Identification

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

Prazosin, also known as Minipress, is a drug used to treat hypertension. Prazosin is marketed by Pfizer and was initially approved by the FDA in 1988 [16]. It belongs to the class of drugs known as alpha-1 antagonists [Label], [8].

Recently, many studies have evaluated the benefits of this drug in controlling the symptoms of post-traumatic stress disorder (PTSD) and associated nightmares [4, 5, 6].

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
  • Prazosin
  • Prazosina
  • Prazosine
  • Prazosinum
External IDs
CP-122991
Product Ingredients
IngredientUNIICASInChI Key
Prazosin hydrochlorideX0Z7454B9019237-84-4WFXFYZULCQKPIP-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MinipressCapsule1 mg/1OralPhysicians Total Care, Inc.1994-05-102012-06-30Us
MinipressCapsule2 mg/1OralPhysicians Total Care, Inc.1994-05-102012-06-30Us
MinipressTablet5 mgOralAspri Pharma Canada Inc1983-12-31Not applicableCanada
MinipressTablet1 mgOralAspri Pharma Canada Inc1983-12-31Not applicableCanada
MinipressTablet2 mgOralAspri Pharma Canada Inc1983-12-31Not applicableCanada
MinipressCapsule1 mg/1OralPfizer Laboratories Div Pfizer Inc.1994-05-10Not applicableUs
MinipressCapsule2 mg/1OralPfizer Laboratories Div Pfizer Inc.1994-05-10Not applicableUs
MinipressCapsule5 mg/1OralPfizer Laboratories Div Pfizer Inc.1994-05-10Not applicableUs
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 (2 mg/1) + Polythiazide (0.5 mg/1)CapsuleOralPfizer Labs2006-10-05Not applicableUs
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
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

This drug is indicated for the treatment of hypertension (high blood pressure). Prazosin can be given alone or given with other blood pressure-lowering drugs, including diuretics or beta-adrenergic blocking agents [Label].

Prazosin does not negatively impact lung function, and therefore may be used to manage hypertension in patients who are asthmatic or patients with chronic obstructive lung disease (COPD)[8].

Associated Conditions
Pharmacodynamics

Effects on blood pressure

The pharmacodynamic and therapeutic effect of this drug includes is a decrease in blood pressure as well as clinically significant decreases in cardiac output, heart rate, blood flow to the kidney, and glomerular filtration rate. The decrease in blood pressure may occur in both standing and supine positions [Label].

Many of the above effects are due to vasodilation of blood vessels caused by prazosin, resulting in decreased peripheral resistance [7], [Label]. Peripheral resistance refers to the level resistance of the blood vessels to blood that flows through them. As the blood vessels constrict (narrow), the resistance increases and as they dilate (widen), and peripheral resistance decreases, lowering blood pressure [14, 17].

Effects on sleep disturbance related to post-traumatic stress disorder (PTSD)

Some studies have suggested that this drug improves sleep in patients suffering from insomnia related to nightmares and post-traumatic stress disorder, caused by hyperarousal [5, 6]. This effect likely occurs through the inhibition of adrenergic stimulation found in states of hyperarousal [13].

Mechanism of action

Alpha-adrenergic receptors are essential for the regulation of blood pressure in humans. Two types of alpha receptors, alpha 1 and alpha 2, both play a role in regulating blood pressure. Alpha-1 receptors are postsynaptic (located after the nerve junction, or space between a nerve fiber and target tissue). In this case, the target tissue is the vascular smooth muscle [18]. These receptors, when activated, increase blood pressure [9].

Prazosin inhibits the postsynaptic alpha-1 adrenoceptors. This inhibition blocks the vasoconstricting (narrowing) effect of catecholamines (epinephrine and norepinephrine) on the vessels, leading to peripheral blood vessel dilation. Through blood vessel constriction by adrenergic receptor activation, epinephrine and norepinephrine normally act to increase blood pressure [10].

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Humans
AAlpha-1B adrenergic receptor
antagonist
Humans
AAlpha-1D adrenergic receptor
antagonist
Humans
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
UAlpha-2A adrenergic receptor
binder
Humans
UAlpha-2B adrenergic receptor
binder
Humans
UAlpha-1 adrenergic receptorsNot AvailableHumans
Absorption

After administration of an oral dose, peak plasma concentrations are attained at approximately 3 hours [Label]. There is a linear association between the prazosin dose given and plasma concentration at steady state [11].

Volume of distribution

About 0.6 L/kg [11].

Protein binding

Highly bound to proteins [Label] with 97% binding to albumin and alpha 1-acid glycoprotein [11]. Prazosin is thought to be mostly (about 80-90%) bound to albumin [15].

Metabolism

In animals, prazosin hydrochloride is heavily metabolized. This occurs through liver demethylation and conjugation [Label]. Some studies in humans or human cells in vitro show similar prazosin metabolism [7, 12].

Route of elimination

This drug is mainly excreted in the bile and the feces [Label].

Half life

The plasma half-life is about 2-3 hours [Label].

Clearance

In patients with congestive heart failure, the clearance of this drug is decreased. Impairment of renal function does not have relevant effects on elimination [8].

Toxicity

TDLO, LD50: Oral TDLO (human): 285 μg/kg; Oral TDLO (woman): 10 μg/kg [MSDS].

Oral LD50 (rat): 1950 mg/kg; Intraperitoneal LD50 (rat): 102 mg/kg [MSDS].

Overdose information

Accidental ingestion of at least 50 mg of prazosin by a two-year-old child led to severe drowsiness with depressed reflexes. There was no fall in blood pressure, and the child recovered without complication [Label].

Use in pregnancy

There are no adequate and well-controlled studies determining the safety of prazosin use during pregnancy. It is considered a pregnancy category C drug. Prazosin should be used during pregnancy only in cases where the benefit outweighs the possible risk to the mother and fetus [Label]. In specific cases where blood pressure control was emergent during pregnancy, prazosin has been used and no effects on the fetus or neonate were reported [Label].

Use in nursing

This drug is found excreted in small concentrations in human milk. This drug should be used with caution when used during nursing [Label].

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

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe therapeutic efficacy of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid can be increased when used in combination with Prazosin.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Prazosin.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Prazosin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Prazosin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Prazosin can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Prazosin.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Prazosin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of 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.
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. Kung S, Espinel Z, Lapid MI: Treatment of nightmares with prazosin: a systematic review. Mayo Clin Proc. 2012 Sep;87(9):890-900. doi: 10.1016/j.mayocp.2012.05.015. Epub 2012 Aug 9. [PubMed:22883741]
  5. Hudson SM, Whiteside TE, Lorenz RA, Wargo KA: Prazosin for the treatment of nightmares related to posttraumatic stress disorder: a review of the literature. Prim Care Companion CNS Disord. 2012;14(2). pii: 11r01222. doi: 10.4088/PCC.11r01222. Epub 2012 Mar 22. [PubMed:22943034]
  6. Koola MM, Varghese SP, Fawcett JA: High-dose prazosin for the treatment of post-traumatic stress disorder. Ther Adv Psychopharmacol. 2014 Feb;4(1):43-7. doi: 10.1177/2045125313500982. [PubMed:24490030]
  7. Jaillon P: Clinical pharmacokinetics of prazosin. Clin Pharmacokinet. 1980 Jul-Aug;5(4):365-76. doi: 10.2165/00003088-198005040-00004. [PubMed:6994981]
  8. Stanaszek WF, Kellerman D, Brogden RN, Romankiewicz JA: Prazosin update. A review of its pharmacological properties and therapeutic use in hypertension and congestive heart failure. Drugs. 1983 Apr;25(4):339-84. doi: 10.2165/00003495-198325040-00002. [PubMed:6303744]
  9. Reid JL: Alpha-adrenergic receptors and blood pressure control. Am J Cardiol. 1986 Mar 28;57(9):6E-12E. [PubMed:2869681]
  10. Lefevre-Borg F, Mathias O, Cavero I: Role of the sympathetic nervous system in blood pressure maintenance and in the antihypertensive effects of calcium antagonists in spontaneously hypertensive rats. Hypertension. 1988 Apr;11(4):360-70. [PubMed:2451639]
  11. Grahnen A, Seideman P, Lindstrom B, Haglund K, von Bahr C: Prazosin kinetics in hypertension. Clin Pharmacol Ther. 1981 Oct;30(4):439-46. [PubMed:7285477]
  12. Erve JC, Vashishtha SC, DeMaio W, Talaat RE: Metabolism of prazosin in rat, dog, and human liver microsomes and cryopreserved rat and human hepatocytes and characterization of metabolites by liquid chromatography/tandem mass spectrometry. Drug Metab Dispos. 2007 Jun;35(6):908-16. doi: 10.1124/dmd.106.013219. Epub 2007 Mar 12. [PubMed:17353349]
  13. Ronzoni G, Del Arco A, Mora F, Segovia G: Enhanced noradrenergic activity in the amygdala contributes to hyperarousal in an animal model of PTSD. Psychoneuroendocrinology. 2016 Aug;70:1-9. doi: 10.1016/j.psyneuen.2016.04.018. Epub 2016 Apr 25. [PubMed:27131036]
  14. Mayet J, Hughes A: Cardiac and vascular pathophysiology in hypertension. Heart. 2003 Sep;89(9):1104-9. [PubMed:12923045]
  15. Brunner F, Muller WE: Prazosin binding to human alpha 1-acid glycoprotein (orosomucoid), human serum albumin, and human serum. Further characterization of the 'single drug binding site' of orosomucoid. J Pharm Pharmacol. 1985 May;37(5):305-9. [PubMed:2862237]
  16. FDA approval information, Prazosin [Link]
  17. Cardiac anesthesiology, University of Toronto [Link]
  18. The pharmacology of adrenergic receptors [Link]
External Links
Human Metabolome Database
HMDB0014600
KEGG Drug
D08411
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
FDA label
Download (50.6 KB)
MSDS
Download (26.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAlcohol Use Disorders (AUD) / Smoking, Cigarette1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1RecruitingTreatmentAnxiety Disorders / Feeling Anxious1
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
2RecruitingTreatmentAlcohol Use Disorder (AUD) / Post Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentAlzheimer's Disease (AD) / Disruptive Behavior1
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 AvailableCompletedTreatmentBulimia Nervosa (BN) / Post Traumatic Stress Disorder (PTSD)1
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 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)277-280https://www.chemicalbook.com/ChemicalProductProperty_US_CB6120870.aspx
boiling point (°C)638.366http://www.chemspider.com/Chemical-Structure.4724.html
water solubility1.4 mg/mLhttps://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/1/p7791pis.pdf
logP1.3https://pubchem.ncbi.nlm.nih.gov/compound/prazosin
pKa6.54https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/1/p7791pis.pdf
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
Humans
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. 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]
  2. 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]
  3. 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]
  4. 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]
Kind
Protein
Organism
Humans
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. 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]
  2. 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]
  3. 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]
Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
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]
  2. Thomas D, Wu K, Wimmer AB, Zitron E, Hammerling BC, Kathofer S, Lueck S, Bloehs R, Kreye VA, Kiehn J, Katus HA, Schoels W, Karle CA: Activation of cardiac human ether-a-go-go related gene potassium currents is regulated by alpha(1A)-adrenoceptors. J Mol Med (Berl). 2004 Dec;82(12):826-37. doi: 10.1007/s00109-004-0582-8. Epub 2004 Sep 8. [PubMed:15365637]
Kind
Protein
Organism
Humans
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]
  2. Adams HR: Pharmacologic problems in circulation research: alpha adrenergic blocking drugs. Circ Shock. 1983;10(3):215-23. [PubMed:6133635]
  3. Bylund DB: Heterogeneity of alpha-2 adrenergic receptors. Pharmacol Biochem Behav. 1985 May;22(5):835-43. [PubMed:2989948]
Kind
Protein
Organism
Humans
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]
  2. Yasuda G, Sun L, Umemura S, Pettinger WA, Jeffries WB: Characterization of prazosin-sensitive alpha 2 B-adrenoceptors expressed by cultured rat IMCD cells. Am J Physiol. 1991 Nov;261(5 Pt 2):F760-6. doi: 10.1152/ajprenal.1991.261.5.F760. [PubMed:1719824]
  3. Bylund DB, Ray-Prenger C, Murphy TJ: Alpha-2A and alpha-2B adrenergic receptor subtypes: antagonist binding in tissues and cell lines containing only one subtype. J Pharmacol Exp Ther. 1988 May;245(2):600-7. [PubMed:2835476]
  4. Adams HR: Pharmacologic problems in circulation research: alpha adrenergic blocking drugs. Circ Shock. 1983;10(3):215-23. [PubMed:6133635]
  5. Bylund DB: Heterogeneity of alpha-2 adrenergic receptors. Pharmacol Biochem Behav. 1985 May;22(5):835-43. [PubMed:2989948]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
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...

Components:
References
  1. Prazosin FDA label [File]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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]
  2. Sager G, Jaeger R, Little C: Binding of prazosin to alpha 1-acid glycoprotein and albumin: effect of protein purity and concentrations. Pharmacol Toxicol. 1989 Apr;64(4):365-8. [PubMed:2748545]
  3. Brunner F, Muller WE: Prazosin binding to human alpha 1-acid glycoprotein (orosomucoid), human serum albumin, and human serum. Further characterization of the 'single drug binding site' of orosomucoid. J Pharm Pharmacol. 1985 May;37(5):305-9. [PubMed:2862237]
  4. Prazosin FDA label [File]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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]
  2. Sekhar GN, Georgian AR, Sanderson L, Vizcay-Barrena G, Brown RC, Muresan P, Fleck RA, Thomas SA: Organic cation transporter 1 (OCT1) is involved in pentamidine transport at the human and mouse blood-brain barrier (BBB). PLoS One. 2017 Mar 31;12(3):e0173474. doi: 10.1371/journal.pone.0173474. eCollection 2017. [PubMed:28362799]
  3. Dujic T, Zhou K, Donnelly LA, Tavendale R, Palmer CN, Pearson ER: Association of Organic Cation Transporter 1 With Intolerance to Metformin in Type 2 Diabetes: A GoDARTS Study. Diabetes. 2015 May;64(5):1786-93. doi: 10.2337/db14-1388. Epub 2014 Dec 15. [PubMed:25510240]
  4. 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
Humans
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
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Modulator
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. 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]
  2. 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]
  3. Lee CG, Gottesman MM, Cardarelli CO, Ramachandra M, Jeang KT, Ambudkar SV, Pastan I, Dey S: HIV-1 protease inhibitors are substrates for the MDR1 multidrug transporter. Biochemistry. 1998 Mar 17;37(11):3594-601. doi: 10.1021/bi972709x. [PubMed:9530286]
  4. Andrus MB, Mettath SN, Song C: A modified synthesis of iodoazidoaryl prazosin. J Org Chem. 2002 Nov 15;67(23):8284-6. [PubMed:12423172]
  5. Rautio J, Humphreys JE, Webster LO, Balakrishnan A, Keogh JP, Kunta JR, Serabjit-Singh CJ, Polli JW: In vitro p-glycoprotein inhibition assays for assessment of clinical drug interaction potential of new drug candidates: a recommendation for probe substrates. Drug Metab Dispos. 2006 May;34(5):786-92. doi: 10.1124/dmd.105.008615. Epub 2006 Feb 2. [PubMed:16455806]
Kind
Protein
Organism
Humans
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. Mukkavilli R, Jadhav G, Vangala S: Evaluation of Drug Transport in MDCKII-Wild Type, MDCKII-MDR1, MDCKII-BCRP and Caco-2 Cell Lines. Curr Pharm Biotechnol. 2017;18(14):1151-1158. doi: 10.2174/1389201019666180308091855. [PubMed:29521222]
  2. Wright JA, Haslam IS, Coleman T, Simmons NL: Breast cancer resistance protein BCRP (ABCG2)-mediated transepithelial nitrofurantoin secretion and its regulation in human intestinal epithelial (Caco-2) layers. Eur J Pharmacol. 2011 Dec 15;672(1-3):70-6. doi: 10.1016/j.ejphar.2011.10.004. Epub 2011 Oct 10. [PubMed:22004608]
  3. Giri N, Agarwal S, Shaik N, Pan G, Chen Y, Elmquist WF: Substrate-dependent breast cancer resistance protein (Bcrp1/Abcg2)-mediated interactions: consideration of multiple binding sites in in vitro assay design. Drug Metab Dispos. 2009 Mar;37(3):560-70. doi: 10.1124/dmd.108.022046. Epub 2008 Dec 4. [PubMed:19056916]
  4. Shemesh CS, Yu RZ, Warren MS, Liu M, Jahic M, Nichols B, Post N, Lin S, Norris DA, Hurh E, Huang J, Watanabe T, Henry SP, Wang Y: Assessment of the Drug Interaction Potential of Unconjugated and GalNAc3-Conjugated 2'-MOE-ASOs. Mol Ther Nucleic Acids. 2017 Dec 15;9:34-47. doi: 10.1016/j.omtn.2017.08.012. Epub 2017 Aug 30. [PubMed:29246313]

Drug created on June 13, 2005 07:24 / Updated on April 19, 2019 19:05