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Details

Stereochemistry RACEMIC
Molecular Formula C19H27N5O4
Molecular Weight 389.4495
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFUZOSIN

SMILES

CN(CCCN=C(C1CCCO1)O)c2nc3cc(c(cc3c(=N)[nH]2)OC)OC

InChI

InChIKey=WNMJYKCGWZFFKR-UHFFFAOYSA-N
InChI=1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23)

HIDE SMILES / InChI
signs and symptoms of benign prostatic hyperplasia. UROXATRAL is not indicated for the treatment of hypertension. Alfuzosin is a non-subtype specific alpha(1)-adrenergic blocking agent that exhibits selectivity for alpha(1)-adrenergic receptors in the lower urinary tract. Inhibition of these adrenoreceptors leads to the relaxation of smooth muscle in the bladder neck and prostate, resulting in the improvement in urine flow and a reduction in symptoms in benign prostate hyperplasia. Alfuzosin also inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation.

CNS Activity

Curator's Comment:: Alfuzosin does not penetrate the blood–brain barrier well

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
UROXATRAL

Approved Use

UROXATRAL is indicated for the treatment of signs and symptoms of benign prostatic hyperplasia. UROXATRAL is an alpha adrenergic antagonist, indicated for the treatment of signs and symptoms of benign prostatic hyperplasia. (1) Important Limitations of Use: UROXATRAL is not indicated for treatment of hypertension. (1.1) UROXATRAL is not indicated for use in the pediatric population. (1.1, 8.4, 12.3) 1.1 Important Limitations of Use UROXATRAL is not indicated for the treatment of hypertension. UROXATRAL is not indicated for use in the pediatric population.

Launch Date

1055376000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.6 ng/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALFUZOSIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
194 ng × h/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALFUZOSIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALFUZOSIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
14%
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALFUZOSIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day single, oral
Highest studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, mean age 27 years
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Sources:
Other AEs: Dizziness, Headache...
Other AEs:
Dizziness (8.9%)
Headache (6.7%)
Malaise (2%)
Sources:
4.4 mg 2 times / day multiple, oral
Recommended
Dose: 4.4 mg, 2 times / day
Route: oral
Route: multiple
Dose: 4.4 mg, 2 times / day
Sources:
unhealthy, mean age 62.6 years
Health Status: unhealthy
Age Group: mean age 62.6 years
Sex: M
Sources:
Disc. AE: Abdominal pain, Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (grade 1-2, 1.1%)
Diarrhoea (grade 1-2, 1.1%)
Dizziness (grade 1-2, 3.2%)
Headache (grade 1-2, 1.1%)
Ventricular fibrillation (grade 1-2, 1.1%)
Sources:
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Disc. AE: Vertigo, Syncope...
AEs leading to
discontinuation/dose reduction:
Vertigo (1.35%)
Syncope (0.55%)
Postural hypotension (0.42%)
Headache (0.39%)
Nausea (0.46%)
Abdominal pain (0.35%)
Diarrhoea (0.16%)
CNS disorder (NOS) (0.14%)
Asthenia (0.19%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Malaise 2%
40 mg 1 times / day single, oral
Highest studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, mean age 27 years
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Sources:
Headache 6.7%
40 mg 1 times / day single, oral
Highest studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, mean age 27 years
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Sources:
Dizziness 8.9%
40 mg 1 times / day single, oral
Highest studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, mean age 27 years
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Sources:
Abdominal pain grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral
Recommended
Dose: 4.4 mg, 2 times / day
Route: oral
Route: multiple
Dose: 4.4 mg, 2 times / day
Sources:
unhealthy, mean age 62.6 years
Health Status: unhealthy
Age Group: mean age 62.6 years
Sex: M
Sources:
Diarrhoea grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral
Recommended
Dose: 4.4 mg, 2 times / day
Route: oral
Route: multiple
Dose: 4.4 mg, 2 times / day
Sources:
unhealthy, mean age 62.6 years
Health Status: unhealthy
Age Group: mean age 62.6 years
Sex: M
Sources:
Headache grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral
Recommended
Dose: 4.4 mg, 2 times / day
Route: oral
Route: multiple
Dose: 4.4 mg, 2 times / day
Sources:
unhealthy, mean age 62.6 years
Health Status: unhealthy
Age Group: mean age 62.6 years
Sex: M
Sources:
Ventricular fibrillation grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral
Recommended
Dose: 4.4 mg, 2 times / day
Route: oral
Route: multiple
Dose: 4.4 mg, 2 times / day
Sources:
unhealthy, mean age 62.6 years
Health Status: unhealthy
Age Group: mean age 62.6 years
Sex: M
Sources:
Dizziness grade 1-2, 3.2%
Disc. AE
4.4 mg 2 times / day multiple, oral
Recommended
Dose: 4.4 mg, 2 times / day
Route: oral
Route: multiple
Dose: 4.4 mg, 2 times / day
Sources:
unhealthy, mean age 62.6 years
Health Status: unhealthy
Age Group: mean age 62.6 years
Sex: M
Sources:
CNS disorder (NOS) 0.14%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Diarrhoea 0.16%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Asthenia 0.19%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Abdominal pain 0.35%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Headache 0.39%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Postural hypotension 0.42%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Nausea 0.46%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Syncope 0.55%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Vertigo 1.35%
Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources:
unhealthy, mean age 66.9 years
Health Status: unhealthy
Age Group: mean age 66.9 years
Sex: M
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: administration with ketoconazole increased alfuzosin Cmax and AUClast by, 2.3-fold and 3.2 fold, respectively; administration with diltiazem increased Cmax and AUC0-24 of alfuzosin 1.5-fold and 1.3-fold, respectively;
Page: 34
minor
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
The efficacy of alfuzosin treatment in patients with prostatism.
2001
Clinical significance of alpha1-adrenoceptor selectivity in the management of benign prostatic hyperplasia.
2001
Initial choices and final outcomes in lower urinary tract symptoms.
2001
Long-term aspects of medical treatment of BPH.
2001
Alfuzosin: overview of pharmacokinetics, safety, and efficacy of a clinically uroselective alpha-blocker.
2001 Dec
Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia.
2002
Tamsulosin: an update of its role in the management of lower urinary tract symptoms.
2002
Alfuzosin: a clinically uroselective alpha1-blocker.
2002 Apr
Long-term risk of re-treatment of patients using alpha-blockers for lower urinary tract symptoms.
2002 Apr
Pharmacokinetics and safety of a single oral dose of once-daily alfuzosin, 10 mg, in male subjects with mild to severe renal impairment.
2002 Dec
Finasteride in the treatment of clinical benign prostatic hyperplasia: a systematic review of randomised trials.
2002 Dec 12
The use of alpha-adrenoceptor antagonists in lower urinary tract disease.
2002 Feb
[Comparative evaluation of the effectiveness and safety of combined drug therapy of patients with benign prostatic hyperplasia with finasteride and alfuzozine].
2002 Jan-Feb
Alfuzosin, an alpha1-adrenoceptor antagonist for the treatment of benign prostatic hyperplasia: once daily versus 3 times daily dosing in healthy subjects.
2002 Jul
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia.
2002 Jul
[Chiral separation and preparation of three new antagonists of alpha 1-adrenoceptors by chiral mobile phase HPLC].
2002 Jun
Gateways to clinical trials.
2002 Oct
Randomised, placebo controlled, double blind study of alfuzosin SR in patients undergoing trial without catheter following acute urinary retention.
2002 Oct
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness].
2002 Sep
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results].
2002 Sep
Current treatment options for benign prostatic hyperplasia and their impact on sexual function.
2003 Apr
Safety and efficacy of alfuzosin 10 mg once-daily in the treatment of lower urinary tract symptoms and clinical benign prostatic hyperplasia: a pooled analysis of three double-blind, placebo-controlled studies.
2003 Aug
The Finnish version of The National Institutes Of Health Chronic Prostatitis Symptom Index correlates well with the visual pain scale: translation and results of a modified linguistic validation study.
2003 Aug
Use of alpha-blockers and the risk of hip/femur fractures.
2003 Dec
Safety and efficacy of alfuzosin 10 mg once-daily in the treatment of lower urinary tract symptoms and clinical benign prostatic hyperplasia: a pooled analysis of three double-blind, placebo-controlled studies.
2003 Dec
The evolution of detrusor overactivity after watchful waiting, medical therapy and surgery in patients with bladder outlet obstruction.
2003 Feb
Selective, sensitive and rapid liquid chromatography-tandem mass spectrometry method for the determination of alfuzosin in human plasma.
2003 May 25
[Pharmacologic treatment of benign prostatic hyperplasia].
2003 Sep 14
Priapism as a possible acute side effect of radical radiotherapy for prostate cancer.
2004 Apr
Comparative efficacy of two alpha-adrenoreceptor antagonists, doxazosin and alfuzosin, in patients with lower urinary tract symptoms from benign prostatic enlargement.
2004 Apr
Ejaculatory dysfunction and alpha-adrenoceptor antagonists.
2004 Aug
Drug approval highlights for 2003.
2004 Feb
Alfuzosin improves penile erection triggered by apomorphine in spontaneous hypertensive rats.
2004 Jan
Alfuzosin (uroxatral)--another alpha1-blocker for benign prostatic hyperplasia.
2004 Jan 5
Patients with bladder outlet obstruction who refuse treatment show no clinical and urodynamic change after long-term follow-up.
2004 Mar
The role of alpha-blockers in the management of acute urinary retention caused by benign prostatic obstruction.
2004 Mar
A comparison of the effects of tamsulosin and alfuzosin on neurally evoked increases in bladder neck and seminal vesicle pressure in rats.
2004 Mar
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia.
2004 Mar
New drugs of 2003.
2004 Mar-Apr
[The growth inhibition effect of alpha-adrenoceptor antagonists on androgen- independent prostate cancer cell line].
2004 May 22
Role of the newer alpha, -adrenergic-receptor antagonists in the treatment of benign prostatic hyperplasia-related lower urinary tract symptoms.
2004 Nov
Delayed complications of discontinuation of intrathecal baclofen therapy: resurgence of dyssynergic voiding, which triggered off autonomic dysreflexia and hydronephrosis.
2004 Oct
Alfuzosin-induced acute hepatitis in a patient with chronic liver disease.
2004 Sep
Clinical assessment of drug-induced QT prolongation in association with heart rate changes.
2005 Apr
Early symptom improvement of benign prostatic hyperplasia (BPH) treated with once daily alfuzosin.
2005 Aug
Symptom deterioration during treatment and history of AUR are the strongest predictors for AUR and BPH-related surgery in men with LUTS treated with alfuzosin 10 mg once daily.
2005 Aug
Evaluation of tamsulosin and alfuzosin activity in the rat vas deferens: relevance to ejaculation delays.
2005 Feb
The vasodilatory effect of alfuzosin and tamsulosin in passive orthostasis: a randomised, double-blind, placebo-controlled study.
2005 Mar
Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction.
2005 Mar
The clinical efficacy and tolerability of doxazosin standard and gastrointestinal therapeutic system for benign prostatic hyperplasia.
2005 Mar
Patents

Sample Use Guides

Usual Adult Dose for Benign Prostatic Hyperplasia
Route of Administration: Oral
In organ baths, isolated prostatic strips and isolated bladder strips were incubated with vehicle, tadalafil (10⁻⁶ M and 10⁻⁵ M), alfuzosin (3×10⁻⁸ M or 10⁻⁶ M and 10⁻⁵ M) or a combination. Concentration-response curves (CRCs) to norepinephrine were generated on prostatic strips and detrusor strips precontracted with carbachol. Strips were also submitted to electrical field stimulation (EFS). When alfuzosin and tadalafil were combined, the maximal relaxation to norepinephrine on carbachol-precontracted detrusor strips was significantly increased compared with tadalafil alone, and EFS-induced detrusor contractions were better inhibited compared with each compound alone. Tadalafil significantly inhibited norepinephrine-induced prostatic strip contractions by reducing the maximal effect, whereas alfuzosin shifted the CRC of norepinephrine to the right. Combining both tadalafil and alfuzosin resulted in a greater relaxant effect.
Name Type Language
ALFUZOSIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ALFUZOSIN [VANDF]
Common Name English
XATRAL
Brand Name English
ALFUZOSIN [HSDB]
Common Name English
2-FURANCARBOXAMIDE, (+/-)-N-(3-((4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)METHYLAMINO)PROPYL)TETRAHYDRO-
Systematic Name English
ALFUZOSIN [INN]
Common Name English
ALFUZOSIN [MI]
Common Name English
ALFUZOSIN [WHO-DD]
Common Name English
(+/-)-N-(3-((4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)(METHYL)AMINO)PROPYL)TETRAHYDROFURAN-2-CARBOXAMIDE
Systematic Name English
NSC-760065
Code English
Classification Tree Code System Code
WHO-ATC G04CA51
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
WHO-VATC QG04CA51
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
WHO-VATC QG04CA01
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
LIVERTOX 24
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
NDF-RT N0000175553
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
NDF-RT N0000000099
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
NCI_THESAURUS C29713
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
WHO-ATC G04CA01
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
Code System Code Type Description
DRUG BANK
DB00346
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
RXCUI
17300
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY RxNorm
INN
5357
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
FDA UNII
90347YTW5F
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
EVMPD
SUB05319MIG
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
MERCK INDEX
M1501
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
ALFUZOSIN
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
PUBCHEM
2092
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
IUPHAR
7109
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
CAS
81403-80-7
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
EPA CompTox
81403-80-7
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
HSDB
7290
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
DRUG CENTRAL
115
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
NCI_THESAURUS
C61627
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL709
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY
MESH
C047638
Created by admin on Fri Jun 25 21:51:53 UTC 2021 , Edited by admin on Fri Jun 25 21:51:53 UTC 2021
PRIMARY