Doxazosin

Identification

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Name

Doxazosin

Accession Number

DB00590  (APRD00474)

Type

Small Molecule

Groups

Approved

Description

Doxazosin is an alpha-1 antagonist used for the treatment of benign prostatic hypertrophy (BPH) symptoms and hypertension. Other members of this drug class include Prazosin, Terazosin, Tamsulosin, and Alfuzosin.⁸ Because of its long-lasting effects, doxazosin can be administered once a day.⁵ It is marketed by Pfizer and was initially approved by the FDA in 1990.²⁰

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Doxazosin (DB00590)

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Synonyms

• 1-(4-Amino-6,7-dimethoxy-2-chinazolinyl)-4-(2,3-dihydro-1,4-benzodioxixin-2-ylcarbonyl)piperazin
• 1-(4-Amino-6,7-Dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazin
• Doxazosin
• Doxazosina
• Doxazosine
• Doxazosinum

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Doxazosin mesylate	86P6PQK0MU	77883-43-3	VJECBOKJABCYMF-UHFFFAOYSA-N

Product Images

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Cardura	Tablet	1 mg/1	Oral	Roerig	1990-11-02	Not applicable
Cardura	Tablet	8 mg/1	Oral	Physicians Total Care, Inc.	1994-12-13	2012-06-30
Cardura	Tablet	4 mg/1	Oral	Physicians Total Care, Inc.	1993-06-22	2012-07-16
Cardura	Tablet	8 mg/1	Oral	Roerig	1990-11-02	Not applicable
Cardura	Tablet	4 mg/1	Oral	Roerig	1990-11-02	Not applicable
Cardura	Tablet	2 mg/1	Oral	Physicians Total Care, Inc.	1999-02-10	2012-06-30
Cardura	Tablet	2 mg/1	Oral	Roerig	1990-11-02	Not applicable
Cardura	Tablet	1 mg/1	Oral	Physicians Total Care, Inc.	1995-10-16	2012-06-30
Cardura XL	Tablet, multilayer, extended release	8 mg/1	Oral	Roerig	2005-02-22	Not applicable
Cardura XL	Tablet, multilayer, extended release	4 mg/1	Oral	Roerig	2005-02-22	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Apo-doxazosin	Tablet		Oral	Apotex Corporation	1999-07-22	Not applicable
Apo-doxazosin	Tablet		Oral	Apotex Corporation	1999-07-22	Not applicable
Apo-doxazosin	Tablet		Oral	Apotex Corporation	1999-07-22	Not applicable
Dom-doxazosin	Tablet		Oral	Dominion Pharmacal	2004-05-26	Not applicable
Dom-doxazosin	Tablet		Oral	Dominion Pharmacal	2004-05-26	Not applicable
Dom-doxazosin	Tablet		Oral	Dominion Pharmacal	2004-05-26	Not applicable
Doxazosin	Tablet	4 mg/1	Oral	A-S Medication Solutions	2011-07-14	2019-01-31
Doxazosin	Tablet	4 mg/1	Oral	Major Pharmaceuticals	2011-07-14	Not applicable
Doxazosin	Tablet	8 mg/1	Oral	Ncs Health Care Of Ky, Inc Dba Vangard Labs	2000-10-19	Not applicable
Doxazosin	Tablet	4 mg/1	Oral	Remedy Repack	2013-03-27	2015-03-11

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Cardura-1,2,and 4	Doxazosin (1 mg) + Doxazosin (2 mg) + Doxazosin (4 mg)	Kit; Tablet	Oral	Astra Zeneca	Not applicable	Not applicable
Cardura-1,2,and 4	Doxazosin (1 mg) + Doxazosin (2 mg) + Doxazosin (4 mg)	Kit; Tablet	Oral	Astra Zeneca	Not applicable	Not applicable
Cardura-1,2,and 4	Doxazosin (1 mg) + Doxazosin (2 mg) + Doxazosin (4 mg)	Kit; Tablet	Oral	Astra Zeneca	Not applicable	Not applicable

International/Other Brands

Alfadil (Pfizer (Sweden)) / Cardenalin (Pfizer (Japan; discontinued)) / Cardular (Pfizer (Germany)) / Cardura-1 (Pfizer (Canada)) / Cardura-2 (Pfizer (Canada)) / Cardura-4 (Pfizer (Canada)) / Carduran (Pfizer (Brazil, Denmark, Norway, Spain)) / Diblocin (AstraZeneca (Germany)) / Normothen (Bioindustria (Italy)) / Supressin (Pfizer (Austria))

Categories

• Adrenergic Agents
• Adrenergic alpha-1 Receptor Antagonists
• Adrenergic alpha-Antagonists
• Adrenergic Antagonists
• Antiadrenergic Agents, Peripherally Acting
• Antihypertensive Agents
• Cardiovascular Agents
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Cytochrome P-450 Substrates
• Heterocyclic Compounds, Fused-Ring
• Hypotensive Agents
• Neurotransmitter Agents
• OCT1 inhibitors
• P-glycoprotein/ABCB1 Inhibitors
• Peripheral alpha-1 blockers
• Quinazolines

UNII

NW1291F1W8

CAS number

74191-85-8

Weight

Average: 451.4751
Monoisotopic: 451.185568935

Chemical Formula

C₂₃H₂₅N₅O₅

InChI Key

RUZYUOTYCVRMRZ-UHFFFAOYSA-N

InChI

InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)

IUPAC Name

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

SMILES

COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1COC2=CC=CC=C2O1

Pharmacology

Indication

Doxazosin is indicated to treat the symptoms of benign prostatic hypertrophy, which may include urinary frequency, urgency, and nocturia, among other symptoms. In addition, doxazosin is indicated alone or in combination with various antihypertensive agents for the management of hypertension.¹⁹ Off-label uses of doxazosin include the treatment of pediatric hypertension² and the treatment of ureteric calculi.³

Associated Conditions

• Benign Prostatic Hypertrophy (BPH)
• High Blood Pressure (Hypertension)
• Ureteric calculus

Pharmacodynamics

Doxazosin decreases standing and supine blood pressure⁵ and relieves the symptoms of benign prostatic hypertrophy through the inhibition of alpha-1 receptors. Doxazosin may cause hypotension due to its pharmacological actions. This frequently occurs in the upright position, leading to a feeling of dizziness or lightheadedness. The first dose of doxazosin may lead to such effects, however, subsequent doses may also cause them. The risk of these effects is particularly high when dose adjustments occur or there are long intervals between doxazosin doses. Treatment should be started with the 1 mg dose of doxazosin, followed by slow titration to the appropriate dose.¹⁹ Patients must be advised of this risk and to avoid situations in which syncope and dizziness could be hazardous following the ingestion of doxazosin.¹⁹ Interestingly doxazosin exerts beneficial effects on plasma lipids. It reduces LDL (low-density lipoprotein) cholesterol and triglyceride levels and increases HDL (high-density lipoprotein) cholesterol levels.⁵

A note on priapism risk

In rare cases, doxazosin and other alpha-1 blockers may cause priapism, a painful occurrence of persistent and unrelievable penile erection that can lead to impotence if medical attention is not sought as soon as possible. Patients must be advised of the priapism risk associated with doxazosin and to seek medical attention immediately if it is suspected.^9,19

Mechanism of action

Doxazosin selectively inhibits the postsynaptic alpha-1 receptors on vascular smooth muscle by nonselectively blocking the alpha-1a, alpha-1b, and alpha-1d subtypes^12,13. This action on blood vessels decreases systemic peripheral vascular resistance, reducing blood pressure, exerting minimal effects on the heart rate due to its receptor selectivity.^5,10 Norepinephrine-activated alpha-1 receptors located on the prostate gland and bladder neck normally cause contraction of regional muscular tissue, obstructing urinary flow and contributing to the symptoms of benign prostatic hypertrophy. Alpha-1 antagonism causes smooth muscle relaxation in the prostate and bladder, effectively relieving urinary frequency, urgency, weak urinary stream, and other unpleasant effects of BPH.⁶ Recently, doxazosin was found to cause apoptosis of hERG potassium channels in an in vitro setting, possibly contributing to a risk of heart failure with doxazosin use.^14,15,16

Target	Actions	Organism
AAlpha-1A adrenergic receptor	antagonist	Humans
AAlpha-1D adrenergic receptor	antagonist	Humans
UHERG human cardiac K+ channel	inhibitor	Humans
UAlpha-1B adrenergic receptor	Not Available	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

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Absorption

Doxazosin is rapidly absorbed in the gastrointestinal tract and peak concentrations are achieved within 2-3 hours after administration.¹¹ The bioavailability is about 60%-70%.^7,19 The intake of food with doxazosin is not expected to cause clinically significant effects.¹⁹

Volume of distribution

The volume of distribution of doxazosin is 1.0-1.9 L/kg.^7,11 In a study of radiolabeled doxazosin administered to pregnant rats, doxazosin was found to cross the placenta.¹⁹

Protein binding

The plasma protein binding of doxazosin is estimated at 98%.^4,19. It has also been shown to be bound to the alpha-1 acid glycoprotein.¹⁸

Metabolism

Hepatic metabolism of doxazosin produces inactive O-demethylated and C-hydroxylated metabolites. Metabolism occurs via O-demethylation of the quinazoline nucleus of doxazosin or via hydroxylation of its benzodioxan portion.¹⁹ The enzymes involved in the metabolism of doxazosin include CYP2C19²³, CYP2D6, CYP2C19, and CYP3A4, which is the primary metabolizing enzyme.²² Doxazosin itself is considered to be mainly responsible for its pharmacological action⁷, however, some active metabolites have been identified whose pharmacokinetics have not been adequately characterized.¹⁹

• Doxazosin
  Demethylated metabolite, Doxazosin
• Doxazosin
  Hydroxylated metabolite, Doxazosin

Route of elimination

In a pharmacokinetic study using a 1 mg IV radiolabeled dose and a 2 mg oral dose, 63% of the ingested doxazosin was found to be excreted in the feces and about 9% of the dose was found to be excreted in the urine.^7,19 Traces of radiolabeled unchanged drug were found in the urine and about 5% of the administered drug was found as unchanged drug excreted in the feces.¹⁹

Half life

The terminal elimination half-life of doxazosin has been estimated at 9-12 hours according to some resources.^4,7 The FDA label indicates the elimination half-life of doxazosin is 22 hours.¹⁹

Clearance

The clearance of doxazosin is low and ranges from approximately 1-2 ml/min/kg.^4,11

Toxicity

LD50 information

The oral LD50 of doxazosin in mice is >1000 mg/kg.²¹

Overdose information

Symptoms of overdose include hypotension, changes in heart rate, and drowsiness.¹⁰ Administer supportive treatment in case of an overdose with doxazosin. Remove unabsorbed doxazosin from the gastrointestinal tract, correct hypotension, and closely monitor vital signs.¹⁰

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Doxazosin.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Doxazosin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine	The metabolism of Doxazosin can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Doxazosin.
1-benzylimidazole	1-benzylimidazole may decrease the antihypertensive activities of Doxazosin.
2,5-Dimethoxy-4-ethylamphetamine	The therapeutic efficacy of Doxazosin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The therapeutic efficacy of Doxazosin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Doxazosin.
4-Bromo-2,5-dimethoxyamphetamine	The therapeutic efficacy of Doxazosin can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamine	The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Doxazosin.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Evidence Level
Evidence Level
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Action
Action
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Food Interactions

• Avoid alcohol.
• Avoid natural licorice.
• Take without regard to meals.

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]
2. Rao G: Diagnosis, Epidemiology, and Management of Hypertension in Children. Pediatrics. 2016 Aug;138(2). pii: peds.2015-3616. doi: 10.1542/peds.2015-3616. Epub 2016 Jul 12. [PubMed:27405770]
3. Liatsikos EN, Katsakiori PF, Assimakopoulos K, Voudoukis T, Kallidonis P, Constantinides C, Athanasopoulos A, Stolzenburg JU, Perimenis P: Doxazosin for the management of distal-ureteral stones. J Endourol. 2007 May;21(5):538-41. doi: 10.1089/end.2006.0107. [PubMed:17523910]
4. Kaye B, Cussans NJ, Faulkner JK, Stopher DA, Reid JL: The metabolism and kinetics of doxazosin in man, mouse, rat and dog. Br J Clin Pharmacol. 1986;21 Suppl 1:19S-25S. doi: 10.1111/j.1365-2125.1986.tb02849.x. [PubMed:2939865]
5. Young RA, Brogden RN: Doxazosin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in mild or moderate hypertension. Drugs. 1988 May;35(5):525-41. doi: 10.2165/00003495-198835050-00003. [PubMed:2899495]
6. Doggrell SA: After ALLHAT: doxazosin for the treatment of benign prostatic hyperplasia. Expert Opin Pharmacother. 2004 Sep;5(9):1957-64. doi: 10.1517/14656566.5.9.1957 . [PubMed:15330733]
7. Elliott HL, Meredith PA, Reid JL: Pharmacokinetic overview of doxazosin. Am J Cardiol. 1987 May 29;59(14):78G-81G. doi: 10.1016/0002-9149(87)90162-7. [PubMed:2884857]
8. Kaplan SA: alpha-Blocker Therapy: Current Update. Rev Urol. 2005;7 Suppl 8:S34-42. [PubMed:16985889]
9. Pahuja A, Bashir J, Williamson EM, Barber N: Unresolved priapism secondary to tamsulosin. Int J Impot Res. 2005 May-Jun;17(3):293-4. doi: 10.1038/sj.ijir.3901281. [PubMed:15549140]
10. Satar S, Sebe A, Avci A, Yesilagac H, Gokel Y: Acute intoxication with doxazosin. Hum Exp Toxicol. 2005 Jun;24(6):337-9. doi: 10.1191/0960327105ht531oa. [PubMed:16004202]
11. Cubeddu LX, Fuenmayor N, Caplan N, Ferry D: Clinical pharmacology of doxazosin in patients with essential hypertension. Clin Pharmacol Ther. 1987 Apr;41(4):439-49. doi: 10.1038/clpt.1987.54. [PubMed:2951051]
12. Schwinn DA, Roehrborn CG: Alpha1-adrenoceptor subtypes and lower urinary tract symptoms. Int J Urol. 2008 Mar;15(3):193-9. doi: 10.1111/j.1442-2042.2007.01956.x. [PubMed:18304211]
13. Martin DJ, Lluel P, Guillot E, Coste A, Jammes D, Angel I: Comparative alpha-1 adrenoceptor subtype selectivity and functional uroselectivity of alpha-1 adrenoceptor antagonists. J Pharmacol Exp Ther. 1997 Jul;282(1):228-35. [PubMed:9223558]
14. 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]
15. Thomas D, Bloehs R, Koschny R, Ficker E, Sykora J, Kiehn J, Schlomer K, Gierten J, Kathofer S, Zitron E, Scholz EP, Kiesecker C, Katus HA, Karle CA: Doxazosin induces apoptosis of cells expressing hERG K+ channels. Eur J Pharmacol. 2008 Jan 28;579(1-3):98-103. doi: 10.1016/j.ejphar.2007.10.051. Epub 2007 Dec 4. [PubMed:18054910]
16. Jehle J, Schweizer PA, Katus HA, Thomas D: Novel roles for hERG K(+) channels in cell proliferation and apoptosis. Cell Death Dis. 2011 Aug 18;2:e193. doi: 10.1038/cddis.2011.77. [PubMed:21850047]
17. Hammond KP, Nielsen C, Linnebur SA, Langness JA, Ray G, Maroni P, Kiser JJ: Priapism induced by boceprevir-CYP3A4 inhibition and alpha-adrenergic blockade: case report. Clin Infect Dis. 2014 Jan;58(1):e35-8. doi: 10.1093/cid/cit673. Epub 2013 Oct 2. [PubMed:24092799]
18. 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. doi: 10.1002/jps.2600750208. [PubMed:2870173]
19. Doxazosin FDA label [Link]
20. FDA approval package, Cardura [Link]
21. MSDS, Pfizer [Link]
22. Cardura XL label [Link]
23. Cardura monograph [Link]

External Links

Human Metabolome Database

HMDB0014728

KEGG Drug

D07874

KEGG Compound

C06970

PubChem Compound

3157

PubChem Substance

46506825

ChemSpider

3045

BindingDB

86731

ChEBI

4708

ChEMBL

CHEMBL707

Therapeutic Targets Database

DAP000381

PharmGKB

PA449407

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Doxazosin

ATC Codes

C02CA04 — Doxazosin

• C02CA — Alpha-adrenoreceptor antagonists
• C02C — ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING
• C02 — ANTIHYPERTENSIVES
• C — CARDIOVASCULAR SYSTEM

AHFS Codes

• 24:20.00 — Alpha-adrenergic Blocking Agents

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Cocaine Abuse / Dependence, Cocaine / Substance Abuse	1
1	Completed	Not Available	Substance-Related Disorders	1
1	Completed	Basic Science	Amphetamine-Related Disorders / Moods Disorders / Substance-Related Disorders	1
1	Completed	Treatment	Dependence, Cocaine	1
1	Completed	Treatment	Erectile Dysfunction (ED)	1
1	Completed	Treatment	Healthy Volunteers	1
1	Completed	Treatment	High Blood Pressure (Hypertension)	1
1	Not Yet Recruiting	Other	Alcohol Use Disorder (AUD)	1
1	Recruiting	Treatment	Allogeneic Hematopoietic Stem Cell Transplant Recipient / Allogeneic Hematopoietic Stem Cell Transplantation Recipient / Blasts Under 5 Percent of Bone Marrow Nucleated Cells / IDH2 Gene Mutation / Leukemia Acute Myeloid Leukemia (AML) / Myeloid leukaemia in remission	1
1	Recruiting	Treatment	Dependence, Cocaine	1
1	Recruiting	Treatment	Post Traumatic Stress Disorder (PTSD)	1
1, 2	Active Not Recruiting	Treatment	Alcohol Use Disorder (AUD) / Post Traumatic Stress Disorder (PTSD)	1
1, 2	Completed	Treatment	Methamphetamine or Cocaine Dependence	1
2	Active Not Recruiting	Treatment	Alcohol Use Disorders (AUD) / Post Traumatic Stress Disorder (PTSD) / Posttraumatic Stress Disorders	1
2	Completed	Diagnostic	Dependence, Cocaine	1
2	Completed	Treatment	Alcohol Dependence / Anxiety	1
2	Completed	Treatment	Benign Prostatic Hyperplasia (BPH)	1
2	Completed	Treatment	Cardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases	1
2	Completed	Treatment	Dependence, Cocaine	1
2	Completed	Treatment	Smoking	1
2	Not Yet Recruiting	Treatment	Acute, recurrent Myeloid Leukemia / Blasts 5 Percent or More of Bone Marrow Nucleated Cells / IDH2 Gene Mutation	1
2	Recruiting	Treatment	Acute Bilineal Leukemia / Acute Biphenotypic Leukemia (ABL) / Acute, recurrent Myeloid Leukemia / Chronic Myelomonocytic Leukemia / IDH2 Gene Mutation / Myelodysplastic Syndrome / Refractory Acute Myeloid Leukemia	1
2	Recruiting	Treatment	Alcohol Dependence	1
2	Recruiting	Treatment	Post Traumatic Stress Disorder (PTSD)	1
2, 3	Recruiting	Treatment	High Blood Pressure (Hypertension)	1
3	Completed	Prevention	Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / Heart Failure / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Infarction / Myocardial Ischemia	1
3	Completed	Treatment	Prostatic Hyperplasia / Prostatic Hypertrophy, Benign	1
3	Recruiting	Treatment	Paraganglioma / Pheochromocytomas	1
3	Unknown Status	Treatment	Renal Stones	1
4	Active Not Recruiting	Treatment	Hypertension, Resistant to Conventional Therapy	1
4	Completed	Basic Science	Idiopathic Dilated Cardiomyopathy	1
4	Completed	Treatment	Allergic Rhinitis (AR)	1
4	Completed	Treatment	Bladder Outlet Obstruction	1
4	Completed	Treatment	Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension,Essential / Strokes	1
4	Completed	Treatment	Diabetes Mellitus (DM) / Hypertension,Essential / Renal Failure	1
4	Completed	Treatment	High Blood Pressure (Hypertension)	6
4	Completed	Treatment	Pheochromocytomas	1
4	Completed	Treatment	Post Traumatic Stress Disorder (PTSD)	1
4	Completed	Treatment	Prostate	1
4	Unknown Status	Prevention	Diabetic Nephropathies	1
4	Unknown Status	Treatment	Benign Prostatic Hyperplasia (BPH) / Urinary Bladder, Overactive	1
4	Withdrawn	Treatment	Benign Prostatic Hyperplasia (BPH)	1
Not Available	Completed	Not Available	Benign Prostatic Hyperplasia (BPH)	1
Not Available	Completed	Not Available	Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Infarction	1
Not Available	Completed	Not Available	Prostatic Hyperplasia	3
Not Available	Completed	Basic Science	Benign Prostatic Hyperplasia (BPH)	1
Not Available	Terminated	Treatment	High Blood Pressure (Hypertension)	1
Not Available	Terminated	Treatment	High Blood Pressure (Hypertension) / Microvascular Angina	1
Not Available	Terminated	Treatment	Prostatic Hyperplasia / Urinary Retention	1

Pharmacoeconomics

Manufacturers

• Pfizer inc
• Pfizer laboratories div pfizer inc
• Actavis elizabeth llc
• Apotex inc
• Dava pharmaceuticals inc
• Genpharm inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Kv pharmaceutical co
• Mylan pharmaceuticals inc
• Pliva inc
• Sandoz inc
• Teva pharmaceuticals usa inc
• Watson laboratories inc

Packagers

• Actavis Group
• Advanced Pharmaceutical Services Inc.
• Amerisource Health Services Corp.
• Apotex Inc.
• A-S Medication Solutions LLC
• Cardinal Health
• DAVA Pharmaceuticals
• Dept Health Central Pharmacy
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• General Injectables and Vaccines Inc.
• Golden State Medical Supply Inc.
• Heartland Repack Services LLC
• International Laboratories Inc.
• Ivax Pharmaceuticals
• Legacy Pharmaceuticals Packaging LLC
• Major Pharmaceuticals
• Merrell Pharmaceuticals Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Novopharm Ltd.
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Par Pharmaceuticals
• Patheon Inc.
• Pfizer Inc.
• Pharmaceutical Utilization Management Program VA Inc.
• Physicians Total Care Inc.
• Pliva Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Redpharm Drug
• Remedy Repack
• Sandhills Packaging Inc.
• Southwood Pharmaceuticals
• Stat Rx Usa
• Teva Pharmaceutical Industries Ltd.
• Torpharm Inc.
• Tya Pharmaceuticals
• UDL Laboratories
• US Pharmaceutical Group
• Vangard Labs Inc.

Dosage forms

Form	Route	Strength
Tablet, multilayer, extended release	Oral	4 mg/1
Tablet, multilayer, extended release	Oral	8 mg/1
Tablet	Oral
Kit; tablet	Oral
Tablet	Oral	1 mg/1
Tablet	Oral	2 mg/1
Tablet	Oral	4 mg/1
Tablet	Oral	8 mg/1

Prices

Unit description	Cost	Unit
Cardura XL 4 mg 24 Hour tablet	2.22USD	tablet
Cardura xl 8 mg tablet	2.04USD	tablet
Cardura xl 4 mg tablet	1.94USD	tablet
Cardura 8 mg tablet	1.93USD	tablet
Cardura 4 mg tablet	1.89USD	tablet
Cardura 2 mg tablet	1.81USD	tablet
Cardura 1 mg tablet	1.72USD	tablet
Doxazosin mesylate 8 mg tablet	1.04USD	tablet
Cardura 4 mg Tablet	1.0USD	tablet
Doxazosin mesylate 4 mg tablet	0.99USD	tablet
Doxazosin mesylate 1 mg tablet	0.94USD	tablet
Doxazosin mesylate 2 mg tablet	0.94USD	tablet
Cardura 2 mg Tablet	0.77USD	tablet
Cardura 1 mg Tablet	0.64USD	tablet
Apo-Doxazosin 4 mg Tablet	0.56USD	tablet
Mylan-Doxazosin 4 mg Tablet	0.56USD	tablet
Novo-Doxazosin 4 mg Tablet	0.56USD	tablet
Pms-Doxazosin 4 mg Tablet	0.56USD	tablet
Apo-Doxazosin 2 mg Tablet	0.43USD	tablet
Mylan-Doxazosin 2 mg Tablet	0.43USD	tablet
Novo-Doxazosin 2 mg Tablet	0.43USD	tablet
Pms-Doxazosin 2 mg Tablet	0.43USD	tablet
Apo-Doxazosin 1 mg Tablet	0.36USD	tablet
Mylan-Doxazosin 1 mg Tablet	0.36USD	tablet
Novo-Doxazosin 1 mg Tablet	0.36USD	tablet
Pms-Doxazosin 1 mg Tablet	0.36USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	275-277	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3285710.htm
boiling point (°C)	718	https://www.scbt.com/scbt/product/doxazosin-mesylate-77883-43-3
water solubility	0.8%	https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019668s021lbl.pdf
logP	2.1	https://pubchem.ncbi.nlm.nih.gov/compound/Doxazosin
pKa	6.52	https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL707/

Predicted Properties

Property	Value	Source
Water Solubility	0.79 mg/mL	ALOGPS
logP	2.53	ALOGPS
logP	2.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.67	ChemAxon
pKa (Strongest Basic)	7.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å2	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.64 m3·mol-1	ChemAxon
Polarizability	47.17 Å3	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9627
Caco-2 permeable	+	0.7863
P-glycoprotein substrate	Substrate	0.7303
P-glycoprotein inhibitor I	Non-inhibitor	0.7391
P-glycoprotein inhibitor II	Non-inhibitor	0.9528
Renal organic cation transporter	Non-inhibitor	0.6909
CYP450 2C9 substrate	Non-substrate	0.9011
CYP450 2D6 substrate	Non-substrate	0.8195
CYP450 3A4 substrate	Substrate	0.7228
CYP450 1A2 substrate	Non-inhibitor	0.8293
CYP450 2C9 inhibitor	Non-inhibitor	0.9161
CYP450 2D6 inhibitor	Non-inhibitor	0.9533
CYP450 2C19 inhibitor	Non-inhibitor	0.9084
CYP450 3A4 inhibitor	Non-inhibitor	0.8002
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9078
Ames test	Non AMES toxic	0.5648
Carcinogenicity	Non-carcinogens	0.8905
Biodegradation	Not ready biodegradable	0.9854
Rat acute toxicity	2.1954 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8602
hERG inhibition (predictor II)	Inhibitor	0.823

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udi-0010900000-9601aa919c95799ec009
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0kei-0981100000-a9ee3121ba6832366f8e
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0a4i-0970000000-5261f1bc60ceee4364de
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0a4i-0950000000-f649236044e4e2a5de38
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0a4i-1920000000-86655cc3bb892d757068
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0a4i-1900000000-88bca2ddf2930fa0c468
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-0000900000-449254642300c1324285
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-0002900000-3097c8a3403b52610918
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0006-0079100000-06d36a9b7afe6cf0c6e9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000t-1091000000-cbd9b2106818ef5fd2ba
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-001i-1190000000-a1c84b0c3657d8000e35
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-001i-1390000000-e802cb93ca8d6934ee96

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 / Benzo-1,4-dioxanes / Anisoles / Dialkylarylamines / Alkyl aryl ethers / Aminopyrimidines and derivatives / Para dioxins / Imidolactams / Tertiary carboxylic acid amides / Heteroaromatic compoundsAmino acids and derivatives / Oxacyclic compounds / Azacyclic compounds / Primary amines / Organic oxides / Organopnictogen compounds / Hydrocarbon derivatives / Carbonyl compounds

show 8 more

Substituents

N-arylpiperazine / Quinazolinamine / Diazanaphthalene / Benzo-1,4-dioxane / Benzodioxane / Quinazoline / Anisole / Dialkylarylamine / Alkyl aryl ether / AminopyrimidinePara-dioxin / Pyrimidine / Imidolactam / Benzenoid / Heteroaromatic compound / Tertiary carboxylic acid amide / Carboxamide group / Amino acid or derivatives / Oxacycle / Azacycle / Carboxylic acid derivative / Ether / Organic oxygen compound / Amine / Carbonyl group / Organic nitrogen compound / Hydrocarbon derivative / Organic oxide / Organopnictogen compound / Organonitrogen compound / Organooxygen compound / Primary amine / Aromatic heteropolycyclic compound

show 23 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine, monocarboxylic acid amide, aromatic amine, quinazolines, benzodioxine, N-acylpiperazine (CHEBI:4708)

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Drug created on June 13, 2005 07:24 / Updated on October 21, 2019 05:03