Identification

Name
Prazosin
Accession Number
DB00457  (APRD00020)
Type
Small Molecule
Groups
Approved
Description

Prazosin is a selective α-1-adrenergic receptor antagonist used to treat hypertension. It has also been used to decrease urinary obstruction and relieve symptoms associated with symptomatic benign prostatic hyperplasia. 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. Prazosin has also been used in conjunction with cardiac glycosides and diuretics in the management of severe congestive heart failure. It has also been used alone or in combination with β-blockers in the preoperative management of signs and symptoms of pheochromocytoma.

Structure
Thumb
Synonyms
  • 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine
  • 2-(4-(2-Furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline
  • Prazosina
  • Prazosine
  • Prazosinum
Product Ingredients
IngredientUNIICASInChI Key
Prazosin HydrochlorideX0Z7454B9019237-84-4WFXFYZULCQKPIP-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MinipressTablet5 mgOralAspri Pharma Canada Inc1983-12-31Not applicableCanada
MinipressCapsule1 mg/1OralPfizer Laboratories Div Pfizer Inc.1994-05-10Not applicableUs
MinipressTablet2 mgOralAspri Pharma Canada Inc1983-12-31Not applicableCanada
MinipressCapsule5 mg/1OralPfizer Laboratories Div Pfizer Inc.1994-05-10Not applicableUs
MinipressCapsule2 mg/1OralPhysicians Total Care, Inc.1994-05-102012-06-30Us
MinipressTablet1 mgOralAspri Pharma Canada Inc1983-12-31Not applicableCanada
MinipressCapsule2 mg/1OralPfizer Laboratories Div Pfizer Inc.1994-05-10Not applicableUs
MinipressCapsule1 mg/1OralPhysicians Total Care, Inc.1994-05-102012-06-30Us
Prazosin-1 Tab 1mgTablet1 mgOralPro Doc Limitee1991-12-312009-07-23Canada
Prazosin-2 Tab 2mgTablet2 mgOralPro Doc Limitee1991-12-312009-07-23Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-prazosin-tab 1mgTablet1 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Alti-prazosin-tab 2mgTablet2 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Alti-prazosin-tab 5mgTablet5 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Apo-prazo Tab 1mgTablet1 mgOralApotex Corporation1990-12-31Not applicableCanada
Apo-prazo Tab 2mgTablet2 mgOralApotex Corporation1990-12-31Not applicableCanada
Apo-prazo Tab 5mgTablet5 mgOralApotex Corporation1990-12-31Not applicableCanada
Nu-prazo Tab 1mgTablet1 mgOralNu Pharm Inc1992-12-312012-09-04Canada
Nu-prazo Tab 2mgTablet2 mgOralNu Pharm Inc1992-12-312012-09-04Canada
Nu-prazo Tab 5mgTablet5 mgOralNu Pharm Inc1992-12-312012-09-04Canada
PrazosinCapsule2 mg/1OralGreenstone, Llc2017-01-16Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MinizidePrazosin Hydrochloride (1 mg/1) + Polythiazide (0.5 mg/1)CapsuleOralPfizer Labs2006-10-05Not applicableUs
MinizidePrazosin Hydrochloride (5 mg/1) + Polythiazide (0.5 mg/1)CapsuleOralPfizer Labs2006-10-05Not applicableUs
MinizidePrazosin Hydrochloride (2 mg/1) + Polythiazide (0.5 mg/1)CapsuleOralPfizer Labs2006-10-05Not applicableUs
International/Other Brands
Hypovase / Minipress Xl (Pfizer) / Pressin / Vasoflex
Categories
UNII
XM03YJ541D
CAS number
19216-56-9
Weight
Average: 383.4011
Monoisotopic: 383.159354185
Chemical Formula
C19H21N5O4
InChI Key
IENZQIKPVFGBNW-UHFFFAOYSA-N
InChI
InChI=1S/C19H21N5O4/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/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)
IUPAC Name
2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine
SMILES
COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1

Pharmacology

Indication

For treatment of hypertension, symptomatic benign prostatic hyperplasia, and severe congestive heart failure. May also be used alone or in combination with β-blockers in the preoperative management of signs and symptoms of pheochromocytoma.

Associated Conditions
Pharmacodynamics

Prazosin is an alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Accordingly, Prazosin is a selective inhibitor of the alpha1 subtype of alpha adrenergic receptors. In the human prostate, Prazosin 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 Prazosin competitively antagonized the pressor effects of phenylephrine (an alpha1 agonist) and the systolic pressor effect of norepinephrine. The antihypertensive effect of Prazosin results from a decrease in systemic vascular resistance and the parent compound Prazosin is primarily responsible for the antihypertensive activity.

Mechanism of action

Prazosin 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.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Human
AAlpha-1B adrenergic receptor
antagonist
Human
AAlpha-1D adrenergic receptor
antagonist
Human
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Human
UPotassium voltage-gated channel subfamily H member 6
inhibitor
Human
UPotassium voltage-gated channel subfamily H member 7
inhibitor
Human
UAlpha-2A adrenergic receptor
binder
Human
UAlpha-2B adrenergic receptor
binder
Human
Absorption

Well-absorbed from gastrointestinal tract; bioavailability is variable (50 to 85%).

Volume of distribution
Not Available
Protein binding

97%

Metabolism

Primarily hepatic. Several metabolites have been identified in humans and animals (6- O -demethyl, 7- O -demethyl, 2-[1-piperazinyl]-4-amino-6, 7-dimethoxyquinazoline, 2,4-diamino-6,7-dimethoxyquinazoline).

Route of elimination

Animal studies indicate that prazosin hydrochloride is extensively metabolized, primarily by demethylation and conjugation, and excreted mainly via bile and feces. Less extensive human studies suggest similar metabolism and excretion in man.

Half life

2-3 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Prazosin.
AbediterolThe therapeutic efficacy of Abediterol can be decreased when used in combination with Prazosin.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Prazosin.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Prazosin.
AceclofenacThe therapeutic efficacy of Prazosin can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Prazosin can be decreased when used in combination with Acemetacin.
AcepromazinePrazosin may increase the orthostatic hypotensive, hypotensive, and antihypertensive activities of Acepromazine.
AcetaminophenThe serum concentration of Prazosin can be increased when it is combined with Acetaminophen.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Prazosin.
AdrafinilThe therapeutic efficacy of Adrafinil can be decreased when used in combination with Prazosin.
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Take without regard to meals.

References

Synthesis Reference

Stig O. E. Lindholm, "A process for the preparation of anhydrous, stable, crystalline delta-form of prazosin hydrochloride." U.S. Patent US4873330, issued 0000.

US4873330
General References
  1. Bawaskar HS, Bawaskar PH: Utility of scorpion antivenin vs prazosin in the management of severe Mesobuthus tamulus (Indian red scorpion) envenoming at rural setting. J Assoc Physicians India. 2007 Jan;55:14-21. [PubMed:17444339]
  2. 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]
  3. Hiraoka Y, Taniguchi T, Tanaka T, Okada K, Kanamaru H, Muramatsu I: Pharmacological characterization of unique prazosin-binding sites in human kidney. Naunyn Schmiedebergs Arch Pharmacol. 2003 Jul;368(1):49-56. Epub 2003 Jun 25. [PubMed:12827214]
  4. Link [Link]
External Links
Human Metabolome Database
HMDB0014600
KEGG Compound
C07368
PubChem Compound
4893
PubChem Substance
46508594
ChemSpider
4724
BindingDB
29568
ChEBI
8364
ChEMBL
CHEMBL2
Therapeutic Targets Database
DAP000300
PharmGKB
PA451093
IUPHAR
503
Guide to Pharmacology
GtP Drug Page
HET
XRA
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Prazosin
ATC Codes
C02LE01 — Prazosin and diureticsC02CA01 — Prazosin
AHFS Codes
  • 24:20.00 — Alpha-adrenergic Blocking Agents
PDB Entries
3owx
MSDS
Download (57.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAlcohol Use Disorders (AUD) / Smoking, Cigarette1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1WithdrawnOtherAcute Cardiovascular Disease / Cigarette Smoking Toxicity / Nicotine1
1, 2Active Not RecruitingTreatmentAlcohol Dependence1
1, 2CompletedScreeningAlcohol Dependence1
1, 2RecruitingTreatmentCombat Disorders / Headaches / Mild Traumatic Brain Injury (MTBI) / Post Concussion Syndrome / Posttraumatic Headache / Posttraumatic Migraine1
1, 2Unknown StatusTreatmentNeurogenic Bladder Dysfunction1
2CompletedHealth Services ResearchContinuous Methamphetamine Abuse1
2Not Yet RecruitingTreatmentAlzheimer's Disease (AD) / Disruptive Behavior1
2RecruitingTreatmentAlcohol Use Disorder (AUD) / Post Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentBlood Pressures / High Blood Pressure (Hypertension) / Stress, Psychological1
2TerminatedTreatmentNicotine Dependence1
2Unknown StatusTreatmentAlcohol Abuse / Posttraumatic Stress Disorders1
2Unknown StatusTreatmentAlcohol Dependence1
2Unknown StatusTreatmentChronic Hepatitis C Virus (HCV) Infection / Fibrosis1
3CompletedTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
3CompletedTreatmentPost Traumatic Stress Disorder (PTSD) / Sleep disorders and disturbances1
3CompletedTreatmentScorpion Envenomation1
3RecruitingTreatmentPosttraumatic Stress Disorders1
3Unknown StatusTreatmentRenal Stones1
4CompletedPreventionHemorrhage, Gastrointestinal / Liver Cirrhosis / Portal Hypertension1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentAllergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis1
4CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentNight-mares, Sleep disturbance / Post Traumatic Stress Disorder (PTSD) / Suicidal Thoughts1
4RecruitingOtherDementias1
4RecruitingTreatmentPost-Traumatic Headaches1
Not AvailableActive Not RecruitingTreatmentAlcohol Use Disorders (AUD) / Combat Disorders / Stress Disorders, Posttraumatic1
Not AvailableCompletedPreventionAutonomic Dysreflexia1
Not AvailableCompletedTreatmentAlcohol Use Disorder (AUD)1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD)1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD) / Psychomotor Agitation1
Not AvailableCompletedTreatmentAnxiety Disorders / Moods Disorders / Night-mares, Sleep disturbance / Sleeplessness1
Not AvailableCompletedTreatmentCombat Disorders / Post Traumatic Stress Disorder (PTSD) / Sleep disorders and disturbances1
Not AvailableCompletedTreatmentPost Traumatic Stress Disorder (PTSD) / Sleep disorders and disturbances1
Not AvailableCompletedTreatmentUrinary Retention1
Not AvailableRecruitingTreatmentAlcohol-Related Disorders / Brain Injury / Depression / Disease, Chronic / Mild Cognitive Impairment (MCI) / Pain NOS / Posttraumatic Stress Disorders / Quality of Life / Substance-Related Disorders / Suicidal Thoughts / Wounds and Injuries1
Not AvailableRecruitingTreatmentBulimia Nervosa (BN) / Post Traumatic Stress Disorder (PTSD)1
Not AvailableTerminatedTreatmentAlcohol Dependence / Dependence, Cocaine1
Not AvailableTerminatedTreatmentPost Traumatic Stress Disorder (PTSD)1
Not AvailableTerminatedTreatmentPost Traumatic Stress Disorder (PTSD) / Sleep Initiation and Maintenance Disorders1
Not AvailableTerminatedTreatmentPost Traumatic Stress Disorder (PTSD) / Sleep disorders and disturbances1
Not AvailableUnknown StatusTreatmentNon PTSD / Post Traumatic Stress Disorder (PTSD)1
Not AvailableUnknown StatusTreatmentPost Traumatic Stress Disorder (PTSD)1
Not AvailableWithdrawnBasic SciencePosttraumatic Stress Disorders1
Not AvailableWithdrawnBasic ScienceNo Condition, Basic Science1
Not AvailableWithdrawnTreatmentBipolar, Mania / Bipolar, Mixed State1

Pharmacoeconomics

Manufacturers
  • Pfizer laboratories div pfizer inc
  • American therapeutics inc
  • Clonmel healthcare ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Watson laboratories inc
  • Pfizer inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • A-S Medication Solutions LLC
  • BASF Corp.
  • Caremark LLC
  • Central Texas Community Health Centers
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Kramer-Novis
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
Dosage forms
FormRouteStrength
TabletOral1 mg
TabletOral2 mg
TabletOral5 mg
CapsuleOral
CapsuleOral1 mg/1
CapsuleOral2 mg/1
CapsuleOral5 mg/1
Prices
Unit descriptionCostUnit
Minipress 5 mg capsule1.97USD capsule
Minipress 2 mg capsule1.14USD capsule
Prazosin HCl 5 mg capsule0.98USD capsule
Prazosin 5 mg capsule0.94USD capsule
Minipress 1 mg capsule0.83USD capsule
Prazosin HCl 2 mg capsule0.57USD capsule
Prazosin 2 mg capsule0.55USD capsule
Prazosin HCl 1 mg capsule0.41USD capsule
Prazosin 1 mg capsule0.4USD capsule
Apo-Prazo 5 mg Tablet0.4USD tablet
Novo-Prazin 5 mg Tablet0.4USD tablet
Nu-Prazo 5 mg Tablet0.4USD tablet
Vasoflex hd caplet0.38USD caplet
Vasoflex forte capsule0.29USD capsule
Apo-Prazo 2 mg Tablet0.29USD tablet
Novo-Prazin 2 mg Tablet0.29USD tablet
Nu-Prazo 2 mg Tablet0.29USD tablet
Apo-Prazo 1 mg Tablet0.22USD tablet
Novo-Prazin 1 mg Tablet0.22USD tablet
Nu-Prazo 1 mg Tablet0.22USD tablet
Vasoflex tablet0.15USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)279 °CPhysProp
water solubility0.5 mg/mL (HCl salt)Sigma Aldrich
logP1.3Not Available
Caco2 permeability-4.36ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.693 mg/mLALOGPS
logP1.93ALOGPS
logP1.65ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.95 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.5 m3·mol-1ChemAxon
Polarizability40.49 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9479
Caco-2 permeable+0.8298
P-glycoprotein substrateSubstrate0.7193
P-glycoprotein inhibitor INon-inhibitor0.5747
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.6405
CYP450 2C9 substrateNon-substrate0.8773
CYP450 2D6 substrateNon-substrate0.7641
CYP450 3A4 substrateSubstrate0.7577
CYP450 1A2 substrateNon-inhibitor0.8434
CYP450 2C9 inhibitorNon-inhibitor0.9278
CYP450 2D6 inhibitorNon-inhibitor0.9685
CYP450 2C19 inhibitorNon-inhibitor0.9169
CYP450 3A4 inhibitorNon-inhibitor0.7608
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8049
Ames testNon AMES toxic0.5581
CarcinogenicityNon-carcinogens0.9199
BiodegradationNot ready biodegradable0.9818
Rat acute toxicity2.3304 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8352
hERG inhibition (predictor II)Inhibitor0.8489
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0019000000-9cca43997ddcbdd78e84
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0009000000-9da934e12af818eb0a08
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0009000000-85316e57dd3fefac386d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0019000000-09972bca73a43a1b73ab
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-1597000000-48d7b8ba991427bab5c2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-7491000000-4258e4db8045e56fe90f
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0002-0093000000-bffbfeafa12bdaf90f1d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0009000000-d13122c92100f1c0a02e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0009000000-b0b57af432244c705c26
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000t-1289000000-c6fe1f53648d640102aa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000t-3292000000-6907f1985350ad49c47b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000t-8490000000-f9e0f1ad0c30225b7de2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0009000000-77125e491b72f0b0adae
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0029000000-4492a1b0f9df7854cc06
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f8j-0392000000-b5c53dfdec441c727d1f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001r-0149000000-db377c2ba80a2269be91

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
N-arylpiperazines
Alternative Parents
Quinazolinamines / 2-heteroaryl carboxamides / Anisoles / Dialkylarylamines / Furoic acid and derivatives / Alkyl aryl ethers / Aminopyrimidines and derivatives / Imidolactams / Tertiary carboxylic acid amides / Heteroaromatic compounds
show 7 more
Substituents
N-arylpiperazine / Quinazolinamine / Diazanaphthalene / Quinazoline / 2-heteroaryl carboxamide / Furoic acid or derivatives / Anisole / Dialkylarylamine / Alkyl aryl ether / Aminopyrimidine
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, monocarboxylic acid amide, furans, quinazolines, piperazines (CHEBI:8364)

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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Chang HK, Hsu FL, Liu IM, Cheng JT: Stimulatory effect of cinnamic acid analogues on alpha1A-adrenoceptors in-vitro. J Pharm Pharmacol. 2003 Jun;55(6):833-7. [PubMed:12841945]
  2. Eltze M: In functional experiments, risperidone is selective, not for the B, but for the A subtype of alpha 1-adrenoceptors. Eur J Pharmacol. 1996 Jan 4;295(1):69-73. [PubMed:8925876]
  3. Morris DP, Price RR, Smith MP, Lei B, Schwinn DA: Cellular trafficking of human alpha1a-adrenergic receptors is continuous and primarily agonist-independent. Mol Pharmacol. 2004 Oct;66(4):843-54. Epub 2004 Jul 16. [PubMed:15258254]
  4. Sleight AJ, Koek W, Bigg DC: Binding of antipsychotic drugs at alpha 1A- and alpha 1B-adrenoceptors: risperidone is selective for the alpha 1B-adrenoceptors. Eur J Pharmacol. 1993 Jul 20;238(2-3):407-10. [PubMed:7691623]
  5. Suzuki Y, Kanada A, Okaya Y, Aisaka K: Effect of JTH-601, a novel alpha(1)-adrenoceptor antagonist, on prostate function in dogs. Eur J Pharmacol. 2000 Apr 7;394(1):123-30. [PubMed:10771044]
  6. Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [PubMed:17658513]
  7. Zacharia J, Hillier C, MacDonald A: Alpha1-adrenoceptor subtypes involved in vasoconstrictor responses to exogenous and neurally released noradrenaline in rat femoral resistance arteries. Br J Pharmacol. 2004 Mar;141(6):915-24. Epub 2004 Feb 23. [PubMed:14980979]
  8. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Al-Damluji S, Shen WB, White S, Barnard EA: alpha(1B) adrenergic receptors in gonadotrophin-releasing hormone neurones: relation to Transport-P. Br J Pharmacol. 2001 Jan;132(1):336-44. [PubMed:11156594]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  3. Eltze M: In functional experiments, risperidone is selective, not for the B, but for the A subtype of alpha 1-adrenoceptors. Eur J Pharmacol. 1996 Jan 4;295(1):69-73. [PubMed:8925876]
  4. Ishiguro M, Futabayashi Y, Ohnuki T, Ahmed M, Muramatsu I, Nagatomo T: Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. Life Sci. 2002 Oct 11;71(21):2531-41. [PubMed:12270758]
  5. Sharpe IA, Thomas L, Loughnan M, Motin L, Palant E, Croker DE, Alewood D, Chen S, Graham RM, Alewood PF, Adams DJ, Lewis RJ: Allosteric alpha 1-adrenoreceptor antagonism by the conopeptide rho-TIA. J Biol Chem. 2003 Sep 5;278(36):34451-7. Epub 2003 Jun 24. [PubMed:12824165]
  6. Sleight AJ, Koek W, Bigg DC: Binding of antipsychotic drugs at alpha 1A- and alpha 1B-adrenoceptors: risperidone is selective for the alpha 1B-adrenoceptors. Eur J Pharmacol. 1993 Jul 20;238(2-3):407-10. [PubMed:7691623]
  7. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
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
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Nagaoka Y, Ahmed M, Hossain M, Bhuiyan MA, Ishiguro M, Nakamura T, Watanabe M, Nagatomo T: Amino acids of the human alpha1d-adrenergic receptor involved in antagonist binding. J Pharmacol Sci. 2008 Jan;106(1):114-20. Epub 2008 Jan 11. [PubMed:18187928]
  2. Yamamoto Y, Koike K: alpha(1)-Adrenoceptor subtypes in the mouse mesenteric artery and abdominal aorta. Br J Pharmacol. 2001 Nov;134(5):1045-54. [PubMed:11682453]
  3. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
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 ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
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
Uniprot Name
Potassium voltage-gated channel subfamily H member 6
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
Uniprot Name
Potassium voltage-gated channel subfamily H member 7
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. [PubMed:1666366]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. [PubMed:1666366]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 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...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
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
Substrate
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607]
  2. Pan G, Winter TN, Roberts JC, Fairbanks CA, Elmquist WF: Organic cation uptake is enhanced in bcrp1-transfected MDCKII cells. Mol Pharm. 2010 Feb 1;7(1):138-45. doi: 10.1021/mp900177r. [PubMed:19886673]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674]
  2. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
  3. 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]
  4. Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956]
  5. Dey S, Ramachandra M, Pastan I, Gottesman MM, Ambudkar SV: Evidence for two nonidentical drug-interaction sites in the human P-glycoprotein. Proc Natl Acad Sci U S A. 1997 Sep 30;94(20):10594-9. [PubMed:9380680]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956]
  2. Ozvegy C, Litman T, Szakacs G, Nagy Z, Bates S, Varadi A, Sarkadi B: Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7. [PubMed:11437380]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 00:42