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Details

Stereochemistry RACEMIC
Molecular Formula C19H27N5O4.ClH
Molecular Weight 425.91
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFUZOSIN HYDROCHLORIDE

SMILES

Cl.COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N(C)CCCNC(=O)C3CCCO3

InChI

InChIKey=YTNKWDJILNVLGX-UHFFFAOYSA-N
InChI=1S/C19H27N5O4.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H27N5O4
Molecular Weight 389.4488
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
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
Clinical significance of alpha1-adrenoceptor selectivity in the management of benign prostatic hyperplasia.
2001
Long-term aspects of medical treatment of BPH.
2001
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.
2001
Alfuzosin: overview of pharmacokinetics, safety, and efficacy of a clinically uroselective alpha-blocker.
2001 Dec
Efficacy and safety of once-daily alfuzosin in the treatment of lower urinary tract symptoms and clinical benign prostatic hyperplasia: a randomized, placebo-controlled trial.
2001 Dec
Do alpha-blockers prevent the occurrence of acute urinary retention?
2001 Mar
Worldwide experience with alfuzosin and tamsulosin.
2001 Oct
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms.
2002
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
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
[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
[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
Clinical and pressure-flow changes after long-term treatment with alfuzosin SR.
2003
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
Proceedings of the 99th meeting of the Food and Drug Administration Cardiovascular and Renal Drugs Advisory Committee. May 29th and 30th, 2003.
2003 Jun 17
First dose efficacy of alfuzosin once daily in men with symptomatic benign prostatic hyperplasia.
2003 Nov
Alfuzosin for the management of benign prostate hyperplasia.
2003 Nov
Alfuzosin treatment for chronic prostatitis/chronic pelvic pain syndrome: a prospective, randomized, double-blind, placebo-controlled, pilot study.
2003 Sep
Priapism as a possible acute side effect of radical radiotherapy for prostate cancer.
2004 Apr
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
[Can selective alpha-blockers help the spontaneous passage of the stones located in the uretero-bladder junction?].
2004 Jan-Mar
The role of alpha-blockers in the management of acute urinary retention caused by benign prostatic obstruction.
2004 Mar
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia.
2004 Mar
[The growth inhibition effect of alpha-adrenoceptor antagonists on androgen- independent prostate cancer cell line].
2004 May 22
New drugs 04. Part III.
2004 Sep
Prostate size influences the outcome after presenting with acute urinary retention.
2004 Sep
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
A pharmacoepidemiological approach to investigating inappropriate physician prescribing in a managed care setting in Israel.
2005 Feb
Re: Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention.
2005 Jul
Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH).
2005 Jun
Lower urinary tract symptoms suggestive of benign prostatic hyperplasia: latest update on alpha-adrenoceptor antagonists.
2005 Jun
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
The economic impact of using alfuzosin 10 mg once daily in the management of acute urinary retention in the UK: a 6-month analysis.
2005 Sep
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:32:30 GMT 2025
Edited
by admin
on Mon Mar 31 21:32:30 GMT 2025
Record UNII
75046A1XTN
Record Status Validated (UNII)
Record Version
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Name Type Language
UROXATRAL
Preferred Name English
ALFUZOSIN HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
ALFUZOSIN HYDROCHLORIDE [JAN]
Common Name English
ALFUZOSIN HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
SL-77499-10
Code English
ALFUZOSIN HYDROCHLORIDE [USAN]
Common Name English
ALFUZOSIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ALFUZOSIN HYDROCHLORIDE [MART.]
Common Name English
ALFUZOSIN HYDROCHLORIDE [MI]
Common Name English
ALFUZOSIN HCL
Common Name English
SL 77 499-10
Code English
ALFUZOSIN HYDROCHLORIDE [USP-RS]
Common Name English
ALFUZOSIN HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
Alfuzosin hydrochloride [WHO-DD]
Common Name English
SL-77-499-10
Code English
2-FURANCARBOXAMIDE, (±)-N-(3-((4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)METHYLAMINO)PROPYL)TETRAHYDRO-, MONOHYDROCHLORIDE
Common Name English
(±)-N-(3-((4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)METHYLAMINO)PROPYL)TETRAHYDRO-2-FURAMIDE MONOHYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C53408
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
SMS_ID
100000091802
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
USAN
NN-27
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
FDA UNII
75046A1XTN
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
DRUG BANK
DBSALT001063
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
DAILYMED
75046A1XTN
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
CAS
81403-68-1
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID3045514
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
EVMPD
SUB00340MIG
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
RXCUI
46043
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY RxNorm
RS_ITEM_NUM
1012917
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL709
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
PUBCHEM
71764
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
MERCK INDEX
m1501
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY Merck Index
CHEBI
32286
Created by admin on Mon Mar 31 21:32:30 GMT 2025 , Edited by admin on Mon Mar 31 21:32:30 GMT 2025
PRIMARY
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