tabletstablet10 mgoralLaboratoire Riva Inc1999-08-312003-07-28Canada
Riva-terazosin 2 Mg Tabletstablet2 mgoralLaboratoire Riva Inc1999-08-312003-07-28Canada
Riva-terazosin 5 Mg Tabletstablet5 mgoralLaboratoire Riva Inc1999-08-312003-07-28Canada
Terazosintablet1 mgoralSanis Health Inc2010-05-12Not applicableCanada
Terazosintablet10 mgoralSanis Health Inc2010-05-12Not applicableCanada
Terazosintablet5 mgoralSanis Health Inc2010-05-12Not applicableCanada
Terazosintablet2 mgoralSanis Health Inc2010-05-12Not applicableCanada
Terazosin-1tablet1 mgoralPro Doc Limitee1998-06-02Not applicableCanada
Terazosin-10tablet10 mgoralPro Doc Limitee1998-06-02Not applicableCanada
Terazosin-2tablet2 mgoralPro Doc Limitee1998-06-02Not applicableCanada
Terazosin-5tablet5 mgoralPro Doc Limitee1998-06-02Not applicableCanada
Teva-terazosintablet1 mgoralTeva Canada Limited1998-02-09Not applicableCanada
Teva-terazosintablet10 mgoralTeva Canada Limited1998-02-09Not applicableCanada
Teva-terazosintablet5 mgoralTeva Canada Limited1998-02-09Not applicableCanada
Teva-terazosintablet2 mgoralTeva Canada Limited1998-02-09Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-terazosintablet10 mgoralApotex Inc1997-09-26Not applicableCanada
Apo-terazosintablet5 mgoralApotex Inc1997-09-26Not applicableCanada
Apo-terazosintablet2 mgoralApotex Inc1997-09-26Not applicableCanada
Apo-terazosintablet1 mgoralApotex Inc1997-09-26Not applicableCanada
Tarazosincapsule1 mg/1oralMylan Institutional Inc.2000-04-01Not applicableUs
Tarazosincapsule5 mg/1oralMylan Institutional Inc.2000-04-01Not applicableUs
Tarazosincapsule2 mg/1oralMylan Institutional Inc.2000-04-01Not applicableUs
Terazosincapsule5 mg/1oralJubilant Cadista Pharmaceuticals Inc.2004-12-20Not applicableUs
Terazosincapsule1 mg/1oralApotex Corp.2001-04-12Not applicableUs
Terazosincapsule1 mg/1oralAidarex Pharmaceuticals LLC2001-04-12Not applicableUs
Terazosincapsule5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1998-03-03Not applicableUs
Terazosincapsule5 mg/1oralREMEDYREPACK INC.2013-09-19Not applicableUs
Terazosincapsule2 mg/1oralJubilant Cadista Pharmaceuticals Inc.2004-12-20Not applicableUs
Terazosincapsule5 mg/1oralPreferred Pharmaceuticals, Inc.2013-07-12Not applicableUs
Terazosincapsule2 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1998-03-30Not applicableUs
Terazosincapsule1 mg/1oralJubilant Cadista Pharmaceuticals Inc.2004-12-20Not applicableUs
Terazosincapsule10 mg/1oralBlenheim Pharmacal, Inc.2013-11-18Not applicableUs
Terazosincapsule5 mg/1oralProficient Rx LP2004-12-20Not applicableUs
Terazosincapsule5 mg/1oralNorthwind Pharmaceuticals, LLC2015-02-27Not applicableUs
Terazosincapsule2 mg/1oralNorthwind Pharmaceuticals, LLC2015-02-27Not applicableUs
Terazosincapsule10 mg/1oralApotex Corp.2001-04-12Not applicableUs
Terazosincapsule10 mg/1oralAidarex Pharmaceuticals LLC2001-04-12Not applicableUs
Terazosincapsule1 mg/1oralState of Florida DOH Central Pharmacy2014-11-01Not applicableUs
Terazosincapsule5 mg/1oralApotex Corp.2001-04-12Not applicableUs
Terazosincapsule1 mg/1oralREMEDYREPACK INC.2014-05-07Not applicableUs
Terazosincapsule10 mg/1oralJubilant Cadista Pharmaceuticals Inc.2004-12-21Not applicableUs
Terazosincapsule2 mg/1oralREMEDYREPACK INC.2013-03-28Not applicableUs
Terazosincapsule2 mg/1oralApotex Corp.2001-04-12Not applicableUs
Terazosincapsule10 mg/1oralProficient Rx LP2004-12-21Not applicableUs
Terazosincapsule2 mg/1oralAidarex Pharmaceuticals LLC2001-04-12Not applicableUs
Terazosincapsule10 mg/1oralbryant ranch prepack2004-12-21Not applicableUs
Terazosincapsule10 mg/1oralREMEDYREPACK INC.2013-09-19Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralPreferred Pharmaceuticals, Inc2012-04-05Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralRebel Distributors Corp2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralREMEDYREPACK INC.2011-11-10Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralPreferred Pharmaceuticals, Inc2012-04-05Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralPhysicians Total Care, Inc.2003-06-02Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralbryant ranch prepack2004-12-20Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralUnit Dose Services1998-03-30Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralREMEDYREPACK INC.2010-11-10Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralRebel Distributors Corp2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralREMEDYREPACK INC.2011-05-17Not applicableUs
Terazosin Hydrochloridecapsule10 mg/1oralPhysicians Total Care, Inc.2000-08-29Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralbryant ranch prepack2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralREMEDYREPACK INC.2013-05-132016-04-05Us
Terazosin Hydrochloridecapsule1 mg/1oralAphena Pharma Solutions Tennessee, Llc2004-12-20Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralREMEDYREPACK INC.2011-08-16Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralPhysicians Total Care, Inc.2000-08-29Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1998-03-30Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralSTAT Rx USA LLC2004-12-20Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralREMEDYREPACK INC.2011-07-29Not applicableUs
Terazosin Hydrochloridecapsule10 mg/1oralAphena Pharma Solutions Tennessee, Llc2004-12-21Not applicableUs
Terazosin Hydrochloridecapsule10 mg/1oralSandoz Inc1998-03-30Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralPhysicians Total Care, Inc.2000-09-05Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralREMEDYREPACK INC.2011-07-28Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralAphena Pharma Solutions Tennessee, Llc2004-12-20Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralSandoz Inc1998-03-30Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralCardinal Health2009-11-02Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralAphena Pharma Solutions Tennessee, Llc2004-12-20Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralSandoz Inc1998-03-30Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralREMEDYREPACK INC.2011-07-01Not applicableUs
Terazosin Hydrochloridecapsule2 mg/1oralPreferred Pharmaceuticals, Inc2012-04-05Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralCardinal Health2009-11-02Not applicableUs
Terazosin Hydrochloridecapsule1 mg/1oralSandoz Inc1998-03-30Not applicableUs
Terazosin Hydrochloridecapsule5 mg/1oralREMEDYREPACK INC.2011-06-09Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule10 mg/1oralMylan Pharmaceuticals Inc.2000-02-22Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule2 mg/1oralPd Rx Pharmaceuticals, Inc.2013-02-22Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule5 mg/1oralCardinal Health2011-01-28Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule5 mg/1oralMylan Pharmaceuticals Inc.2000-02-22Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule1 mg/1oralCardinal Health2011-01-28Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule2 mg/1oralMylan Pharmaceuticals Inc.2000-02-22Not applicableUs
Terazosin Hydrochloride Anhydrouscapsule1 mg/1oralMylan Pharmaceuticals Inc.2000-02-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BlavinBaliarda (Argentina)
FlumarcRaffo (Argentina)
FosfomicFinadiet (Argentina)
HeitrinAbbott (Germany; discontinued)
HytrinexAmdipharm (Sweden)
ItrinKeryos (Italy)
UrodieKeryos (Italy)
VicardAmdipharm (Austria)
ZayaselNot Available
Brand mixtures
NameLabellerIngredients
Hytrin-7 Tabs 1mg-7 Tabs 2mg-14 Tabs 5mgAbbott Laboratories, Limited
Salts
Name/CASStructureProperties
Terazosin Hydrochloride
Thumb
  • InChI Key: IWSWDOUXSCRCKW-UHFFFAOYNA-N
  • Monoisotopic Mass: 423.167332052
  • Average Mass: 423.894
DBSALT000326
Categories
UNII8L5014XET7
CAS number63590-64-7
WeightAverage: 387.4329
Monoisotopic: 387.190654313
Chemical FormulaC19H25N5O4
InChI KeyInChIKey=VCKUSRYTPJJLNI-UHFFFAOYSA-N
InChI
InChI=1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22)
IUPAC Name
6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine
SMILES
COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO1
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
  • Dialkylarylamine
  • Anisole
  • Aminopyrimidine
  • Alkyl aryl ether
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • Primary aromatic amine
  • Saccharide
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Oxolane
  • Tertiary amine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl 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 the treatment of symptomatic BPH and mild to moderate hypertension.
PharmacodynamicsTerazosin, classified as a quinazoline, is similar to doxazosin and prazosin. As an α-adrenergic blocking agent, terazosin is used to treat hypertension and BPH. Terazosin produces vasodilation and reduces peripheral resistance but in general has only a slight effect on cardiac output. The antihypertensive effect with chronic dosing is not usually accompanied by reflex tachycardia.
Mechanism of actionIn general, α1-adrenergic receptors mediate contraction and hypertrophic growth of smooth muscle cells. α1-Receptors are 7-transmembrane domain receptors coupled to G proteins, Gq/11. Three α1-receptor subtypes, which share approximately 75% homology in their transmembrane domains, have been identified: α1A (chromosome 8), α1B (chromosome 5), and α1D (chromosome 20). Terazosin is the first α1-receptor antagonist to demonstrate selectivity for the α1A-receptor. All three receptor subtypes appear to be involved in maintaining vascular tone. The α1A-receptor maintains basal vascular tone while the α1B-receptor mediates the vasocontrictory effects of exogenous α1-agonists. Activation of α1-receptors activates Gq-proteins, which results in intracellular stimulation of phospholipases C, A2, and D. This results in mobilization of Ca2+ from intracellular stores, activation of mitogen-activated kinase and PI3 kinase pathways and subsequent vasoconstriction. Terozosin produces its pharmacological effects by inhibiting α1A-receptor activation. Inhibition of these receptors in the vasculature and prostate results in muscle relaxation, decreased blood pressure and improved urinary outflow in symptomatic benign prostatic hyperplasia.
Related Articles
AbsorptionEssentially completely absorbed in man (90% bioavailability).
Volume of distributionNot Available
Protein binding90-94%
Metabolism

Hepatic. One of the four metabolites identified (piperazine derivative of terazosin) has antihypertensive activity.

Route of eliminationApproximately 10% of an orally administered dose is excreted as parent drug in the urine and approximately 20% is excreted in the feces.
Half life12 hours
ClearanceNot Available
ToxicityLD50=259.3mg/kg (IV in mice)
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+0.9646
Caco-2 permeable+0.8868
P-glycoprotein substrateSubstrate0.698
P-glycoprotein inhibitor INon-inhibitor0.5666
P-glycoprotein inhibitor IINon-inhibitor0.8619
Renal organic cation transporterNon-inhibitor0.6319
CYP450 2C9 substrateNon-substrate0.8864
CYP450 2D6 substrateNon-substrate0.8032
CYP450 3A4 substrateSubstrate0.7753
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9435
CYP450 2D6 inhibitorNon-inhibitor0.9628
CYP450 2C19 inhibitorNon-inhibitor0.9492
CYP450 3A4 inhibitorNon-inhibitor0.7905
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.901
Ames testNon AMES toxic0.5943
CarcinogenicityNon-carcinogens0.906
BiodegradationNot ready biodegradable0.9785
Rat acute toxicity2.2262 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8368
hERG inhibition (predictor II)Inhibitor0.8204
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Kit; tabletoral
Capsuleoral1 mg/1
Capsuleoral10 mg/1
Capsuleoral2 mg/1
Capsuleoral5 mg/1
Tabletoral1 mg
Tabletoral10 mg
Tabletoral2 mg
Tabletoral5 mg
Prices
Unit descriptionCostUnit
Hytrin 10 mg Tablet1.85USD tablet
Terazosin HCl 1 mg capsule1.67USD capsule
Terazosin HCl 10 mg capsule1.67USD capsule
Terazosin HCl 2 mg capsule1.67USD capsule
Terazosin HCl 5 mg capsule1.67USD capsule
Hytrin 5 mg Tablet1.26USD tablet
Hytrin 2 mg Tablet0.93USD tablet
Apo-Terazosin 10 mg Tablet0.92USD tablet
Novo-Terazosin 10 mg Tablet0.92USD tablet
Nu-Terazosin 10 mg Tablet0.92USD tablet
Pms-Terazosin 10 mg Tablet0.92USD tablet
Ratio-Terazosin 10 mg Tablet0.92USD tablet
Hytrin 1 mg Tablet0.73USD tablet
Apo-Terazosin 5 mg Tablet0.63USD tablet
Novo-Terazosin 5 mg Tablet0.63USD tablet
Nu-Terazosin 5 mg Tablet0.63USD tablet
Pms-Terazosin 5 mg Tablet0.63USD tablet
Ratio-Terazosin 5 mg Tablet0.63USD tablet
Apo-Terazosin 2 mg Tablet0.46USD tablet
Novo-Terazosin 2 mg Tablet0.46USD tablet
Nu-Terazosin 2 mg Tablet0.46USD tablet
Pms-Terazosin 2 mg Tablet0.46USD tablet
Ratio-Terazosin 2 mg Tablet0.46USD tablet
Apo-Terazosin 1 mg Tablet0.37USD tablet
Novo-Terazosin 1 mg Tablet0.37USD tablet
Nu-Terazosin 1 mg Tablet0.37USD tablet
Pms-Terazosin 1 mg Tablet0.37USD tablet
Ratio-Terazosin 1 mg Tablet0.37USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5212176 No1993-06-292010-06-29Us
US5294615 No1993-04-292013-04-29Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point273 °CPhysProp
water solubility29.7mg/mLNot Available
logP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.5 mg/mLALOGPS
logP1.12ALOGPS
logP1.18ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.93ChemAxon
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.04 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.18 m3·mol-1ChemAxon
Polarizability41.26 Å3ChemAxon
Number of Rings4ChemAxon
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 CodesG04CA03
AHFS Codes
  • 24:20.00
PDB EntriesNot Available
FDA labelDownload (1020 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Terazosin.
AlfuzosinAlfuzosin may increase the antihypertensive activities of Terazosin.
AmifostineTerazosin may increase the hypotensive activities of Amifostine.
AmlodipineTerazosin may increase the hypotensive activities of Amlodipine.
AmrinoneTerazosin may increase the hypotensive activities of Amrinone.
BepridilTerazosin may increase the hypotensive activities of Bepridil.
BrimonidineBrimonidine may increase the antihypertensive activities of Terazosin.
ButabarbitalButabarbital may increase the hypotensive activities of Terazosin.
ButethalButethal may increase the hypotensive activities of Terazosin.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Terazosin.
DiazoxideDiazoxide may increase the hypotensive activities of Terazosin.
DipivefrinTerazosin may decrease the vasoconstricting activities of Dipivefrin.
DuloxetineTerazosin may increase the orthostatic hypotensive activities of Duloxetine.
FelodipineTerazosin may increase the hypotensive activities of Felodipine.
FlunarizineTerazosin may increase the hypotensive activities of Flunarizine.
GabapentinTerazosin may increase the hypotensive activities of Gabapentin.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Terazosin.
HexobarbitalHexobarbital may increase the hypotensive activities of Terazosin.
IsradipineTerazosin may increase the hypotensive activities of Isradipine.
LamotrigineTerazosin may increase the hypotensive activities of Lamotrigine.
LercanidipineTerazosin may increase the hypotensive activities of Lercanidipine.
LevodopaTerazosin may increase the orthostatic hypotensive activities of Levodopa.
Magnesium SulfateTerazosin may increase the hypotensive activities of Magnesium Sulfate.
MethohexitalMethohexital may increase the hypotensive activities of Terazosin.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Terazosin.
MidodrineTerazosin may decrease the vasoconstricting activities of Midodrine.
MolsidomineMolsidomine may increase the hypotensive activities of Terazosin.
MoxonidineMoxonidine may increase the hypotensive activities of Terazosin.
NadololNadolol may increase the orthostatic hypotensive activities of Terazosin.
NicardipineTerazosin may increase the hypotensive activities of Nicardipine.
NicorandilNicorandil may increase the hypotensive activities of Terazosin.
NimodipineTerazosin may increase the hypotensive activities of Nimodipine.
NisoldipineTerazosin may increase the hypotensive activities of Nisoldipine.
NitrendipineTerazosin may increase the hypotensive activities of Nitrendipine.
ObinutuzumabTerazosin may increase the hypotensive activities of Obinutuzumab.
PentobarbitalPentobarbital may increase the hypotensive activities of Terazosin.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Terazosin.
PerhexilineTerazosin may increase the hypotensive activities of Perhexiline.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Terazosin.
PrazosinPrazosin may increase the antihypertensive activities of Terazosin.
PrenylamineTerazosin may increase the hypotensive activities of Prenylamine.
PrimidonePrimidone may increase the hypotensive activities of Terazosin.
QuinineQuinine may increase the hypotensive activities of Terazosin.
RisedronateTerazosin may increase the hypotensive activities of Risedronate.
RisperidoneTerazosin may increase the hypotensive activities of Risperidone.
RituximabTerazosin may increase the hypotensive activities of Rituximab.
SecobarbitalSecobarbital may increase the hypotensive activities of Terazosin.
TadalafilTadalafil may increase the hypotensive activities of Terazosin.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Terazosin.
TreprostinilTreprostinil may increase the hypotensive activities of Terazosin.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Terazosin.
VardenafilVardenafil may increase the hypotensive activities of Terazosin.
VerapamilTerazosin may increase the hypotensive activities of Verapamil.
YohimbineYohimbine may decrease the antihypertensive activities of Terazosin.
Food InteractionsNot Available

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. Chapple CR: Medical therapy and quality of life. Eur Urol. 1998;34 Suppl 2:10-7; discussion 46. [PubMed:9732824 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Lee E, Lee C: Clinical comparison of selective and non-selective alpha 1A-adrenoreceptor antagonists in benign prostatic hyperplasia: studies on tamsulosin in a fixed dose and terazosin in increasing doses. Br J Urol. 1997 Oct;80(4):606-11. [PubMed:9352700 ]
  4. 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 ]
  5. Na YJ, Guo YL, Gu FL: Clinical comparison of selective and non-selective alpha 1A-adrenoceptor antagonists for bladder outlet obstruction associated with benign prostatic hyperplasia: studies on tamsulosin and terazosin in Chinese patients. The Chinese Tamsulosin Study Group. J Med. 1998;29(5-6):289-304. [PubMed:10503165 ]
  6. 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 ]
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. Boyle P, Robertson C, Manski R, Padley RJ, Roehrborn CG: Meta-analysis of randomized trials of terazosin in the treatment of benign prostatic hyperplasia. Urology. 2001 Nov;58(5):717-22. [PubMed:11711348 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Simpson P: Stimulation of hypertrophy of cultured neonatal rat heart cells through an alpha 1-adrenergic receptor and induction of beating through an alpha 1- and beta 1-adrenergic receptor interaction. Evidence for independent regulation of growth and beating. Circ Res. 1985 Jun;56(6):884-94. [PubMed:2988814 ]
  4. Vincent J, Dachman W, Blaschke TF, Hoffman BB: Pharmacological tolerance to alpha 1-adrenergic receptor antagonism mediated by terazosin in humans. J Clin Invest. 1992 Nov;90(5):1763-8. [PubMed:1358918 ]
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. 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
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 ]

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, 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23