ALFUZOSIN

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 Search

SMILES

COC1=CC2=C(C=C1OC)C(N)=NC(=N2)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

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	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf | https://www.drugbank.ca/drugs/DB00346

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-1a adrenergic receptor 67 Target ID: CHEMBL229 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9135028 \| https://www.ncbi.nlm.nih.gov/pubmed/10812954	Antagonist 2849	8.0 null [pKi]
Alpha-1b adrenergic receptor 45 Target ID: CHEMBL232 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9135028 \| https://www.ncbi.nlm.nih.gov/pubmed/10812954	Antagonist 2849	8.0 null [pKi]
Alpha-1d adrenergic receptor 37 Target ID: CHEMBL223 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9135028 \| https://www.ncbi.nlm.nih.gov/pubmed/10812954	Antagonist 2849	8.5 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
13.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
194 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
10 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
14% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087		inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP2A6 879 CYP1A2 2153	CYP1A2 1197	CYP1A 59 CYP2A6 86

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP2A6 911	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	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; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	minor

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_Pharmr_P1.pdf#page=27 Page: 27,28

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51141	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51141
ChemicalBook	CB4332422	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4332422
eMolecules	901348	https://www.emolecules.com/cgi-bin/more?vid=901348
MolPort	MolPort-003-666-623	https://www.molport.com/shop/molecule-link/MolPort-003-666-623

PubMed

Title	Date	PubMed
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	12887479
Use of alpha-blockers and the risk of hip/femur fractures.	2003 Dec	14641795
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	14632873
Alfuzosin hydrochloride for the treatment of benign prostatic hyperplasia.	2003 Jul 15	12892027
Estimated costs of treatment of benign prostate hyperplasia in Brazil.	2003 May-Jun	15745527
First dose efficacy of alfuzosin once daily in men with symptomatic benign prostatic hyperplasia.	2003 Nov	14624914
Alfuzosin for the management of benign prostate hyperplasia.	2003 Nov	14596659
Alfuzosin treatment for chronic prostatitis/chronic pelvic pain syndrome: a prospective, randomized, double-blind, placebo-controlled, pilot study.	2003 Sep	12946740
[Pharmacologic treatment of benign prostatic hyperplasia].	2003 Sep 14	14596018
A comparison of four different alpha1-blockers in benign prostatic hyperplasia patients with and without diabetes.	2004	15764250
Priapism as a possible acute side effect of radical radiotherapy for prostate cancer.	2004 Apr	15182410
Comparative efficacy of two alpha-adrenoreceptor antagonists, doxazosin and alfuzosin, in patients with lower urinary tract symptoms from benign prostatic enlargement.	2004 Apr	15049986
Ejaculatory dysfunction and alpha-adrenoceptor antagonists.	2004 Aug	15291886
A current review of medical therapy for benign prostatic hyperplasia.	2004 Feb	15038398
Drug approval highlights for 2003.	2004 Feb	14872168
Real life practice in the management of benign prostatic hyperplasia.	2004 Jan	15091049
Alfuzosin improves penile erection triggered by apomorphine in spontaneous hypertensive rats.	2004 Jan	14667526
Alfuzosin (uroxatral)--another alpha1-blocker for benign prostatic hyperplasia.	2004 Jan 5	14691408
[Can selective alpha-blockers help the spontaneous passage of the stones located in the uretero-bladder junction?].	2004 Jan-Mar	15688769
On call. My doctor gave me a prescription for Uroxatral to treat my enlarged prostate. I tried to look up this medicine in your Harvard Medical School Guide to Men's Health, but I couldn't find it. What can you tell me about Uroxatral?	2004 Jun	15210419
Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention.	2004 Jun	15126812
Extended-release alfuzosin hydrochloride: a new alpha-adrenergic receptor antagonist for symptomatic benign prostatic hyperplasia.	2004 Mar	15555475
Patients with bladder outlet obstruction who refuse treatment show no clinical and urodynamic change after long-term follow-up.	2004 Mar	15185815
The role of alpha-blockers in the management of acute urinary retention caused by benign prostatic obstruction.	2004 Mar	15036678
A comparison of the effects of tamsulosin and alfuzosin on neurally evoked increases in bladder neck and seminal vesicle pressure in rats.	2004 Mar	15008740
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia.	2004 Mar	14767264
New drugs of 2003.	2004 Mar-Apr	15098851
[The growth inhibition effect of alpha-adrenoceptor antagonists on androgen- independent prostate cancer cell line].	2004 May 22	15265404
Role of the newer alpha, -adrenergic-receptor antagonists in the treatment of benign prostatic hyperplasia-related lower urinary tract symptoms.	2004 Nov	15639685
Delayed complications of discontinuation of intrathecal baclofen therapy: resurgence of dyssynergic voiding, which triggered off autonomic dysreflexia and hydronephrosis.	2004 Oct	15224085
New drugs 04. Part III.	2004 Sep	15382384
Prostate size influences the outcome after presenting with acute urinary retention.	2004 Sep	15329112
Alfuzosin-induced acute hepatitis in a patient with chronic liver disease.	2004 Sep	15280514
Clinical assessment of drug-induced QT prolongation in association with heart rate changes.	2005 Apr	15903123
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	16098361
A pharmacoepidemiological approach to investigating inappropriate physician prescribing in a managed care setting in Israel.	2005 Feb	15726856
Evaluation of tamsulosin and alfuzosin activity in the rat vas deferens: relevance to ejaculation delays.	2005 Feb	15470085
Alfuzosin 10 mg once daily in the management of acute urinary retention: results of a double-blind placebo-controlled study.	2005 Jan	15667868
[The role of alpha1-adrenoblocker alfuzosine in diagnostic-therapeutic algorithm of hyperactive urinary bladder management in women and selection of patients for treatment with M-cholinergic antagonists].	2005 Jan-Feb	15776831
Re: Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention.	2005 Jul	15947706
Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH).	2005 Jun	15925080
Lower urinary tract symptoms suggestive of benign prostatic hyperplasia: latest update on alpha-adrenoceptor antagonists.	2005 Jun	15871733
The vasodilatory effect of alfuzosin and tamsulosin in passive orthostasis: a randomised, double-blind, placebo-controlled study.	2005 Mar	15716198
Re: alfuzosin once daily facilitates return to voiding in patients in acute urinary retention.	2005 Mar	15711385
Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction.	2005 Mar	15705088
The clinical efficacy and tolerability of doxazosin standard and gastrointestinal therapeutic system for benign prostatic hyperplasia.	2005 Mar	15705083
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	15839922
Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction.	2005 Nov	16217354
Alfuzosin for treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia: a systematic review of efficacy and adverse effects.	2005 Oct	16230138
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	16222890

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 `Wed Apr 02 08:56:13 GMT 2025` Edited by `admin` on `Wed Apr 02 08:56:13 GMT 2025`
Record UNII	90347YTW5F
Record Status	`Validated (UNII)`
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Name

Type

Language

XATRAL

Preferred Name

English

ALFUZOSIN

Official Name

English

ALFUZOSIN [VANDF]

Common 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