U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H27N5O4
Molecular Weight 389.4488
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFUZOSIN

SMILES

COC1=CC2=NC(=NC(N)=C2C=C1OC)N(C)CCCNC(=O)C3CCCO3

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
Alfuzosin is a quinazoline-derivative alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Alfuzosin is marketed in the United States by Sanofi Aventis under the brand name Uroxatral. UROXATRAL (alfuzosin HCl extended-release tablets) is indicated for the treatment of the 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

2003
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
n = 45
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Population Size: 45
Sources:
Other AEs: Dizziness, Headache...
Other AEs:
Dizziness (8.9%)
Headache (6.7%)
Malaise (2%)
Sources:
4.4 mg 2 times / day multiple, oral (mean)
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
n = 93
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 62.6 years
Sex: M
Population Size: 93
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 45
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Population Size: 45
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
n = 45
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Population Size: 45
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
n = 45
Health Status: healthy
Age Group: mean age 27 years
Sex: M
Population Size: 45
Sources:
Abdominal pain grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral (mean)
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
n = 93
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 62.6 years
Sex: M
Population Size: 93
Sources:
Diarrhoea grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral (mean)
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
n = 93
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 62.6 years
Sex: M
Population Size: 93
Sources:
Headache grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral (mean)
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
n = 93
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 62.6 years
Sex: M
Population Size: 93
Sources:
Ventricular fibrillation grade 1-2, 1.1%
Disc. AE
4.4 mg 2 times / day multiple, oral (mean)
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
n = 93
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 62.6 years
Sex: M
Population Size: 93
Sources:
Dizziness grade 1-2, 3.2%
Disc. AE
4.4 mg 2 times / day multiple, oral (mean)
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
n = 93
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 62.6 years
Sex: M
Population Size: 93
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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
n = 13389
Health Status: unhealthy
Condition: benign prostatic hypertrophy
Age Group: mean age 66.9 years
Sex: M
Population Size: 13389
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: 34.0
minor
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
[Long-term therapy of benign prostatic hyperplasia. Our experience].
2001 Mar
Worldwide experience with alfuzosin and tamsulosin.
2001 Oct
Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia.
2002
Long-term risk of re-treatment of patients using alpha-blockers for lower urinary tract symptoms.
2002 Apr
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
Alfuzosin in the treatment of high leak-point pressure in children with neurogenic bladder.
2002 Nov
Randomised, placebo controlled, double blind study of alfuzosin SR in patients undergoing trial without catheter following acute urinary retention.
2002 Oct
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results].
2002 Sep
Clinical and pressure-flow changes after long-term treatment with alfuzosin SR.
2003
The evolution of detrusor overactivity after watchful waiting, medical therapy and surgery in patients with bladder outlet obstruction.
2003 Feb
Comparison of the relaxant effects of alfuzosin, phentolamine and sildenafil on rabbit isolated corpus cavernosum.
2003 Jun
Ejaculatory dysfunction and alpha-adrenoceptor antagonists.
2004 Aug
Drug approval highlights for 2003.
2004 Feb
Real life practice in the management of benign prostatic hyperplasia.
2004 Jan
[Can selective alpha-blockers help the spontaneous passage of the stones located in the uretero-bladder junction?].
2004 Jan-Mar
[A suggested treatment algorithm in nocturnal enuresis with emphasis on partial responders].
2004 Jul
Extended-release alfuzosin hydrochloride: a new alpha-adrenergic receptor antagonist for symptomatic benign prostatic hyperplasia.
2004 Mar
Delayed complications of discontinuation of intrathecal baclofen therapy: resurgence of dyssynergic voiding, which triggered off autonomic dysreflexia and hydronephrosis.
2004 Oct
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
Lower urinary tract symptoms suggestive of benign prostatic hyperplasia: latest update on alpha-adrenoceptor antagonists.
2005 Jun
Re: alfuzosin once daily facilitates return to voiding in patients in acute urinary retention.
2005 Mar
Efficacy and safety of two doses (10 and 15 mg) of alfuzosin or tamsulosin (0.4 mg) once daily for treating symptomatic benign prostatic hyperplasia.
2005 May
Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction.
2005 Nov
Alfuzosin for treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia: a systematic review of efficacy and adverse effects.
2005 Oct
A comparative study on the safety and efficacy of tamsulosin and alfuzosin in the management of symptomatic benign prostatic hyperplasia: a randomized controlled clinical trial.
2005 Sep-Oct
Patents

Sample Use Guides

Usual Adult Dose for Benign Prostatic Hyperplasia Extended-release tablet: 10 mg orally once a day immediately after the same meal each day
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 Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
WHO-VATC QG04CA51
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
WHO-VATC QG04CA01
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
LIVERTOX NBK548748
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
NDF-RT N0000175553
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
NDF-RT N0000000099
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
NCI_THESAURUS C29713
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
WHO-ATC G04CA01
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
Code System Code Type Description
NSC
760065
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
DRUG BANK
DB00346
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
RXCUI
17300
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY RxNorm
INN
5357
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
FDA UNII
90347YTW5F
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
EVMPD
SUB05319MIG
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
MERCK INDEX
m1501
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY Merck Index
DAILYMED
90347YTW5F
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
WIKIPEDIA
ALFUZOSIN
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
PUBCHEM
2092
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
IUPHAR
7109
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
CAS
81403-80-7
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID6048549
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
SMS_ID
100000087894
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
HSDB
7290
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
DRUG CENTRAL
115
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
NCI_THESAURUS
C61627
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL709
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
CHEBI
51141
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY
MESH
C047638
Created by admin on Sat Dec 16 17:16:56 GMT 2023 , Edited by admin on Sat Dec 16 17:16:56 GMT 2023
PRIMARY